Jerusalem. (Jordan Sitkin/Flickr)

When Philip Weiss, the Jewish anti-Zionist writer and blogger, compares himself to Theodor Herzl, he’s not being ironic. “I actually am like him in certain ways,” he says. “Herzl said, ‘Anti-Semites made me Jewish again.’ I would say that neo-conservatives made me Jewish again.”

To the legion of Jews that Weiss has enraged, this will sound perverse. It’s certainly self-aggrandizing. But it also gets at the way that Weiss has abandoned a deeply assimilated life for a profound—if idiosyncratic and tortured—engagement with Jewish questions. As the founder of Mondoweiss, a blog that has become a nucleus of anti-Zionist writing, and a co-editor of a new book about Richard Goldstone’s report on Israel’s 2008 invasion of Gaza, Weiss says that he now thinks about Jewishness all the time. In his fierce critique of tribal identity, he’s found his tribe—one he believes is growing.

“I think I was alienated from a lot of Jewish communal life in my 20s, 30s, 40s,” Weiss says. “One symptom of that is the fact that I’d never been to Israel until 2006. I was 50 before I got to Israel.” Now that he is 55, Israel has become the center of his life. He goes to rabbinical conventions and corresponds with left-wing Israelis. “I love what I’ve undergone in the last few years,” he says. “And I love my engagement with Jewish communal life now.”

Of course, much of that engagement comes in the form of relentless criticism. Weiss’ blog is fulsomely, intensely anti-Israel—it’s a universe in which even Noam Chomsky, hero of anti-imperialists worldwide, is criticized for his residual attachment to the Jewish state. His obsessive focus on Israel has come at the expense of a successful career as a magazine journalist. Harvard-educated, he got his start writing for the New Republic and later contributed features to New York, and the New York Times Magazine and wrote a column for the New York Observer. Initially he launched Mondoweiss as a general-interest blog on the New York Observer website. When he started to focus on Israel, his editor warned him that he was becoming a crank.

He didn’t listen, and in 2007 he left the Observer, taking the blog with him. Today it operates under the umbrella of the nonprofit Nation Institute, which allows Weiss to solicit tax-deductable contributions. But its budget comes entirely from donations, and Weiss has to rely on his wife, the writer and editor Cynthia Kling, to help support him.

It’s a little hard to figure out why Weiss threw so much away for a cause that was so new to him. Naturally, he sees a linear moral logic to his journey. He looks at contemporary Israel and is appalled. Because he came to Middle Eastern issues late in life, he has no fond memories of labor Zionism, or maddening recollections of the times Palestinians spurned opportunities for peace, to complicate his anger. As one long alienated from Jewish life, he hasn’t developed the habit, common to many American Jews, of reflexively giving Israel the benefit of the doubt. For him—as it is for many younger Jews—Israel is defined by Avigdor Lieberman and Operation Cast Lead, by Shas and settlements.

Weiss first became interested in Israel in the run-up to the Iraq war. “I felt there was some element of Jewish organizational life that was behind this war because it was good for Israel,” he says. The notion that the neoconservatives spoke for American Jews horrified him, and it imbued him with a sense of responsibility to speak out as a Jew. As he dove into books about Jewish and Middle Eastern history, he came up against what he saw as the essential conflict between Zionism and American liberalism—which, after all, defines itself precisely by its refusal to privilege any race or religion. Liberal Zionists are used to holding these ideas in uneasy tension. Weiss could see nothing but stark dissonance. “I don’t believe in the necessity of a Jewish state,” he says. “Most Jews disagree with me, and that is sort of the heart of my crisis.”

The idea that American Jews might someday find themselves persecuted and in need of refuge strikes him as paranoia. “Temperamentally, I lack a paranoid gene,” he says. He grew up, he adds, hearing that Jews would always and everywhere be in danger. “And my whole experience has been the opposite.”

That still doesn’t quite explain why he jettisoned so much to devote himself to anti-Zionism. But there’s something in Weiss that reacts intensely to disillusionment. Once he rejects conventional wisdom, he’s willing to swing wildly, even heedlessly, in the other direction. In the 1990s, he was a staunch Bill Clinton defender. But when Clinton disappointed him, he began a long flirtation with all sorts of anti-Clinton conspiracy theories. His New York Observer columns painted an image of a menacing cabal of thugs sitting in the White House and snuffing out their enemies. As he wrote in 1998, “Everywhere Bill Clinton goes, he makes Chinatowns.” He was particularly fixated on Vince Foster’s suicide, which he was convinced was part of something larger and more sinister. He has more of a paranoid gene than he realizes.

He regrets some of this now. “I have problems with loyalty in life, and I felt little loyalty to the Democrats when I sensed the small-town corruption that hung around Clinton,” he wrote in 2009. “I wanted to expose it. It was the wrong impulse because as John Homans, my friend/editor, used to berate me, You’re arming people who disagree with you on policy matters. Did I help elevate W? … And would Gore have kept us out of Iraq? Maybe. That’s why I feel bad about what I did.”

Friends have suggested that the same impulse that sent him after Clinton may drive some of his writing about Israel. Though his voice can be reflective, he seems to enjoy pulling wild ideas from the fever swamps and giving them a respectful airing. He’s particularly interested in Jewish power, manifestations of which he diligently catalogs.

“Over and over, American presidents have said they oppose the colonization program; over and over these instincts have been nullified politically because of the Jewish presence in the power structure,” he wrote in 2009. “The Senate is dominated by Democrats, and 1/5 of them are Jews, even though Jews are just 2 percent of the population. The Washington Post has said that over half the money given to the Democratic Party comes from Jews. Obama’s top two political advisers are Jewish, Rahm Emanuel and David Axelrod. The news lately has been dominated by Obama aides Kenneth Feinberg and Larry Summers. And what does it mean that the Treasury Sec’y gets off the phone with Obama to confer immediately with Lloyd Blankfein of Goldman and Jamie Dimon of Morgan (Dimon’s Jewish; Blankfein would seem to be)?” He didn’t say what exactly this did mean, particularly regarding Israel—it was just an invitation to conspiratorial speculation. From there, Weiss went on to list Jewish journalists including Ezra Klein, Andrew Ross Sorkin, Terry Gross, and Nina Totenberg.

Now, it’s fair for Weiss to argue that Jews, owing to their success, are far more secure in the United States than they realize, and that their politics should reflect that, just as it’s more than fair to criticize the pro-Israel establishment for its destructive impact on American foreign policy. What’s outrageous is the imputation of a unified Jewish agenda to all these disparate figures, most of whom have nothing to do with Barack Obama’s Middle Eastern policy, and some of whom are far to the left of virtually all non-Jewish Republicans on Israel issues. Netanyahu has reportedly slurred Emanuel and Axelrod as self-hating Jews; there’s certainly no evidence that they’ve urged softness on settlements.

Not surprisingly, some Jew-haters see Weiss as a native informer, telling the plain truth about the Zionist octopus. “Philip Weiss is a unique American Jewish voice—a Jew without all the usual rationalizations and blind spots–at least most of them,” Kevin MacDonald, a leading anti-Semitic theorist, wrote last May. MacDonald has bandied the idea of taxes on Jews and quotas against them in order to “achieve parity between Jews and other ethnic groups.”

Weiss isn’t responsible for his fans, of course. But when he wrote about McDonald’s embrace, there was something notably equivocal in his rejection of a figure who most American journalists and thinkers would find beneath contempt. “I find a lot of what MacDonald has said elsewhere bracing and bold,” he wrote. “He is alive to important sociological trends that few people are talking about out loud.” Only then did he call him out for his open racism and disdain for Jewish suffering.

Yet Weiss can’t simply be written off as a victim of self-loathing. His ambivalence toward the Jewish world is too complicated, suffused with attraction as well as lacerating anger. When he first went to Israel, he says, he was surprised by his satisfaction at seeing Jews with guns. He was moved by the silence in West Jerusalem on the Sabbath, and by the struggles of young Israeli leftists like those who’ve clustered around the +972 blog. “I am ethnocentric,” he says. “And as much as I’m involved in Palestinian solidarity, I emotionally look to other Jews.”

“I find his writing about Israel to be infused with a real Jewish concern,” says J.J. Goldberg, former editor of The Forward and a friendly acquaintance of Weiss’. “Some people who are associated with him write about Israeli wrongdoing with what seems like glee. He seems to have regret.”

Lately, Weiss is particularly gratified to see a growing number of Jews moving in his direction. “I think there’s going to be a big anti-Zionist moment in American Jewish life,” says Weiss. “I just think it’s inevitable.”

He may be right. Take Lizzy Ratner, for example. One of Weiss’ co-editors on the Goldstone book, Ratner is a former New York Observer writer who was born into New York’s elite Jewish establishment—her father is millionaire real-estate developer Bruce Ratner. Lizzy was 4 years old the first time she went to Israel; during college she spent a semester there and was at the rally when Yitzhak Rabin was assassinated. Her horror led her to get involved in pro-Palestinian work.

“The moment I crossed a checkpoint, 15 minutes from Jerusalem, the world changed,” she told me. “My worldview shattered. You grow up being told ‘they’ want to push us into the sea and we have to do everything we can to stop this evil enemy that wants to kill us and is going to kill us, and then you meet the terrible evil enemy, and not only are they nice, and decent, but they’re actually oppressed.”

Returning from Israel in the 1990s, Ratner looked for a community of people who shared her concerns with the Middle East, and she couldn’t find it. She’d go to Palestinian solidarity meetings, and only three others would show up. Gradually, she drifted away from the issue altogether, until outrage over Gaza inspired her to get involved again. She found a movement to plug into. “Now I look at Phil and Adam’s website”—Adam Horowitz has been Weiss’ partner at Mondoweiss since 2008—“and I look at Jewish Voice for Peace—something undeniable is welling up,” she says.

Meanwhile, as Weiss has become more enmeshed in the world of left-wing anti-Zionist Jews, he’s become at least a little more sensitive to Jewish concerns. “I know I’ve made a lot of mistakes on my site over the years,” he says. “I think in my alienation from the Jewish community, I said stuff that I regret on a number of occasions.” He even has second thoughts about some of more strident attacks on neoconservatives. “The neoconservative thing is a very confusing thing to me,” he says. “I think it’s appropriate to talk about Jewish neoconservatives, but there’s an element of red-baiting. I haven’t come down fully on that issue. I know I’ve hurt people.”

And so his alienation from the Jewish community has been transformed into a new sense of mission within it. “There’s a crisis! There is truly a crisis in the two-state solution,” he says. “That de-marginalizes me.” He’s right, whether that fills you with hope or with dread.