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The Obama Factor

A Q&A with historian David Garrow

by
David Samuels
August 02, 2023
Former President Barack Obama, who turns 62 tomorrow

Rick Friedman/Corbis via Getty Images

Former President Barack Obama, who turns 62 tomorrow

Rick Friedman/Corbis via Getty Images

Editor’s note: This piece is part of Tablet’s top 10 of 2023. Find the full list here. 

There is a fascinating passage in Rising Star, David Garrow’s comprehensive biography of Barack Obama’s early years, in which the historian examines Obama’s account in Dreams from My Father of his breakup with his longtime Chicago girlfriend, Sheila Miyoshi Jager. In Dreams, Obama describes a passionate disagreement following a play by African American playwright August Wilson, in which the young protagonist defends his incipient embrace of Black racial consciousness against his girlfriend’s white-identified liberal universalism. As readers, we know that the stakes of this decision would become more than simply personal: The Black American man that Obama wills into being in this scene would go on to marry a Black woman from the South Side of Chicago named Michelle Robinson and, after a meteoric rise, win election as the first Black president of the United States.

Yet what Garrow documented, after tracking down and interviewing Sheila Miyoshi Jager, was an explosive fight over a very different subject. In Jager’s telling, the quarrel that ended the couple’s relationship was not about Obama’s self-identification as a Black man. And the impetus was not a play about the American Black experience, but an exhibit at Chicago’s Spertus Institute about the 1961 trial of Adolf Eichmann.

At the time that Obama and Sheila visited the Spertus Institute, Chicago politics was being roiled by a Black mayoral aide named Steve Cokely who, in a series of lectures organized by Louis Farrakhan’s Nation of Islam, accused Jewish doctors in Chicago of infecting Black babies with AIDS as part of a genocidal plot against African Americans. The episode highlighted a deep rift within the city’s power echelons, with some prominent Black officials supporting Cokely and others calling for his firing.

In Jager’s recollection, what set off the quarrel that precipitated the end of the couple’s relationship was Obama’s stubborn refusal, after seeing the exhibit, and in the swirl of this Cokely affair, to condemn Black racism. While acknowledging that Obama’s embrace of a Black identity had created some degree of distance between the couple, she insisted that what upset her that day was Obama’s inability to condemn Cokely’s comments. It was not Obama’s Blackness that bothered her, but that he would not condemn antisemitism.

No doubt, Obama’s evolving race-based self-consciousness did distance him from Jager; in the end, the couple broke up. Yet it is revealing to read Obama’s account of the breakup in Dreams against the very different account that Jager offers. In Obama’s account, he was the particularist, embracing a personal meaning for the Black experience that Jager, the universalist, refused to grant. In Jager’s account, the poles of the argument are nearly, but not quite, reversed: It is Obama who appears to minimize Jewish anxiety about blood libels coming from the Black community. His particularism mattered; hers didn’t. While Obama defined himself as a realist or pragmatist, the episode reads like a textbook evasion of moral responsibility.

Whose version of the story is correct? Who knows. The bridge between the two accounts is Obama’s emerging attachment to Blackness, which required him to fall in love with and marry a Black woman. In Obama’s account, his attachment to Blackness is truthful and noble. In Jager’s account, his claims are instrumental and selfish; he grants particularism to the experience and suffering of his own tribe while denying it to others.

In evaluating the truthfulness of these two competing accounts, it seems worth noting that Jager is something more than a woman scorned by a man who would later become president of the United States. Obama asked her to marry him twice; she refused him both times, before going on to achieve her own high-level professional successes. A student of the great University of Chicago anthropologist Marshall Sahlins, Jager is a professor of East Asian Studies at Oberlin College whose scholarship on great power politics in Southeast Asia and the U.S.-Korean relationship is known for its factual rigor. In contrast, Dreams from My Father, as Garrow shows throughout Rising Star, is as much a work of dreamy literary fiction as it is an attempt to document Obama’s early life.

Scholarship aside, there is another reason to assume that Jager would be less likely to misremember an incident involving race and antisemitism than Obama. As it turns out, Jager’s paternal grandparents, Hendrik and Geesje Jager, were members of the Dutch resistance, whose role sheltering a Jewish child named Greetje in their home for three years led to their recognition as Righteous Among the Nations by Yad Vashem. In that context, at least, it seems quite likely that Jager would remember the particulars of a fight with Obama related to antisemitism, and be turned off by his response—while Obama’s version of the fight has the feel of an anecdote positioned, if not invented, to buttress the character arc of the protagonist of his memoir, which in turn positioned him for a career in public life.

Perhaps the most revealing thing about Jager’s account of her fight with Obama, though, is that not one reporter in America bothered to interview her before David Garrow found her, near the end of Obama’s presidency. As Obama’s live-in girlfriend and closest friend during the 1980s, Jager is probably the single most informed and credible source about the inner life of a young man whose election was accompanied by hopes of sweeping, peaceful social change in America—a hope that ended with the election of Donald Trump, or perhaps midway through Obama’s second term, as the president focused on the Iran deal while failing to address the concerns about rampant income inequality, racial inequality, and the growth of a monopoly tech complex that happened on his watch.

The idea that the celebrated journalists who wrote popular biographies of Obama and became enthusiastic members of his personal claque couldn’t locate Jager—or never knew who she was—defies belief. It seems more likely that the character Obama fashioned in Dreams had been defined—by Obama—as being beyond the reach of normal reportorial scrutiny. Indeed, Garrow’s biography of Obama’s early years is filled with such corrections of a historical record that Obama more or less invented himself. Based on years of careful record-searching and patient interviewing, Rising Star highlights a remarkable lack of curiosity on the part of mainstream reporters and institutions about a man who almost instantaneously was treated less like a politician and more like the idol of an inter-elite cult.

Yet when it came out six years ago, Rising Star was mostly ignored; as a result, its most scandalous and perhaps revelatory passages, such as Obama’s long letter to another girlfriend about his fantasies of having sex with men, read today, to people who are more familiar with the Obama myth than the historical record, like partisan bigotry. But David Garrow is hardly a hack whose work can or should be dismissed on partisan grounds. He is among the country’s most credible and celebrated civil rights historians—the author of The FBI and Martin Luther King, Jr. and Bearing the Cross (which won the Pulitzer Prize for Biography) and one of the three historian-consultants who animated the monumental PBS documentary Eyes on the Prize, as well as the author of a landmark history of abortion rights, Liberty and Sexuality.

In part, Garrow’s failure to gain a hearing for his revision of the Obama myth lay in his timing. Rising Star felt like old news the moment it was published in May 2017—as whatever insights the book contained were overtaken by the fury and chaos surrounding the beginning of Donald Trump’s presidency. As Trump’s incendiary carnival barker act took center stage, it was hard even for Republicans not to miss the contrast with Obama’s cerebral mannerisms and sedate family life. The idea that Obama was simply another self-obsessed political knife-fighter who played fast and loose with the truth didn’t resonate. In any case, Obama was now a footnote to history—a reminder of kinder, gentler times that the country seemed unlikely to see again anytime soon.

Yet there was also evidence to suggest that the idea Obama was no longer concerned with power or involved with power was itself part of a new set of myths being woven by and around the ex-president. First, the Obamas never left town. Instead, they bought a large brick mansion in the center of Washington’s Kalorama neighborhood—violating a norm governing the transfer of presidential power which has been breached only once in post-Civil War American history, by Woodrow Wilson, who couldn’t physically be moved after suffering a series of debilitating strokes. In the Obamas case, the reason for staying in D.C. was ostensibly that their youngest daughter, Sasha, wanted to finish high school with her class at Sidwell Friends. In June 2019, Sasha went off to college, yet her parents remained in Washington.

By then, it was clear to any informed observer that the Obamas’ continuing presence in the nation’s capital was not purely a personal matter. To an extent that has never been meaningfully reported on, the Obamas served as both the symbolic and practical heads of the Democratic Party shadow government that “resisted” Trump—another phenomenon that defied prior norms. The fact that these were not normal times could be adduced by even a passing glance at the front pages of the country’s daily newspapers, which were filled with claims that the 2016 election had been “stolen” by Russia and that Trump was a Russian agent.

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Given the stakes, then, it seemed churlish to object to the Obamas’ quiet family life in Kalorama —or to report on the comings and goings of Democratic political operatives and office-seekers from their mansion, or to the swift substitution of Obama as party leader for Hillary Clinton, who after all was the person who had supposedly been cheated out of the presidency. Why even mention the strangeness of the overall setup, which surely paled next to the raw menace of Donald Trump, who lurched from one crisis to the next while lashing out at his enemies and probably selling out the country to Vladimir Putin?

In a normal country, the exhaustive report issued in April 2019 by Special Counsel Robert Mueller, which uncovered no evidence that the 2016 election had been decided by Russian actions, let alone that Trump was a Russian agent, might have been a cue for the Obamas to go home, to Chicago, or Hawaii, or Martha’s Vineyard. The moment of crisis was over. Russiagate turned out to have been a politically motivated hoax, just as Trump had long insisted.

But while the attention of Republicans in Washington turned to questioning the FBI, more careful observers could not fail to notice that the FBI had hardly acted alone. After all, Russiagate had not originated with the Bureau, but with the Clinton campaign, which having failed to get even sympathetic mainstream media outlets like The New York Times and The Washington Post to bite on its fantastical allegations, was reduced to handing off the story to campaign press apparatchiks like Slate’s Franklin Foer and Mother Jones’ David Corn. The fact that the story only got bigger after Clinton lost the election was due to Obama’s CIA director, John Brennan, who in November and December of 2016 helped elevate Russiagate from a failed Clinton campaign ploy to a priority of the American national security apparatus, using a hand-picked team of CIA analysts under his direct control to validate his thesis. If Brennan was the instrument, the person who signed the executive order that turned Brennan’s thesis into a time bomb under Trump’s desk was Barack Obama.

The election of Joe Biden in 2020 gave the Obamas even more reasons to stay in town. The whispers about Biden’s cognitive decline, which began during his bizarre COVID-sheltered basement campaign, were mostly dismissed as partisan attacks on a politician who had always been gaffe-ridden. Yet as President Biden continued to fall off bicycles, misremember basic names and facts, and mix long and increasingly weird passages of Dada-esque nonsense with autobiographical whoppers during his public appearances, it became hard not to wonder how poor the president’s capacities really were and who was actually making decisions in a White House staffed top to bottom with core Obama loyalists. When Obama turned up at the White House, staffers and the press crowded around him, leaving President Biden talking to the drapes—which is not a metaphor but a real thing that happened.

That Obama might enjoy serving as a third-term president in all but name, running the government from his iPhone, was a thought expressed in public by Obama himself, both before and after he left office. “I used to say if I can make an arrangement where I had a stand-in or front man or front woman, and they had an earpiece in, and I was just in my basement in my sweats looking through the stuff, and I could sort of deliver the lines while someone was doing all the talking and ceremony,” he told Steven Colbert in 2015, “I’d be fine with that because I found the work fascinating.” Even with all these clues, the Washington press corps—fresh off their years of broadcasting fantasies about secret communications links between Trump Tower and the Kremlin—seemed unable to imagine, let alone report on, Obama’s role in government.

David Garrow
David Garrow

Tribune Content Agency LLC/Alamy

Instead, every few months a sanitized report appears on some aspect of the ex-president’s outside public advocacy, presented within limits that are clearly being set by Obama’s political operatives—which conveniently elide the problems that are inherent in having a person with no constitutional role or congressional oversight take an active role in executive decision-making. Near the end of June, for example, Politico ran a long article noting Biden’s cognitive decline, with the coy headline “Is Obama Ready to Reassert Himself?”—as if the ex-president hadn’t been living in the middle of Washington and playing politics since the day he left office. Indeed, in previous weeks Obama had continued his role as central advocate for government censorship of the internet while launching a new campaign against gun ownership, claiming it is historically linked to racism. Surely, the spectacle of an ex-president simultaneously leading campaigns against both the First and Second Amendments might have led even a spectacularly incurious old-school D.C. reporter to file a story on the nuts and bolts of Obama’s political operation and on who was going in and out of his mansion. But the D.C. press was no longer in the business of maintaining transparency. Instead, they had become servants of power, whose job was to broadcast whatever myths helped advance the interests of the powerful.

There is another interpretation of Obama’s post-presidency, of course—one shared by many Republicans and Democrats. In that interpretation, Obama was never the leader of much of anything, neither during the Trump years nor now. Instead, he was focused on buying trophy properties, hanging out with billionaires, and vacationing on private yachts while grifting large checks from marks like Spotify and Netflix—even if his now-stratospheric levels of personal vanity also demanded that every so often he show up President Biden for the sin of occupying his chair in the White House. 

In the absence of what was once American journalism, it is hard to know which portrait of Obama’s post-presidency is truer to life: Obama as a celebrity-obsessed would-be billionaire, or as a would-be American Castro, reshaping American society from his basement, in his sweats.

Yet the answer is, I believe, somewhere in David Garrow’s book.

At bottom, Rising Star is a tragic story about a young man who was deeply wounded by the abandonment of both his white mother and his Black father—a wound that gifted him with political genius and at the same time made him the victim of a profound narcissism that first whispered to him in his mid-twenties that he was destined to be president. It is not hard to see how Garrow has come to believe that Obama’s ambition proved to be toxic, both for the man and for the country. But why?

As a human being who was sentient for long stretches of time between 2008 and 2017, I was, in general, a fan of Barack Obama and his presidency. What I could never understand was Obama’s contempt for the idea of American exceptionalism. Even as president, Obama insisted on poking exceptionalists in the eye, saying that he believed in American exceptionalism “just as I suspect that the Brits believe in British exceptionalism and the Greeks believe in Greek exceptionalism.” Why would the president of the United States feel the need to disabuse his countrymen of the idea that they are special?

What made Obama’s rejection of American exceptionalism seem particularly weird to me was his attachment to Abraham Lincoln, whose cadences and economy of language he urged his speechwriters to emulate. As a historian, one might plausibly argue that Lincoln was a saint who saved the Union or a monster who shed rivers of blood—or that he didn’t go far enough. But there is no arguing with Lincoln’s belief in the uniqueness of the American destiny, for which he sent hundreds of thousands of young men to die. Of all men, Abraham Lincoln would have been baffled by an American president who denied that America was exceptional. What did all those people die for, then? And what exactly did Obama think that Lincoln’s speeches were about?

Obama’s hostility to American exceptionalism also seemed linked to his hostility to Israel, or more specifically to America’s identification with Israel, which finally resulted in his determination during his second term to reach his agreement with Iran—an agreement with the main objective of integrating that country into America’s security architecture in the Middle East, while limiting Israel’s power in the region. Again, why?

The sheer amount of political capital and focus Obama put into achieving the JCPOA during his second term, to the near-exclusion of other goals, suggests that the deal was central to his politics. It also carries more than a whiff of the kind of politics in which the American Empire is seen not just as unexceptional, but also, in some ways, as actively evil. It was a politics born out of the confluence of the Vietnam War and the civil rights movement, which saw a racist war abroad being used to protect a racist power structure at home. That old alliance of civil rights, anti-imperialism, and identity politics made the Democratic Party that Obama positioned himself to lead—college-educated, corporate-controlled—seem cool, allowing it to use post-1960s radical ideology as a language to sell stuff.

In a passage of Dreams that reeks of neo-liberal poser-ism, Obama recalls, “I chose my friends carefully. The more politically active Black students. The foreign students. The Chicanos. The Marxist professors and structural feminists and punk-rock performance poets. We smoked cigarettes and wore leather jackets. At night, in the dorms, we discussed necolonialism, Franz Fanon, Eurocentrism, and patriarchy. When we ground out our cigarettes in the hallway carpet or set our stereos so loud that the walls began to shake, we were resisting bourgeois society’s stifling constraints. We weren’t indifferent or careless or insecure. We were alienated.”

But was Obama truly guided by post-1970s dorm-room stoner politics (as Garrow shows, Obama’s best friend at Harvard Law School was a white student named Rob Fisher who is now a senior special counsel at the Securities and Exchange Commission, that famed hotbed of punk-rock performance poets and structural feminists), or was he driven by some deeper radicalism?

My own read of Obama has always been that he was a skillful elite-pleaser with a radical streak that did in fact emerge from the anti-imperialist politics of the 1970s, the foundational claim of which was that equality trumps freedom. Which brings us back to Obama’s breakup with Sheila Miyoshi Jager.

I have never seen any evidence that Barack Obama has the slightest personal animus toward Jews as individuals. But from his denial of American exceptionalism, and his sourness toward Israel, going all the way back to Sheila Miyoshi Jager’s account of their breakup, there does seem to be an awareness of the underlying problem posed to his politics by Jews—that is, the problem posed by Jewish group survival and their continuing insistence on Jewish historical particularity.

Progressive theology is built on a mythic hierarchy of group victimhood which has endured throughout time, up until the present day; the injuries that the victims have suffered are so massive, so shocking, and so manifestly unjust that they dwarf the present. Such injuries must be remedied immediately, at nearly any cost. The people who do the work of remedying these injustices, by whatever means, are the heroes of history. Conversely, the sins of the chief oppressors of history, white men, are so dark that nothing short of abject humiliation and capitulation can begin to approach justice.

It goes to say that nothing about the terms of progressive theology is original. It is the theology of Soviet communism, with class struggle replaced by identity politics. In this system, Jews play a unique, double-edged role: They are both an identity group and a Trojan horse through which history can reenter the gates of utopia.

Ghettos were invented for Jews. Concentration camps, too. How can Jews be “privileged white people” if they are clearly among history’s victims? And if Jews aren’t white people, then perhaps lots of other white people are also victims and therefore aren’t “white,” in the theological sense in which that term gains its significance in progressive ideology. Maybe “Black people” aren’t always or primarily Black. Maybe the whole progressive race-based theology is, historically and ideologically speaking, a load of crap. Which is why the Jews are and will remain a problem.

Obama didn’t invent any of this stuff; he was just a wounded kid trying to figure out his own place in the world and get ahead. Still, looking back, it is hard to avoid the sense that Obama himself was exceptional. He was the guy chosen by history to put something in the American goldfish bowl that made all the fish go crazy and eat each other: America’s emerging oligarachy cementing its grip instead of going bust. The rise of monopoly internet platforms. The normalization of government spying on Americans. Race relations going south. Skyrocketing inequality. The rise of Donald Trump. The birth of Russiagate. It all happened with Obama in the White House.

To understand how we wound up here, it therefore seems necessary to start by understanding the man that so many of us refused to see outside of the myth that he created for himself. His problems are now our problems, as much as Donald Trump’s are.

That is why I went to talk to David Garrow.

What follows is a condensed and edited version of two long interviews conducted recently with the historian at his home in Pittsburgh, centering around his 2017 biography of Barack Obama, Rising Star.

Martin and Barack

David Samuels: At this point, the number of people involved in America’s civil rights struggle and politics you have interviewed must be in the thousands, right?

David Garrow: I would think it’s close to 2,000. The Obama book alone was 1,000-plus.

In general, do you find a large gap between people’s impression of their truthfulness as they speak and the reality of what you find once you start checking?

People remember happy memories very well. They purge painful memories. This is true of everybody in Montgomery, everybody who was active in the boycott. And now the children of the boycott are my age. I got a wonderful email yesterday from Sharon Campbell Waters, whose daddy ran part of the carpool operation, sending me these pictures of Alabama State U, renaming a dorm in honor of Mrs. JoAnn Robinson—the woman who actually started the boycott, whose memoir I got published.

So, everybody remembers December of ‘55 to December of ‘56 very well. Then, in Montgomery, nothing much happens in ‘57, ‘58, ‘59: King’s spending too much time traveling around, the Montgomery Improvement Association isn’t doing much, SCLC [Southern Christian Leadership Conference] is sort of stillborn, and various people in the MIA are sniping at each other. Ed Nixon’s really unhappy. Mrs. Parks has to leave and move to Detroit.

I became convinced in the early ’80s that lawyers have the worst memories, which was perhaps overinformed by Burke Marshall, the Kennedy civil rights guy, who once asked me, “Remind me, did Albany happen before Birmingham? Or did Birmingham happen before Albany?” I’m thinking, “Hmm.” E.D. Nixon from Montgomery is the stellar example of people who reimagine a fictional past in which they played more decisive roles than they actually did: Mr. Nixon did not choose King to head the boycott.

If I use the universe of people from the Obama book—and granted that’s a whole lot closer in time—most of the memories there checked out pretty well. But Barack himself is unable to remember or acknowledge where he had shortcomings or failures.

You interviewed Obama when he was in the White House?

I spent eight hours talking with him on three different days. And we didn’t record it, and it’s officially off the record, but some of the stuff he was most energized about was, to me, hilariously inconsequential. Like, insisting that he really had been fluent in Indonesian as a third grader, or that he didn’t tell several Illinois State Senate staffers that he knew Rickey Hendon could kick his butt. There are shared elements in the sensitivities.

What do you see as the connection, if any, between the personal lives of powerful men and their public lives, based on your years of research on Dr. King, and your experience writing about Obama?

I think one can in large part, in King’s case, say these were sort of two separate lives. Because he lived it that way. He lived it as two separate lives.

Might one make the same case about Obama, but in reverse? It seems clear that Obama leads an exemplary, highly controlled private life, consuming exactly seven almonds while watching The Man in the High Castle or Draymond Green highlights on ESPN for stress relief.

Right. Yes.

In fact, I can make the case that Obama’s public life was the amoral part, beginning with the toleration of genocide in Syria and the extrajudicial killing of U.S. citizens, and extending to wide-scale illegal surveillance and spying, and his now becoming the spokesperson for gutting the First Amendment in favor of government censorship of large tech platforms.

The defense of the Obama people when you talk to them is he was never touched by scandal, meaning personal scandal. And you’re like, “Well, I’m sure all those people who got gassed to death in Syria or are growing up in American towns with no jobs feel just great about the fact that he never got a blow job in the Oval Office.”

I think a major turning point in his presidency was that whole thing where he and Denis McDonough walk around the White House grounds and he changes his mind about Syria.

I don’t think Denis is a reliable narrator. That’s his chief of staff, and that’s too much of a recognizably made-for-TV moment, a Bob Woodward moment, for me to buy it. Nor does it fit with the strategic architecture that Obama had already committed himself to. Sure, maybe Obama suddenly remembered while taking a walk in the Rose Garden that his big second-term goal was to do a nuclear deal with Iran, and that he had written Khamenei a letter recognizing Syria as an Iranian equity. But I doubt that.

We’ve got these other people who were convinced he was going to do it.

I imagine that part of being effective as president is convincing everyone within your own administration that you are at least conceivably on their side. But there’s no way to bomb Syria—meaning, to bomb Iran—and also convince Iran that he was sincere about reaching a deal. He just let all the bomb Syria talk go on as long as he could to please the hawks, before pulling the rug out from under them. That’s politics.

Barack Obama meets with Deputy National Security Advisor for Strategic Communications Denis McDonough (right) and speechwriter Ben Rhodes on Air Force One June 4, 2009 on route to Cairo, Egypt
Barack Obama meets with Deputy National Security Advisor for Strategic Communications Denis McDonough (right) and speechwriter Ben Rhodes on Air Force One June 4, 2009 on route to Cairo, Egypt

Pete Souza/The White House via Getty Images

I didn’t read anything beyond the simple daily coverage of this during those years, but I always assumed that his discomfort with the Israeli government was, in significant part, just a reaction to Netanyahu and disliking Netanyahu as an individual character.

I once spent two and a half hours alone in a room with Bibi Netanyahu, and they were among the two and a half most excruciatingly boring hours of my life. At one point he was reciting verbatim long passages from Margaret Thatcher’s memoirs. I doubt Barack Obama would have enjoyed that much. Though I do kind of cherish the idea of Bibi and Obama in the same room, each competing in an effort to demonstrate that they are each indeed the most brilliant person on earth. The other big thing they have in common, aside from their belief in their own genius, is that they are both products of the periphery of the American empire.

So, do people shape history? Do individuals matter?

God, yes—for the worse. Millions of people have had their lives messed up because of Vladimir Putin. Would the Nazi regime and the Holocaust have happened without Hitler? No. Hermann Goering, Rudolf Hess, Heinrich Himmler, those clowns could not have created something. At the same time that I have this bizarre fascination with supremely evil characters like Putin and Hitler, I also have a somewhat parallel fascination with people who have remarkable courage, even though they’re getting almost no support for it. Alexei Navalny, first and foremost. He has some inner strength that exceeds even Doc’s.

Yet Doc [Martin Luther King] always believed that he was not essential, that he was accidental, and that if he hadn’t ended up as him, that Ralph Abernathy or Fred Shuttlesworth or someone else would’ve been him instead.

Do you think that’s true?

Yeah, in the big picture sense. Because if we go back to Montgomery, the boycott would’ve happened without Doc. Would it necessarily have been such a grand success? No.

How essential is the quality and tenor of his speech that night of Dec. 5 at Holt Street? You can argue the inevitability of the boycott; you can also argue, particularly about Holt Street, that that set the tenor for it, that his whole grounding in a biblical doctrine of love gave the entire enterprise its nonviolent, non-hateful quality. But once we get past the success of the boycott period, 12, 13 months, and we go through those fallow three years, the sit-ins would’ve happened, the Freedom Rides certainly happened without Doc. What Fred was doing in Birmingham would’ve happened without Doc.

Doc’s essential nature is, to a significant degree, because the white press elevates him. The press makes him this symbol, and as I say in BTC [Garrow’s Pulitzer Prize-winning Bearing the Cross], he realizes this is not really him, that there’s him and there’s this projection.

Let me say one other thing. Doc always 100 percent retained his individual self, even while realizing that there was this press creation. And when he’s wearing that uniform of the black suit, little tie, and he’s being so relentlessly sober whenever he’s in the public eye, that’s not him. That’s him playing the part that he’s been called into.

With Barack, I’m not sure I like the word binary, but with Doc, Doc was very clear about himself and the role. With Barack, there’s an extent of intertwining, there’s an absence of keeping the two selves separate.

But there is a before-and-after moment, which Obama writes about in Dreams and which you document in your book: Obama coming to Chicago, and his conversation with this motel owner when he crosses the state line.

Yes, that is not there when he drives to Chicago. Bob Elia, the motel owner up there, I found him because of Marc Silverman, our wonderful law librarian at Pitt Law. Marc went back in the property records for Sharon, Pennsylvania, and told me who owned the motel where Obama stays, which he writes about in Dreams. And so, I found four phone numbers for Robert Elia—right on that Pennsylvania-Ohio border.

I love your description of talking to Elia on the phone. But the person who actually witnesses this transformation, in which Obama becomes the person we know now, and when he begins to imagine that he has this special destiny—which turns out to be true—is his girlfriend, Sheila Miyoshi Jager.

Sheila had a huge impact on me because no one can appreciate the difference between who he was and who he became the way she can.

She was poised at exactly the point of inflection, in a very intimate space, just the two of them sharing this apartment in Chicago. She saw the transformation happen.

Sheila was so mortified when I found those comments she posted on those various Washington Post stories, because she’s even more of an innocent, by a long stretch, than I am. She had no idea that mouthing off when you’re logged in means that anyone can identify who posted this comment.

At some point as president, Barack starts calling Sheila, his girlfriend at the University of Chicago and later a professor at Oberlin—one of his three girlfriends before he marries Michelle and reestablishes a connection with her. I imagine that happened because he knew you had found her in your research for your book. Did he talk to you about that directly?

Yeah.

I assume he was not happy.

Oh no. This is where I don’t necessarily trust my memory, but I think I already knew that from Bob Bauer, Obama’s lawyer, who was my go-between with Barack for months. I could not be more professionally positive about Bob Bauer. He handled an incredibly difficult, bizarre situation superbly.

Why was it bizarre?

It was bizarre to me because—and again, no one’s ever challenged me on this, and as with the Dorothy Cotton thing [Dr. King’s mistress], it was seemingly an odd decision—it was easy and automatic to let Barack read the whole typescript of the first 10 chapters and mark it up, which is what then leads to these long discussions of, “Yes, I was fluent in …” whatever you call it, Indonesian.

Bob is Barack’s lawyer, but he was also coaching me. My clearest memory, and there’s nothing officially off the record with Bob, so I think I can say this, and boy, it’s the clearest thing I remember of all my conversations with Bob. … This is close to a quote: “Whatever you do, don’t ask him about his father.”

From the author of Dreams from My Father, that’s very strange.

He’s not normal—as in not a normal politician or a normal human being.

All the President’s Women

How did you get those three women, Obama’s college and law school girlfriends, to give you Obama’s love letters to them, and what was the most surprising thing you found in them?

With Alex [McNear, Obama’s girlfriend at Occidental College], I think she wanted to have her role known. So when Alex showed me the letters from Barack, she redacted one paragraph in one of them and just said, “It’s about homosexuality.”

And then sometime, right about when Rising Star came out, Alex indirectly sold the original, sold those letters, and they ended up at Emory. So Emory put out a press release saying, “We’ve gotten these rare letters by Barack Obama.” And no mention of this paragraph that was too sensitive. None of the papers mentioned it. Emory didn’t mention it.

So I sent one of my oldest friends, Harvey Klehr—Harvey was the guy going back to 1980 when I was trying to solve who fingered [Dr. King’s close advisor] Stanley Levison, how was it known to the FBI that Stan had been …

A communist.

Yes. So I emailed Harvey, said, “Go to the Emory archives.” He’s spent his whole life at Emory, but they won’t let him take pictures. So Harvey has to sit there with a pencil and copy out the graf where Barack writes to Alex about how he repeatedly fantasizes about making love to men.

Now, Genevieve [Cook, Obama’s girlfriend in New York], Genevieve’s just a free spirit. I went to Australia to meet her. And she had had a—let me think about how best to say this—she had a subsequent relationship there in Australia that was troubled, and so she was living in a very low-visibility context. So we drove down and stayed with her and her partner for three days in the Mornington Peninsula south of Melbourne. And she was keeping a journal during her relationship with Barack, so she had all sorts of stuff.

Sheila, though, it’s unclear.

What became of Alex?

Alex, I haven’t heard from in about two years. There’s a wonderful woman named Margot Mifflin who was part of that whole crowd, who teaches journalism at CUNY. Margot and her husband, they’re sort of the most active of the Oxy [Occidental] crowd.

Now, Alex was living in … I’m not very good on the Hamptons, is Sag Harbor right? Her mother was alive then. I think when she sold the letters to Emory, her excuse was that she needed money to help out with the mother’s medical conditions. I have a very clear memory of Alex being embarrassed about selling the letters.

But I can’t line up chronologically when that was in time related to when Barack starts calling Sheila again.

Do you think that he starts calling her again because he needs to keep her close because she knows too much of his story, and she becomes a wild card if she no longer feels a tie to him?

I think that’s accurate.


How did you find Sheila?

When I start reading about Barack in early ’08, I read Dreams and thought, “This is a crock.” It’s not history. It’s all make-believe. Who knows what the real story is?

And initially for some number of months, I thought I was only going to do a magazine article on Barack’s community-organizing years—nothing more than 8,000 words, or what have you. But it was clear from the campaign journalism that Barack had lived with a graduate student in Hyde Park during those years. But no journalist ever goes to try to locate this former graduate student he lived with, which was weird. Anyone who’s ever been in a university knows you can go find a student directory that’s going to have people’s addresses.

So I sent my research assistant Alix Lerner to do this at Regenstein Library. She pulls off this dusty old student directory from 1987-88. And we not only find Sheila, we find this nice couple who are both at NC State in Raleigh who lived upstairs from them, and who would see them in the laundry room. So there it is, in this student directory: Sheila Miyoshi Jager.

I emailed her. Sheila’s easy to find. She was then a professor at Oberlin. This was sometime in ‘09. And, oh boy, I have a very conscious, extremely strong memory of how much emotional strain I was under as she sending me all of these confessional emails. Oh wow.

Why did you feel it as an emotional strain?

Because it’s clear she’s under incredible stress. I mean, her first email to me was, “I’m so happy that you are the person who’s discovered me.” She had had one or two experiences with the Daily Mail ; somebody had left her a message. And then there was some other woman in that graduate-student circle whose name was also Sheila, who’d gotten a call because somebody had told somebody that they thought his girlfriend was named Sheila. So somebody focuses on this wrong woman, who’s, like, a lawyer in San Francisco.

I mean, one would think that there’d be a journalist in America who would go look at the student directory in the University of Chicago Library in 2008.

Well, you know why there wasn’t one, right?

Yeah. “We’re looking for the Black guy’s white girlfriend.”

I mean, why go through all that trouble to be labeled a racist and lose your job.

Both with that, and with all the unpleasant stuff about Doc that was in the NARA document dump in 2018, I don’t perceive the existence of having a choice.

Barack’s love letters to Alex, if they are actually love letters, are hard to read. Not just because they’re so poorly written, but because of the clear lack of any human interest in the person he’s writing to. The letters are completely performative. She may as well have been a tree or some kind of theater backdrop. Maybe all young men are guilty of this fault, but these examples seem pretty egregious.

It’s pretty clear to me, and this is me putting little pieces together with Alex and with Sheila, but I’m 97 percent convinced that Barack either drafted all those letters in his journal and then made them into letters, or he wrote the letters and then copied them into the journal.

The first time—again, I can say this—the first time I saw him at the White House in the Oval, he’s sitting in that usual chair back at the fireplace. I’m at the right end of that, the couch that’s facing toward Lewinsky territory. And over on the desk, the only thing on the desk is this big pile of all his journals over the years. And he’s arranged it this way on purpose—to show me that he has them, and so he can tell me that I can’t see them. He’s got this big sack, I want to call it a cloth sack or a canvas sack, in the bottom of which are the journals. And then on the top of it is the typescript printout of my manuscript. So he’s carrying them around together.

The letters to and from Sheila. Are we ever going to see them? Not in my lifetime or yours. Certainly not in Barack’s lifetime will those journals see the light of day. I wouldn’t be astonished if he burns them.

Why? What can’t he let anyone see?

He wants people to believe his story. For me to conclude that Dreams from My Father was historical fiction—oh God, did that infuriate him.

I’ve gotten the sense, from my read of him and from people close to him, that the pose of being a writer is actually one that he prefers in many ways to being a politician.

Oh God, yes. Yes, yes, yes.

So why wouldn’t he want his writerliness to be revealed?

He doesn’t want the writerliness challenged. It’s my story and I’m sticking to it. The book [Dreams] is so fictionalized.

What’s wrong with that? At this point in time, only a very naive person would think of memoir as anything other than a literary genre that is cousin to the novel. It’s not history.

It’s so inaccurate, whether about the dynamics among the guys in Hawaii or what’s going on in the community group on the far South Side. And it completely omits women. I’ve always thought that there’d eventually be a feminist critique of Obama because his mother and all the girlfriends—they’re not there. They don’t exist.

I will say, from reading your book, I had the sense that all of those women seemed like they felt betrayed by him. Even the act of giving you his love letters is itself a tremendously aggressive, hostile act. They knew exactly what his response would be. They knew what they had.

With Alex and Genevieve, it was so far in the past. Sheila is a whole different thing.

With Sheila, you could feel the hurt, but with Alex, you could too. The anecdote that obviously came from Alex about running into Barack and Michelle in Boston or New York on a street—

On Madison Avenue. Yes, yes, yes, yes, yes.

There’s a million ways to be like, “Hi, this is Alex. She’s an old friend from school.” And then, your significant other may say later on, “Oh, did you fuck her?” You say, “Oh, no.” Or “Yes.” Or whatever.

But you don’t cross the street.

“I Have a Dream” Meets Dreams

So is Barack Obama the prime mover in the transformation of the American society we are living through now? Or was he simply a mannered observer, or a huge narcissist who couldn’t care less about anything outside himself? You wrote the best of the Obama books, you wrote one of the best King books … I understand the mesh of techniques that you use. I am hoping you can help enlighten me.

I’m entirely certain that I understand Doc. I understand Doc far better than I understand Barack because Doc, even though he was so consistently disciplined in public, was otherwise, to people who knew him well, a completely transparent person—in his strengths, his weaknesses, and his failures.

This looms so huge to me, and I work at how to best articulate it: When I first started meeting the King people in September ‘79, I was 26 years old, and I had no ability to appreciate how close in time I was to 1968. It didn’t seem close to me. I can picture the first time I met Dorothy Cotton. I can picture Dorothy’s house, and I don’t want to get off on this, but I should say it: The most profound decision I’ve ever made was to protect Dorothy both in the FBI book and in BTC. Because it was her very clear wish that she didn’t want to be painted or pigeonholed as just Dr. King’s, you know—it’s a word that begins with M.

And I won’t even use that word because a lot of us, not in public, have called Dorothy the real wife. And having known Dorothy and having known Coretta, it was eminently obvious to me why someone as needy of solace as Doc would spend more time with Dorothy.

Thanks to that NARA document dump from the JFK Records Act four years ago now, I know a whole lot more of the details in the understory now than I did in 1986. I’ve always expected someone to challenge me on why I protected Dorothy. But to me, it came very easily. I’ve never doubted myself about it. But back when I first heard about Dolores Evans and Chrystal, way back in ‘85 or so, I didn’t believe it was true. I thought it was very unlikely to be true because I understood that it was mainly coming from Don Newcomb and that Newcomb was an alcoholic. So I wrongly thought it was some guy talking in his liquor.

With Rising Star, without any question, how to deal with Alex and Genevieve and especially with Sheila was the most professionally demanding thing I’ve ever been through.

I remember the first time I was struck by Obama as being a personality who existed outside the normal confines of American politics was when I went out to Denver for his acceptance speech in 2008.

I think Barack in that winter of ‘08, ‘09, realized there was no way that his presidency could actually live up to the expectations. And I think even the fanboy journalists would acknowledge, under a little bit of pressure, that it ended up being an underwhelming, disappointing presidency. It will, in the long run, be seen as a failed presidency because of the international failures.

There was also a moment in The Audacity of Hope, which I wrote about in 2008, of a warning: Whatever happens next is on you people, not me. And I was like, that is, on one hand, a stunningly honest and upfront thing to say. It’s also a complete abandonment or rejection of the responsibility that he should be embracing in this moment.

I wouldn’t even say I was troubled by it. I was baffled by it. What does it mean? Who is this guy, and where is this guy coming from? I went back and re-read “Dreams from my Father,” which I bought when it came out, and I came upon the passage where his stepfather, Lolo Soetoro, takes him out into the backyard in Indonesia and teaches him how to fight. And I said, “Wait a minute. I know this scene. Where’s it from?” And then I went back and found the battle royale scene in Invisible Man.

Right, right, right.

And, of course, Ellison’s Invisible Man ends up in a basement by himself, which is how the book begins. But the point of Dreams from My Father is that Obama is going to do the opposite. Instead of ending up in a basement with a bunch of light bulbs and his Louis Armstrong records, he’s going to become the person who will effect large-scale social change here in America. And again, I was like, “What a weirdly writerly thing to do.” This is clearly a highly wrought literary work of self-fashioning by a person who is in dialogue with literary sources. Or, to put it another way: I’m watching this guy make himself up.

It was funny, when I was with Ben Rhodes in the White House, one of the things that Rhodes was at pains to get across to me was that Obama wrote all of his speeches himself. Here’s the legal pad, take a look. I remember thinking, “Well, why would I think otherwise, until right now?”

I mean, of course Obama doesn’t write all his speeches himself. He’s the president of the United States; he’s got a team of seven White House employees who are paid to write speeches for him. But there was obviously a need or an instruction that had been given that Barack Obama was always to be presented as the author of Barack Obama. And by his instruction, the only book that the speechwriters were to consult was the Collected Speeches of Abraham Lincoln, because he was the only other president who deserved to be on the same shelf as Obama.

So the conclusion I’ve come to in time is that that best way to understand Barack Obama is that he is a literary creation of Barack Obama, the writer, who authored the novel of his own life and then proceeded to live out this fictional character that he created for himself on the page. Which is remarkable. So how do you write a biography of a fictional character authored by someone who’s deliberately created and obscured and erased their actual life and replaced that self with a fiction?

How do you write a biography of a fictional character authored by someone who’s deliberately created and obscured and erased their actual life, and replaced that self with a fiction?

The whole book’s really good, but the part that was most incredibly compelling to me is that period during which he transforms himself. Those chapters are fantastic and I think will be read forever because they’re as close to an explanation as anyone will ever have, I think, of the terrible, terrible, terrible isolation, the terrible, terrible loneliness, that the young Obama experienced before he reinvented himself as a fictional character in this incredibly American way.

Yes.

Which makes Obama almost the opposite of King, right? King, on a public level, had this incredible moral compass, had this incredible ability to connect empathy to the Bible, to politics, all in one flow of perception, and then mirror that back to people in ways that they recognized and that changed them. They were dealing with a remarkable and transformative leader who changed America.

Then there was the private Dr. King, who had affairs with multiple women and made off-color jokes and drank, and his behavior was hardly in any way a model or exemplary or what we consider moral behavior. Which, in a deeper historical sense, doesn’t matter one bit.

Right. The thing I wanted to highlight was that Doc, from birth up through college, lives in this loving cocoon of not just a family, but this wider community of Ebenezer and Auburn Avenue. He had the most privileged life a Black person could have in America in those years. The first time he really defies daddy is to leave to go to Crozer after he finishes Morehouse. So he’s never had a moment’s doubt about who is he, where is he from, who are his parents, who’s his family. It’s a cocoon.

The contrast to Barack could not be greater. He doesn’t know the daddy. He sort of knows the mother. He’s living with these elderly white people, and he’s being shuttled between Indonesia and Honolulu. And both in high school and at Oxy, and those three years in New York, his friendship network is all these guys like Chandoo Hasan, who are fellow international stateless children.

I think the pairing of King and Obama is an inevitable one for people in the present, at least, to make. Here’s the great civil rights leader who achieves this century-long dream of legal equality, and here’s the first Black-skinned president of the United States. Except, I can also make the argument that the pairing is fundamentally false.

Doc has no choice to be Black. Barack chooses to be Black.

MLK, the FBI, and the Press

You uncovered significant new information about the extent of Dr. King’s drinking problem and his womanizing, and even acts of violence against women, which seem to me to be a meaningful addition to what we know about one of the most important figures in American history. Yet, bizarrely, no newspaper or magazine in America would print your findings.

I mean, it was frustrating and bemusing—first with The Guardian, the New York Times Magazine, the Los Angeles Times. All sorts of people agreed to publish that and then went back on their word. Jodi Kantor at the Times was someone who tried to help me get that piece published. That’s why it got so much consideration at the Times, though the investigative people insisted it was a magazine issue.

I remember there was a female historian who condemned you for publicizing the details of Dr. King’s sex life, which seemed like a strange position for a historian to take.

The only people who were nasty about it were a trio of people whose professional history features a hatred of law enforcement. One of them had written a book about [the Black Panther and convicted murderer] Joanne Chesimard, or somebody like that.

You may have seen me say in print somewhere that there’s a very clear distinction in FBI documents. Something that comes from an electronic intercept is 99.9 percent reliable because they were very good transcriptionists. Where FBI records are bullshit is when it’s coming from human informants. Which is the whole elongated story of Dr. King being quoted as saying, “I am a Marxist.” Well, Morris Childs is telling the FBI what Gus Hall said Lem Harris told him that Stanley Levison told Lem. It’s like fifth-hand.

And the whole relationship between the bureau and the CPUSA was so totally fucked up because Hall and the other CPUSA hierarchy are embezzling significant amounts of money. The Childs were certainly embezzling some themselves. But the bureau is running the CPUSA. The bureau could have shut down CPUSA in about 1958.

Why did you say that the idea that Dr. King had been violent toward women changed your opinion of him? It has been known for a while that Dr. King, outside of the historical role he was called into, let’s say by God, was a flawed man who had issues with drinking and staying faithful to his wife.

Yes. Well, a garbled version of the same story is in my FBI book from 1981. There’d been two DOJ teams of lawyers, one run by a guy named Fred Folsom, and the other run by a guy named Bob Murphy, under Stan Pottinger, who had gone back through all that stuff and had listened to it. So several of the lawyers had told me this story about a woman being treated abusively, but they attached that memory to a story about a Las Vegas prostitute. So that’s what’s in my FBI book, and no one had ever particularly—

Oh, so it’s the same story, then?

It’s the same story, except it’s in Las Vegas with the prostitute, not the women from the Philadelphia Naval Yard at the Willard Hotel, which is the news story that was in the document dump, which I then wrote about.

The real crux of the problem with Doc was the binge drinking. But I’m very uncomfortable about emphasizing the drinking problem, because I fear that it sounds like you’re making some sort of fraternity-house excuse.

President Barack Obama jokes with Danish prime minister, Helle Thorning-Schmidt, left, as first lady Michelle Obama looks on at right during the memorial service for former South African president Nelson Mandela at the FNB Stadium in Soweto, South Africa, 2013
President Barack Obama jokes with Danish prime minister, Helle Thorning-Schmidt, left, as first lady Michelle Obama looks on at right during the memorial service for former South African president Nelson Mandela at the FNB Stadium in Soweto, South Africa, 2013

AP PHOTO/MATT DUNHAM

I doubt it happens very often that someone, especially a public figure, is sitting there stone-cold sober and decides, “Well, you know what would be a great idea? Why don’t I slap this woman across the face, in front of all these other people.”

I knew back in ‘85, ‘86, that by ‘67, ‘68, he had a drinking problem, because Marian Logan, a wonderful lady, described to me very powerfully, once when she was at 234 Sunset, Doc sitting on the bed drinking from a fifth of vodka, and Coretta seeing this and just not reacting. But that was Coretta’s MO: Don’t process things.

But I think I had assumed that it’s only when things sort of get so much tougher after ‘65 that the drinking really amped up. And, as with that memo from the state liquor agent detailing his interview with the Las Vegas prostitute, it was news to me that the drinking was out of control as of ‘64.

Also, I had been under the impression for years that in addition to Dorothy, there were maybe roughly 12 other women. What the NARA dump indicates is that if you count it all up, it’s about 40 to 45. And there’s clearly a compulsive quality to this.

But again, making the JFK comparison, even in terms of the Willard misbehavior—the woman who was like a White House intern, Mimi Beardsley Alford, whom [JFK] had service Dave Powers in the pool while he watched—there’s no getting around the fact that that was abusive.

Now the FBI is not honest with [Attorney General] Bobby [Kennedy] about that. They keep selling Bobby on Levison, Levison, Levison.

But it’s actually the women that they want.

Oh, yeah. Exactly. But I mean, at the same time, it is Doc’s fault that he’s promised the Kennedys he’ll stop working with Stan. Yet all they do is create Clarence [Jones, King’s lawyer] as an intermediary. And they’re not bright enough to realize that Clarence is tapped too. So it is understandable that RFK and the president think that King is not being honest with them.

On the other hand, neither Burke Marshall nor any of the other guys were told about the Childs brothers. So nobody in DOJ understood how good the FBI’s info was, because the FBI didn’t want to share it. The first person in the U.S. government who, outside the FBI, was ever shown the real importance of the Childs brothers was Senator Frank Church in the 1970s, because they show Frank a photo of Morris with Brezhnev and say, “This is our guy.”

Surveillance in the world of the ’60s was much simpler because it was so much smaller, and the technology was so much more labor-intensive. Running electronic surveillance in 1965 was really expensive and demanding. You had to do an installation, and even if you didn’t officially trespass in the installation, no matter where you’re doing it, it is difficult. And then you’ve got to get a leased line from the pole outside the house back to wherever. You’ve got to have a room. In Atlanta they rent this special apartment at Peachtree Towers. And then you’ve got to staff it 24/7. And with that tap on the SCLC office … I mean, the SCLC office has at least six telephone lines. The vast majority of what they’re getting on that tap is just secretaries talking to their boyfriends or people ordering pizza.

“I saw my proctologist today, and he said …”

And you’re getting stuff on folks’ kids. Most people who read this stuff don’t realize what electronic surveillance really means in terms of how much it picks up. They’ve never thought about it because they’ve never read the raw product.

But that product was rare, is the point that you’re making.

Oh, God. Yeah. Even at the height of Hoover, they’re not running more than 68 wiretaps in the entire effing country—a third of which are on foreign embassies, a third of which are on various mafia guys.

I was doing some research at the library in Maryland, the archives where Hoover’s papers are. I imagine most of the good stuff is located somewhere else, but the remaining contents of Hoover’s safe include letters from each U.S. attorney general, which obviously he made damn sure to procure, saying that they, as the attorney general, speaking for the president, had authorized him to conduct wiretaps. Hoover’s still sitting there in the ’50s and ’60s being like, “I’ve got to cover my ass with the letter from Tom Clark, because I know that the exercise of this kind of power is not sanctioned by the U.S. Constitution.”

Right. Exactly.

Whereas now this is a become a push-button feature of the software that these guys use. They can turn on your iPhone and have every word you speak transcribed by AI, under some phony third-hop FISA warrant rule.

The technology makes it so, so much easier. One of the landmark books, nobody remembers this now, was Jim Bamford’s first book on the NSA. Oh, my God.

So Obama starts out as an eloquent opponent of the Patriot Act, etc., etc. By the end of his presidency, his people are unmasking intercepts of his political opponents every day, and the FBI is spying on Donald Trump.

That’s right.

Where in the World Is Barack Obama?

What interests you most about Obama today?

The number one thing about Barack this past five years is how completely he’s vanished.

Why is he living in the center of Washington, D.C., then?

Well, how much time is he spending there as opposed to Martha’s Vineyard? I have no idea.

Between July Fourth and Labor Day, sure. The rest of the year, he lives in a large brick mansion in Kalorama. Doesn’t it strike you as weird that he’s an ex-president, he’s comparatively young, and he’s living in the center of Washington, D.C.? The original excuse was that Sasha had to finish school. Then you could say, “Well, the opposition to Trump needs a figure to rally around.” But now Sasha has graduated from USC, Trump is gone, Joe Biden was elected present, but he’s still there.

I never see any mentions of him.

Doesn’t that strike you as odd? I mean, I have heard from more than one source that there are regular meetings at Obama’s house in Kalorama involving top figures in the current White House, with Secret Service and cars outside. I don’t write about it because it’s not my lane. There are over a thousand reporters in Washington, and yet there are zero stakeouts of Obama’s mansion, if only to tell us who is coming and going. But he clearly has his oar in.

I don’t follow the Iranian stuff super, super carefully, but I have been puzzled at the Biden administration’s continuing attachment to the Iran deal.

The easy explanation, of course, is that Joe Biden is not running that part of his administration. Obama is. He doesn’t even have to pick up the phone because all of his people are already inside the White House. They hold the Iran file. Tony Blinken doesn’t.

Rob Malley was the guy on that.

Rob Malley is just one person. Brett McGurk. Dan Shapiro in Israel. Lisa Monaco in Justice. Susan Rice running domestic policy. It’s turtles all the way down. There are obviously large parts of White House policymaking that belong to Barack Obama because they’re staffed by his people, who worked for him and no doubt report back to him. Personnel is policy, as they say in Washington.

Which to me is a very odd and kind of spooky arrangement. Spooky, because it is happening outside the constitutional framework of the U.S. government, and yet somehow it’s been placed off the list of permitted subjects to report on. Which is a pretty good indicator of the extent to which the information we get, and public reactions to that information, is being successfully controlled. How and by whom remain open questions, the quick answer to which is that the American press has become a subset of partisan comms.

I’m going back to something you said 20 minutes ago. From the get-go, I know enough intelligence community stuff that from the first time I saw it, I realized that Christopher Steele’s shit was just complete crap. It was bad corporate intelligence, even. It was nonsensical.

What scared me back then was coming to understand that a new milieu had been created consisting of party operatives, the people in the FBI and the CIA who are carrying out White House policy, and the press. It is all one world now. And that’s something people still seem loathe to admit, even to themselves, in part because it puts them in a state of dissonance with this new kind of controlled consensus that the press maintains, which is obviously garbage. But if you question it, you’re some kind of nut.

As best I understand it, Glenn Simpson personifies that world.

He did five years ago. Now the question becomes, why are they still fixated on Iran after the Iran deal failed, its premises are exploded? And who are “they,” exactly?

Well, for Barack, everything has to be a success. Everything has to be a victory. I mean, I’m not a health policy expert by any stretch of the imagination, but I’ve always thought that the whole Obamacare thing was, in large part, a fraud. It’s a great achievement for the health insurance industry.

For Barack, everything has to be a success. Everything has to be a victory.

Obama reluctantly started talking about health care because it was Hillary Clinton’s issue in 2008, and then they were like, “Well, you have to have a healthcare plan, because Hillary has her big healthcare plan.” It was like, “All right, fine, I’ll have one too.”

I talked to the former Israeli prime minister, Ehud Barak, who was defense minister when the Iran deal was moving toward completion. And I asked him, “Well, what do you think is motivating this? “ And he said, “Well, Barack Obama’s not a normal politician. He is this strange combination of a college professor and a person who has ideas about his place in history. He decided that this deal was going to be the reason Barack Obama was going to be on Mount Rushmore. And that’s the reason that they could never let go.” I think he was right.

The irony is that the number one legacy of the Obama presidency is going to be the failure to intervene in Syria and the failure to object to Russia taking Crimea and the Donbas.

It’s interesting. I doubt that in the long run, Obama’s foreign-policy failures are going to be seen as the most important part of his legacy. I think future historians are going to look at the Obama presidency and see it as the moment when this new oligarchy merged with the Democratic Party and used the capacities of these new technologies and the power of this new class of people, the oligarchs and their servants, to create a new apparatus of social control. How far they can go with it, what the limits are … you see them trying to test it out every week or so.

So my question is: Is Barack Obama the author of this new machine? Did he create it purposefully? Does it report back to him? Or is it a larger phenomenon that originated partly on his watch, due to whatever combination of personal negligence and disengagement, and his sense that it benefited the Democratic Party or personally benefited him?

He has no interest in building the Democratic Party as an institution. I think that’s obvious. And I don’t think he had any truly deep, meaningful policy commitments other than the need to feel and to be perceived as victorious, as triumphant. I’ve sometimes said to people that I think Barack is actually just as insecure as Trump, but in ways that are not readily perceived by the vast majority of people. I think that’s probably my most basic takeaway.

But it does go back to Dreams being a work of fiction, that the absence of an actual personal story makes him need to compose one. For every time he says, “Oh, I spent years reading the history of the civil rights movement,” I know he read BTC, but I don’t think he read much else. This is someone who … 98 percent of his reading has always been fiction, not history.

Another thing I came away thinking after rereading your book was that I find Barack Obama deeply sympathetic as a person. I identify with him emotionally. Yet there was something about this fictional character that he created actually becoming president that helped precipitate the disaster that we are living through now.

For me, the crux of the issue is how Obama always refused to say the words “America is exceptional.” His famous answer was, “Well, I mean, every nation thinks it’s exceptional. So, yes, America’s exceptional in the same way Greece is exceptional.” What a funny thing for the American president to say. Exceptionalism is the main way that the country has always defined itself, and he’s just casually negated that because it annoys him that Americans make such silly claims. I think that dismissiveness was toxic, because nations, in the end, consist of shared symbols and myths. Debunking those myths, and saying the nation is bad, is a recipe for tribalism and fratricide.

I mean, I find him immensely likable and attractive, up through when he loses the congressional race in 2000. To me, there’s no question that the congressional loss creates, or deepens, or intensifies this hole that needs to be repaired, that needs to be filled. 

Michelle’s childhood is a South Side version of Dr. King’s. She knows who she is, she grows up in a close loving family and extended family, and then she ends up marrying a creature from another planet.

You were starting to touch on this earlier. Barack has the ability to identify himself as Black, not just for the vast majority of American white folks, but for the vast majority of American Black folks who have roots like Dr. King’s or Michelle’s. But both groups know that this is not a representative American Black person. It’s something else.

He is an administrator or guide from another planet who has come to bestow his genius upon these benighted people with whom he does not fundamentally identify.

He’s not someone who retains people. Even Valerie [Jarrett] and [David] Axelrod only go back to, like, 2003 with him. There’s no real history. The only person who’s a little bit of a through line is Rob Fisher, who I think is the brightest person I’ve ever met in my life. Rob would argue with him, and the second book, when Barack is trying to get the second book finished during the campaign, Audacity [The Audacity of Hope], Rob at one point tells him that it’s a mess. And Barack is angry. You can’t tell a U.S. senator that his book’s a mess. Rob would disagree with him in intellectual, academic ways, which had been a whole part of their closeness, and Rob put lots of time into Dreams—or into the earlier, right version of Dreams.

Now, Rob and his wife went to the White House a few times. I’ve got all the details on this because I remember Rob describing them to me sitting out on that Truman Balcony. But again, and this is not the usual sort of thing I say, but Barack doesn’t want to be close with people who are his equals. None of the people who are ostensibly his best friends are anywhere close to his equal.

I go back to the first chapter of your book, about these steel workers and all these mills closing down in Chicago and then Obama sort of deciding, “Well, we know here at the Joyce Foundation,” where he was then hanging out, “that nothing can be done to help these people. The solutions are on a national level.” At first I was, like, “Okay, whatever that means.”

But then it struck me in your telling that in fact, the place where he finds a home is not in community organizing. It’s in foundation-land, the place where foundations, foundation executives, very rich people, and politics meet. He was well spoken, Black yet white-coded, a credentialed academic, yet had some street cred because he’d been an organizer for that crucial year plus whatever, the way kids today start an NGO in order to get into Harvard.

So if Obama is the first U.S. president from the periphery of empire, he’s also the first president from the billionaire-foundation-NGO complex, which makes him the perfect mediating figure between the progressive part of the party, the billionaires, and the security state.

If one compares how he gets elected to the [Harvard] Law Review presidency and then how he functions as president of the Law Review to his U.S. presidency election and term in office, at the review, he’s seen as the least ideological figure.

And he’s perfectly comfortable with the incipient, sort of Federalist Society folks like Brad Berenson. And it’s a distant, light-touch management system. He has no investment in what the content of the volume ends up being. He doesn’t write his own note because he’s not that interested in producing a work of student legal scholarship.

Flipping way forward, those first three years in Springfield, he is a very serious state legislator. But once he has the congressional loss, then the purpose of being a state legislator is to rack up paper victories. To credential himself as a candidate. So, the Law Review presidency is like going to Harvard itself; it devolves to being a credentialing enterprise—just like what he’s doing in the state senate in, particularly, 2003, once the Dems take the majority. It’s now a credentialing process rather than an actual, personal investment in the policy substance.

But in the trends, in making himself a U.S. Senate candidate and then a presidential candidate, he loses both his interest in what had been modest but serious policy substance. And similarly, when he first gets to the Senate and he’s making that trip to Ukraine with [Indiana Sen.] Dick Lugar to look at decommissioned Soviet nuclear stuff, I think there is some actual interest and investment there. And Darfur, who the fuck is interested in Darfur? He was.

So, early on in his U.S. Senate time, I think it’s like an echo of Springfield. Some things are meaningful to him, but then he loses interest.

Roe, Affirmative Action, and the Court

You’re looking at the overturning of Roe v. Wade and affirmative action, all in a few months. So if this country’s politics underwent a sea change with the rise of wokeness, now we’re arguably witnessing a sea change or a correction in the opposite direction. Do you think that Martin Luther King Jr. would understand the Supreme Court ending affirmative action in higher education as a tragedy?

No. Doc did not buy into identity politics.

I have this long manuscript from a guy named Ernie Austin that he sent to me in, like, 1981. Ernie was the Appalachian coordinator for the Poor People’s Campaign. The white guy. No one remembers Ernie.

I think that as the scale or depth of affirmative action has gotten greater and greater, worse and worse, the beneficiaries are now so aware of being beneficiaries that it leads them to doubt themselves. And that’s doing harm.

As someone who has been a serious student of this subject for the past 45 years, how consequential is the court’s decision to overturn Roe?

It’s a class issue. That’s the number one thing. Even before Roe, if you were a woman who had your life together and could get yourself to New York, you were fine. If you had the time and the ability to buy yourself a plane ticket to New York City, you were fine. Anybody from the Rio Grande Valley needed to get, past tense, to San Antonio or Austin to get an abortion. And that’s what we’re looking at now, is that it’s a travel challenge, because there’s going to be this whole swath of states—Alabama, Mississippi, Georgia, Arkansas—where folks are going to need to get to New Mexico, Colorado, or Illinois.

Well, that’s certainly a greater geographical challenge than the one that women have previously faced.

Oh God, yes. But again, I mean, the problem with the reproductive rights movement, going all the way back to Mrs. Sanger in the teens and the ’20s, is that the activist population has no connection to the beneficiary population. Because the beneficiary population is generally poverty-class women who have messed-up lives—and, in some circumstances, abusive life situations. But they are working-class or poverty-class people for whom the ability to get out of Pittsburgh, just to use the local geography, to fly out of Pittsburgh, would be a humongous challenge for them. They can take the bus around Pittsburgh, but how do you get to the airport? How do you get a ticket? Where do you go? Do you have an internet connection at home?

And when one knows the clinical literature on abortion demography—and you see this dramatically in Mississippi or Arkansas, Louisiana, or Texas—the women who need abortions are not the women who have time to go protest. The women who need abortions come from, almost without exception, very deprived circumstances. And an unfortunate number of them are what clinicians call “repeaters.” People for whom it’s not the first abortion. That is the number one unspeakable issue on my side of this. And clinicians are very ambivalent about that.

And again, my side has never been forthrightly honest that there is a tremendous biological and emotional difference between a 10-week procedure and an 18-week procedure. There are plenty of clinicians who won’t go past 14 or 16 because it’s traumatic.

The pro-choice movement ought to be putting its resources into building and funding a travel network. I mean, don’t give to Planned Parenthood, give to the local organizations that support travel. Planned Parenthood has all these executives that are getting paid over half a million dollars a year.

Abortion is a weird issue for me. I don’t have any religious strictures about when a fetus becomes a human soul or any of that stuff. I frankly don’t understand Catholic strictures against birth control, except I guess in some kind of Norman Mailer existentialist, man-must-fuck-and-procreate-in-order-to-find-meaning kind of way. On the other hand, there’s something undeniably perverse about a political movement making a woman’s right to kill her fetus at any stage of development a flagship demand. Watching what happened in New York—where it became a matter for a woman and her doctor to decide whether to kill a baby as it was being delivered—it was hard not to feel that something had gone badly wrong on the pro-choice side too. Both the mother and the doctor should be put in prison because they are clearly dangerous to others. They committed murder.

Anyone who’s been a clinician, anyone who knows the clinical literature, who’s not somehow dramatically out of touch, knows that there is just a difference in kind between an 18-, 20-, and 22-week-old [fetus] and one under 12 weeks. I remember when Fran Kissling and Peter Singer organized this thing at Princeton in 2010, where both sides came to talk to each other. Fran Kissling’s been the best person on this for 30 years. I said that if there was going to be a solution on this, one side needed to agree that abortion up through 12 or 14 weeks was okay. And we needed to acknowledge that anything after 14 or 16 weeks had to require some meaningful standards. And, I said, it requires the other side to acknowledge that contraception is different in kind from abortion. And I got hissed.

But the underlying problem here is not unique to abortion. Whichever side is best able to cabin their crazies is going to come out ahead. Now, so far, the Republicans are losing that because their crazies, I think, are more visible.

Yet as totally pro-choice as I am, there’s no getting around the fact that Clarence Thomas, Neil Gorsuch, and Amy Barrett are intellectually superior justices to what the Supreme Court had in 1973.

Can you imagine Obama joining them on the court?

He’d be terrible because he’s too lazy. This is in the book. It goes back to him being Hawaiian. At one point, he says, “I’m fundamentally lazy and it’s because I’m from Hawaii.” That’s close to the actual quote.

Have you ever thought of writing a biography of Clarence Thomas?

Oh, yes. Yes. I have a huge collection of Thomas material.

I have to tell you that after meeting you and thinking about your oeuvre for the past few days, it seems like the natural capstone book for you to write. It will drive everyone on all sides nuts.

That would mean interviewing … oh God, all his former clerks. Oh God. The first piece I wrote about Thomas was a Times Week in Review piece in the Summer of ‘95, after Missouri v. Jenkins came down, explaining that Clarence Thomas is a Black nationalist. And I managed to get that in The New York Times. But that was 1995. Wouldn’t happen now.

Thomas has had a huge impact. And the network of former Clarence Thomas clerks. Oh my God. I mean, [the legal historian] Brad Snyder thinks that Felix Frankfurter generated an army of acolytes. Oh, wow. I mean, Thomas is at least as good.

It’s going to be interesting when someone like [legal historian] Brad Snyder puts Barack Obama and Clarence Thomas next to each other 50 years from now and asks his students, “Which of these two men had more of an impact on shaping the United States?”

Thomas is never going to get five votes to overturn everything going back to Palko. And he’s never gotten a second vote so far. Which shows that the vast majority of people writing about the court don’t know what the fuck they’re talking about. They don’t know what Chevron deference is, and they don’t understand that [former Justice Antonin] Scalia was, in large part, the father of Chevron deference, because he’s pro unrestrained executive power. And who have been two of the most pronounced critics of Chevron deference? Gorsuch and Kavanaugh.

I mean, the best legal news source is a one-man operation out of eastern Pennsylvania, run by a solo appellate litigator named Howard Bashman. It’s called How Appealing. And he just does it as a hobby; he’s done it as a hobby for 20-plus years. I bet 90 percent or more of federal judges look at it. But the quality of what’s published about the court now on Slate or Vox is just so awful.

Its party-line propaganda.

It’s just complete crap.

The Emperor and the Siege of Jerusalem

The Iran deal bothered you?

I do find the Iran deal offensive and puzzling, yes. I mean, it’s an explicitly antisemitic state.

It’s also a repressive theocracy that has consistently spread chaos and violence beyond its own borders. Yet the entire point of the Iran deal is that it’s a mechanism to allow us to bring this foreign and repugnant thing into the American global security system, to join ourselves to it. Why?

I also found the Cuba thing deeply puzzling and offensive. It’s a fucking dictatorship that imprisons all sorts of truly progressive, creative people.

Again, if you look at this as the revenge of the periphery of empire, these are the key symbolic issues of the periphery. Cuba, Iran. With a subtext of the Iran issue, of course, being diminishing and marginalizing Israel, because the Jews are so fucking annoying.

And, in that sense, there’s only little whispers of Obama’s feelings about Jews and Israel in your book, but those whispers show that you had your own thoughts about it. There’s the visit to the Spertus Institute for the Eichmann exhibit, where he has this big fight with Sheila because he won’t say that there’s anything bad about Steve Cokely, the Chicago alderman who at that time is accusing Jewish doctors of injecting Black babies with AIDS—Obama’s pose being that he’s too sophisticated, and at the same time too politically calculating, to see anything offensive about that. It’s just rhetoric, or an organizing tool, as he says later about Iranian Holocaust denial. You can see why Sheila gets upset.

Benjamin Netanyahu speaks to Barack Obama during a bilateral meeting at the Lotte New York Palace Hotel, 2016
Benjamin Netanyahu speaks to Barack Obama during a bilateral meeting at the Lotte New York Palace Hotel, 2016

Drew Angerer/Getty Images

Oh, God. Yes.

But historically speaking, Jews are not, or were not, a particularly American obsession, except among some morons and leather fetishists on the right. But they are a major obsession on the periphery of the American empire, where envy and fear of the mythic role that Jews supposedly play in Washington, because of Israel, are defining emotions, regardless of the facts.

So how do you talk all this foundation-land, community-organizer shit and then preside over the transformation of the country into a Gilded Age oligarchy? Maybe I just answered my own question: Obama is the Magic Negro of the billionaire industrial complex. And targeting Jews as outsiders and pushing them outside the circle was the way that the Gilded Age oligarchy consolidated itself in America, back then and also now.

Another thing we haven’t touched on at all, and I mean, I’ve certainly said this in the press any number of times in years past, but I’ve always found their need to hang out with celebrities bizarre. Because the people they both were, all the way up through at least 2000, would’ve had no desire to do that. It wouldn’t have crossed their minds to be with Beyoncé and Jay-Z or Richard Branson, or you name it.

Black people in Chicago, everyone, Jerry Wright, Hermene Hartman, they’re not surprised that Barack turned into someone else. But they can’t explain why Michelle turned into someone else. I think this is clear in the book. Michelle, for years, thought that all this talk about “I’m going to be president—”

Was nonsense.

Yeah. She listened to 13 years of that. And then, oh, my fucking God, it happened!

So maybe my husband is Jesus Christ, after all.

Then again, they’re all like that now. Think of the Clintons. The man from Hope. And Hillary, the great defender of children and the poor. And then its like, “Wait a minute. Did they just amass $3 billion in a private foundation, plus a private fortune of $300 or $400 million within three or four years after leaving the White House?” It’s not just the Obamas. The whole system is sick.

I did some research at the Truman Library recently for a screenplay I am writing, and on the way there you drive by Harry Truman’s old house, where he and his wife, Bess, sat on their porch after he was president. They went back there because that was their house.

I remember thinking, imagine telling Harry Truman, “Hey, why don’t you sell that old house and buy three or four huge mansions in Martha’s Vineyard and Hawaii and Washington, D.C., and rake in hundreds of millions of dollars in sweetheart deals with big corporations while you’re vacationing on rich people’s yachts?” He’d probably sock you in the jaw.

Allison [Davis, the head of the Chicago law firm that first employed Obama out of law school] said it to me, or maybe Allison said it to Jodi Kantor, that Barack once said to him that the only two things he wanted were a valet and an airplane.

Everybody, especially white folks, thought that having a Black family in the White House would be cure for the legacy of American racism. Now there’s no question in anybody’s mind that on that score, that scale, the presidency was a total failure. But why are race relations, at least as people perceive them or imagine them, ostensibly well worse today post-Floyd than they were in 2008?

It’s a great question. So many say, “Oh, well, Trump brought his white nationalism and his racism and his birtherism, and he divided people.” Which is true, except the point where race relations in America turned sour wasn’t with George Floyd in 2020; it was with BLM in 2014, and that’s squarely during Obama’s second term—well before anyone is thinking about Donald Trump coming anywhere near the White House. For 20 years before that, things had actually been better.

I think there was something corrosive about Obama’s public disengagement from the race issues that many voters, white and Black, looked to him to solve, or absolve them from. His answer was, don’t put that stuff on me. Put it back on you. Which, again, is a fine answerexcept for the fact that he was president of the United States.

I never paid much attention to birtherism for a large chunk of time, but I know I thought that they were making a mistake by not putting the actual birth certificate out there. And I think, in retrospect, there’s no question that it was horrific political malpractice not to put the birth certificate out there ASAP.

Why didn’t they?

Because Barack was so deeply contemptuous. It is comical; it is bizarrely comical to imagine he was born anywhere other than Kapi’olani Hospital.

Birtherism was a classic Trump move because it found a really quick way to encapsulate a feeling that people had, even if the facts weren’t true. The literal accusation—”Oh, he was born in Kenya, and his birth certificate is a fake”—was false, and it made Obama really mad. The word they kept using was racist. But I was like, “Did anyone ever suggest that Jesse Jackson or Lebron James was born anywhere besides the United States?” It was not about racism, I think—at least not primarily. It was about foreignness, un-American-ness. I think that what Obama feared was that showing the birth certificate would make his Hawaiian-Kenyan-Indonesian outsiderness even more plain.

The one time I met him, we talked about rap music at a fundraiser. The thing I was struck by, having spent a bunch of time in Bali, was the way he stood and the way he held his head while he listened. I recognized Indonesia in the tilt of the head and the stillness of his body. It was very familiar. Americans don’t have that kind of pose, or poise.

If we go back to ‘08, initially, there’s all that Black ambivalence about Barack as a presidential candidate, which, in his crude way, Jesse gives voice to. And certainly pre-South Carolina, I think there’s a lot of perception, as there was back in Chicago—I mean, Carol Harwell said this so well: “Barack’s not Black. Barack’s not from here. Barack hasn’t had the experiences my husband had growing up.”

So, I think it’s inescapable that Barack’s success in ‘08 is rooted in white people seeing him as an easy ticket toward racial absolution. It’s a need that white people in this country have. And what we’re still seeing week after week now for these past two or three years, especially with places like the Times and the Post, is that this white need for absolution was not cured by the Obama presidency. I frankly don’t understand it.

I think that it’s culturally and intellectually part of the New England DNA, which Obama—the president of the Harvard Law Review—taps into. To me, the most profound thing that was ever written about the New England Puritans was written by Perry Miller, whose thesis was that the Puritans go to New England with the goal of redeeming old Europe by building a shining city on a hill whose example will put an end to all the wars in Europe. Except, of course, the example of the New England colonies has no impact on Europe whatsoever. Nobody in Prague or Vienna gives a shit about Narragansett.

At which point, the Puritans have to explain why this great vision that they have sacrificed for and died for, having essentially traveled off the map of the civilized world and gone to the 17th-century equivalent of Mars, didn’t quite go as planned. And at that point, you have the American turn into self-absorption and narcissism. The fault is in us, you see. We must turn inwards and scour our souls for sin, because God is punishing us. And this is the link between both the deep narcissism and the redemptive impulse of New Englanders, which I think has been a constant in that region and in its impact on American history ever since.

But we still have, in the present-day world, we have these millions of white folks who are still actively seeking absolution. And I presume that has to be grounded in an inner fear of asking themselves, “Am I unconsciously racist?” That’s never been a part of me.

The protagonists of the grand drama of race in America are the cultural and actual descendants of the Puritans, not Black people—who, as Americans, mainly desire the same things that other Americans do, like safe streets and decent jobs and health care and not to die prematurely from heart disease. White Puritans have more elevated concerns.

Exactly. For them, 200-year-old statues are more important than five-year-old Black children.

I want to go back to something about Barack I’ve mentioned twice now. Barack never had any loyalty toward any of these people. Use John Kennedy as an example. I mean, whatever else we say about Kennedy, he remained intensely loyal to people who went back way before the presidency with him. Kenny O’Donnell, for example. Lem Billings was openly gay at a moment when that was hardly fashionable or acceptable. They all loved and accepted him, quite publicly, because he was Jack’s best friend from prep school, and that continued after Jack was dead. Friendship was everything to them.

That’s because the Kennedys are from somewhere. Their communal and religious ties were real and organic, not some product of some abstract progressive ideology. Honey Fitz was the mayor of Boston. They all went to church every Sunday, or else Rose would beat them.

What do the Obamas and their circle have in common with each other? They are Ivy League people, who ran away from whatever they came from in order to become members of the credentialed elites, whose loyalty is to the system that gives them prestige—or rather, gives prestige to their degrees, of which they are the holders. Once they pair off and reproduce under the seal of Harvard or Yale, they may find it seemly to donate money to an NGO that offers microloans to female entrepreneurs in Pakistan. So why should Obama, the ultimate winner, carry on the charade that he’s part of a community, whatever that means, with these people? He’s happy to go on NPR and talk about meaning or Marilynne Robinson novels or whatever, to make the wine moms identify with him, so he can put one over on them. Just don’t ask him to visit the hospital when you get cancer, because he’ll be hanging out on someone’s yacht, with the other winners.

But in Springfield, there’s a real community of Illinois politicos. There’s a guy named Matt Jones who was very helpful to Barack, who in fact came down with some incredibly rare cancer about two, three years ago. And the person who was the centerpiece of this was a guy who was a Senate judiciary staffer named Pete Baroni, a really wonderful man. So, Pete organized some crowdfunding thing for Matt. And so, you could see everybody in Springfield, Democratic and Republican, had donated to Matt Jones.

And then very early on in COVID, about six, eight weeks into COVID, the woman who was finance director on Barack’s Senate primary run, Claire Serdiuk, up and died at age 50, leaving behind a 4-year-old. And when I went to the GoFundMe page for Claire, you could see everybody who’d worked on the Obama primary campaign, and then Claire went to SEIU [Service Employees International Union], and the folks at SEIU all donated. Anybody whom I’ve interviewed in that situation, I would donate to, always have.

But Barack has no interest in any of that. It’s just not there.

It’s like your question “Why is he at an event with Jay and Bey? Why does he want a private plane?” And the answer is, well, because those are the things that winners get.

But you remain hollow.

They’re all hollow. That’s what the system produces.

David Samuels is the editor of County Highway, a new American magazine in the form of a 19th-century newspaper. He is Tablet’s literary editor.

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