Four years ago, then-Sen. Barack Obama embarked on a whistle-stop tour that included stops in Baghdad, Kabul, Amman, Jerusalem, Berlin, and London. It wasn’t the first quasi-diplomatic mission by an aspiring leader of the free world—Ronald Reagan, for one, traveled to Tehran in 1978 in anticipation of the 1980 campaign—but Obama’s trip created a new template for candidates wishing to project authority and gravitas in the foreign-policy arena. Obama, of course, had spent considerable time living abroad as a child, but the trip showcased him doing the kinds of things the American people like to imagine presidents can credibly do, like playing basketball with grinning soldiers in Baghdad or electrifying a capacity crowd from an outdoor podium in Berlin. In Israel, a country he had already visited once as a sitting senator, Obama had another objective: putting to rest the persistent notion, prevalent among Florida voters, that he didn’t have sufficient feeling for the Jewish state in his kishkes. Hence the indelible image of the senator standing in front of a bank of spent rocket casings, brandishing a T-shirt emblazoned “I ♥ Sderot.”The goal for former Massachusetts Gov. Mitt Romney, when he lands in Jerusalem this weekend, is precisely the opposite. Rather than showing how much he really, really likes Israelis, the presumptive Republican nominee is going to the Promised Land to give its Jews the opportunity to demonstrate how much they really, really like him. Romney will engage in meetings with leaders from across Israel’s political spectrum and hold a $50,000-a-head fundraiser for visiting and expat Americans at the King David Hotel in Jerusalem. But the visual highlight of the trip will come Sunday night, when Romney is scheduled to join Prime Minister Benjamin Netanyahu in breaking the ritual fast of Tisha b’Av, a holiday commemorating the destruction of the First and Second Temples that lends itself to assertions of modern Zionist pride. The point, plainly, is to advertise Romney’s ability to elicit from Netanyahu a degree of personal warmth that has eluded the president through his first term—the kind of spontaneous, unstudied closeness last seen between the legendary chaverim Bill Clinton and Yitzhak Rabin.Romney’s visit is the brainchild of two other men: Ron Dermer, the American-born political operative who is Netanyahu’s chief strategist and speechwriter and, more importantly, Dan Senor, a Republican politico-turned-investor who is a close adviser to the Romney campaign. Senor—who is famous in pro-Israel circles as the author of the best-selling 2009 book Start-Up Nation—has taken Romney to Israel twice before, once in 2007, before the governor’s first presidential bid, and again last year. This spring, he accompanied New Jersey Gov. Chris Christie, a Republican who has endorsed Romney, to the prime minister’s office in Givat Ram to meet with Netanyahu and Dermer. But the current trip, coming so late in the campaign season, was planned quietly, for fear of provoking a possible last-minute visit by President Obama, who has been criticized by some Jewish groups for failing to return to Jerusalem since his inauguration. Late last month, while Senor was in Jerusalem for his niece’s bat mitzvah, he met Dermer for breakfast at the King David Hotel; a few days later, with the Romney campaign’s blessing, Dermer gave the scoop to the New York Times.To some, Senor remains best known as the spokesman for the Coalition Provisional Authority, a role that made him a regular television fixture in the immediate aftermath of the 2003 Iraq invasion. In the years since, he’s reinvented himself as a cable news commentator and Israel advocate and has simultaneously amassed his own fortune working on Wall Street. He is, even among people who vehemently disagree with his politics, a popular guy who moves with equal ease in New York and Washington. He arrived in the governor’s camp with his own celebrity, and, in a sense, he offers the socially awkward candidate the thing his campaign most craves: an easy ability to make people like him. More importantly, Senor has been a vital emissary over the past six years for Romney not just to the Israelis and the American Jewish community, but to a Republican foreign-policy establishment that, even today, remains somewhat alien territory.“Dan was hugely helpful in introducing the governor to his friends and colleagues,” said Beth Myers, Romney’s longtime aide-de-camp and a top campaign adviser. “He’s a huge validator.”***Senor arrived at his current role by way of an itinerant and mostly accidental career that has afforded him access to a wide range of very powerful, very famous, and very rich people. As an ambitious college intern on the Hill, he caught the attention of William Kristol, the editor-in-chief of the Weekly Standard, who gave him entree into the neoconservative circle surrounding George W. Bush. Senor eventually became the face of the Bush Administration’s efforts in Iraq, both during his time in Baghdad and later as a television pundit; while he was in Baghdad, he met his future wife, Campbell Brown, then a reporter for NBC. In between he went to Harvard Business School, worked for the Carlyle Group, and started a private-equity firm with his classmate and friend Chris Heinz, stepson of former Democratic presidential candidate Sen. John Kerry.But his greatest success came in 2009, with the publication of Start-Up Nation, a slim blue-and-white volume he wrote with his brother-in-law, the Israeli newspaper columnist Saul Singer. Since its release in 2009, at the depths of the financial crisis, the book has become required reading for the entire Israeli government and for much of the American Jewish community. (The Palestinian Prime Minister Salam Fayyad also keeps a copy on his desk.) The title alone has become shorthand for the modern, techno-centric aspects of Israel, as distinct from the Israeli-Palestinian conflict. “It showed that every conversation about Israel doesn’t have to be about the settlements,” Senor told me when he and I met recently for dinner at Solo, a kosher restaurant in Manhattan.In 2010, Senor was floated by Republicans, including Rudy Giuliani, as a possible Senate candidate in New York, but he decided not to enter the race, which would have pitted him against popular Democratic Sen. Kirsten Gillibrand. He now works for Paul Singer, the billionaire hedge-fund manager who is among Romney’s most prominent Wall Street backers. (Singer is no relation to Senor’s brother-in-law.) Senor is also a regular on Morning Joe, where he has become the show’s go-to conservative guest. To critics on both the left and the right, he represents the worst of the Bush era—the prioritization of loyalty and ideology over experience and expertise. “He was on MSNBC pushing for more robust intervention in Syria, and he was going up against a general,” said one longtime Republican operative, who asked not to be identified. “I was saying to myself, This is a guy where, if you look at him, no one’s ever going to confuse him with anyone who ever put on a uniform.”But Senor’s varied background makes him a perfect interlocutor for Romney in clubby think-tank and fundraising circles. “There are a lot of smart guys in Washington who do some policy, some politics, some fundraising,” Kristol said. “But he certainly knows more than a lot of those guys, or knows better how it works.” In September 2009, after Romney’s first run for the Republican nomination, he joined Senor onstage at a conference hosted by the Foreign Policy Initiative, an organization Senor launched with Kristol and Robert Kagan. Romney made passing reference to an op-ed in the Wall Street Journal, prompting Senor to note it had been written by Bret Stephens, a columnist well known in conservative circles. “Brad Stephens’ piece?” Romney asked, blankly. “Bret Stephens,” Senor corrected. “Bret Stephens,” Romney repeated, and looked out at the audience. “Sorry, Bret.”But, in a year when Israel has emerged as a central foreign-policy litmus test, Senor also brings an unusual advantage to the governor’s campaign: his close relationships with a small, influential group of American expats clustered in Jerusalem’s German Colony who operate at the highest levels of Israeli public life. Much has been made of Romney’s pre-political acquaintance with Netanyahu, dating to when they were both young men working for the Boston Consulting Group. But Senor, who travels to Israel several times a year, has ties to Jerusalem’s elite that are unusually personal and that are magnified by the uniquely Anglo-inflected nature of Netanyahu’s current government.Continue reading: The magicianThere is Dermer, whom Senor emails with and speaks to regularly. Senor’s sister Wendy, a former Democratic congressional staffer who heads the Jerusalem office of the American Israel Public Affairs Committee, has the ear, and the direct phone number, of just about everyone in the Israeli government. Saul Singer, Wendy’s husband, is a former Republican congressional staffer and a longtime columnist for the Jerusalem Post who is now a fellow at the Israel Democracy Institute. (Singer is also the older brother of Alex Singer, whose death in IDF service has been memorialized by their parents, Max and Suzanne, in the book Building a Life.) They are, in turn, friendly with Michael Oren, the American-born historian who now serves as Netanyahu’s ambassador to Washington. “This is a group that speaks American and, to a large extent, understands Israeli,” said Yossi Klein Halevi, a writer and fellow at the Shalom Hartman Institute.Ironically, Senor has had more success than any of them at translating Israel’s own image of itself for an international audience. “There’s really been a Pygmalion effect,” said Tal Keinan, a business-school classmate of Senor’s who now runs an asset-management firm in Tel Aviv. It’s also changed how outsiders reflect their enthusiasm for the country: Just last month, Google chairman Eric Schmidt used the “start-up nation” phrase in a meeting with Netanyahu. Romney has, unsurprisingly, been equally receptive. “Anything related to the economy is a way to capture his energy,” Senor told me. He described taking Romney, on a previous trip, to meet Israeli entrepreneurs and venture capitalists. “He could have stayed all night, to the point where the next day he told me if he’d still been at Bain which ones he’d have soft-circled.”***Senor has a remarkable talent for cultivating mentors. Beginning with Kristol, who is almost two decades his elder, Senor has flourished under the watch of a succession of father figures, including former Republican Sen. Spencer Abraham of Michigan, a founder of the conservative Federalist Society, and David Rubenstein, the head of the Carlyle Group (and a Democrat). And, now, Mitt Romney. “I’ve never met anyone who successful, older men want to mentor or sponsor more,” Chris Heinz told me.Senor’s own father, Jim, died of a heart attack the Tuesday before his son’s bar mitzvah. He was 62. “The rabbis said we could pick another date, you know, no pressure,” Senor said. “But he’d practiced with me—he knew it better than I did—and it weirdly felt therapeutic to do it. I felt like he’d be there with me, and if I picked another portion that he didn’t know, he wouldn’t.” Senor paused. “Just to know that’s the portion I delivered, even though he wasn’t there, was important,” he added.His three older sisters were already grown—Wendy, the next youngest, is eight years his senior—leaving him and his mother, Helen, a Holocaust survivor from Kosice, now part of Slovakia, alone in Toronto, where Jim Senor had moved the family from upstate New York in the early 1970s, to take a job with the Canadian branch of Israel Bonds. They considered moving to Cleveland, where Jim had grown up, but ultimately decided to stay put. “My mother felt like she’d been on the run her entire life, and she really had been,” said Senor. As a girl, his mother and grandmother went into hiding after the Nazis rounded up the city’s Jews, including Senor’s grandfather, who was deported to his death at Auschwitz. After the war, they fled west from the Soviets, arriving first in Paris and then in New York before making their way to join family members living in Montreal.Senor told the terrible story of his mother’s lost youth vividly, miming his grandmother hiding under a sheet to light Shabbat candles. The experience, he said, made her leery of public Jewish displays like a United Jewish Appeal-sponsored fundraising walk-a-thon through Toronto’s downtown neighborhoods. “They shouldn’t do that, they’re drawing too much attention,” Senor remembered his mother worrying. “So, that’s her world,” he went on, “the Holocaust experience, which was very heavy for us growing up.”After his father’s death, magic—an archetypal province of smart, lonely boys—gave him an outlet. As a teenager, he’d stop on his way home from school at a store called Browser’s Den of Magic, where he pestered the staff to teach him tricks. Eventually, with another friend named Dan, Senor started a business, “Dan and Dan the Magic Duo,” and paid his way through high school and college, at the University of Western Ontario, playing bar mitzvahs and weddings. He kept it up and eventually used it to endear himself as a young staffer on Abraham’s 1994 Senate campaign and then in his Washington office. (Senor, on Kristol’s advice, chose to work for Abraham over another young up-and-coming Senate candidate, Rick Santorum.) “Among the many requirements over the years in terms of his relationship with the Abrahams was that when each of my kids turned 6, he did a full dress appearance at our house,” said Abraham, who went on to become energy secretary in George W. Bush’s first term. “He had the full black cape, the whole outfit.”By the time Senor met Abraham, he’d made the shift from the reflexive Democratic stance he was raised with to full-blown conservatism. His first job in Washington, as a high-school student, was with Rep. Ed Feighan, a Democrat from Ohio who was on the Foreign Affairs Committee, who had him write letters about funding for the Contras. “On these foreign-policy issues, having to research these things and write these arguments I totally disagreed with, I started to be drawn to the Reagan peace-through-strength idea,” Senor told me over dinner. The next summer, with help from his brother-in-law Singer, Senor got a job working for Sen. Connie Mack, the Florida Republican, and the summer after that, he interned at AIPAC.After graduating from Western Ontario with a degree in history, Senor decided to go study at Hebrew University. He was in Jerusalem during the 1993 Likud primary and volunteered as a student intern not for Netanyahu, who won the race, but for Benny Begin, son of Menachem Begin. “I still have my Benny Begin for Prime Minister T-shirt,” Senor said. After Begin’s loss, he began doing research for Tom Hundley, a Chicago Tribune reporter who met Senor when he accompanied a group of Hebrew University students to Poland on a March of the Living tour. The tour had caused controversy on campus after administrators tried to block students from going in the midst of a national political debate about how to teach younger Israelis about the Holocaust; Senor joined a group of students agitating to miss classes in order to go. “If it takes sending 1,200 kids to look at graves in Poland to make us Zionists,” Senor was quoted in a story Hundley wrote about the trip, “it means they are doing something wrong in Israel.”***There is an argument to be made that, had things gone differently in Iraq, Senor would never have been as successful as he is today. He had no plans to join the Bush Administration after graduating in the spring of 2001 from Harvard, where he was chosen as a commencement speaker. He had missed the 2000 campaign and had accepted an offer from the Carlyle Group, where he was set to start work in October. But after the Sept. 11 attacks, Senor watched his Washington friends gearing up for the Iraq war and in March 2003 signed up for a posting in Qatar, where the Pentagon was establishing a media center ahead of the American-led ground invasion.Continue reading: Iraq and afterSenor was originally supposed to stay for 90 days and then return to a White House job in Washington. Instead, after the initial phase of the war was over, he was sent to Baghdad and wound up working for Paul Bremer, the chief administrator of the Coalition Provisional Authority, as spokesman. Senor was an unlikely person to deploy to a war zone. For one thing, he keeps kosher. “He had more cans of tuna than anyone I knew,” said Mark Kimmitt, the general who served alongside Senor as military spokesman in Baghdad. “Anytime any of us thought we had a fever we’d grab him, because he had so much mercury in his blood.” (He’s also a picky eater; when we met, he ordered a hamburger with no onions and mustard and mayonnaise on the side, in the precise manner of Meg Ryan’s When Harry Met Sally character.)But he also had relatively limited Middle East experience, aside from having spent time studying in Israel—not necessarily a plus when dealing with Iraqis—and spoke no Arabic, a common limitation among the young, smart set working for the Coalition Provisional Authority. People who interacted with Senor in various professional capacities said he was no less prepared than others, and several people who clashed with him in Baghdad pointed out that he had the advantage of being pleasant to deal with. Bremer, who describes himself as a fan, credited Senor for pushing him to start appearing on Iraqi television. “He was everywhere, and he was an energetic guy,” Bremer told me. And, in some ways, it gave Senor a breadth of field that would have been difficult to match in Washington. “There are really very few people who have that ability to see politics, policy, and media, but Iraq is really what developed him in all three directions at once,” said Elliott Abrams, a senior fellow at the Council on Foreign Relations who was then on the National Security Council staff.Senor had total faith in the Iraq enterprise. “I did believe the reaction to 9/11 could not just be a military one,” he told me. “It can’t just be whack-a-mole, you know, go find al-Qaida with the Taliban in Afghanistan. The only shot we had at reshaping the battlefield, metaphorically speaking, the battlefield that was producing people climbing into airplanes and blowing them up in the U.S., was to try to reform some parts of the Arab world.” And he genuinely believed that Saddam Hussein had weapons of mass destruction. “I had to do 8,000 different shots, inoculations against this chemical attack and that one,” Senor told me.As the postwar environment deteriorated through the fall of 2003, Senor continued to do his job spinning the bad news, even as it took him to greater heights of truth-stretching. To his critics among the press corps and among opponents of the war, he was simply lying to save face for the administration. His most infamous quote, reported by the Washington Post’s Rajiv Chandrasekaran in his book Imperial Life in the Emerald City, was: “Off the record, Paris is burning. On the record, security and stability are returning to Iraq.” In Senor’s mind he was doing the best he could in very bad circumstances. But he wasn’t making friends back in Washington, either. He vividly recalled getting a phone call from a senior White House official in November 2003, when Iraqi representatives boycotted a live press conference he had arranged to celebrate an interim constitutional agreement. “I’ll never forget,” he said. “They were flipping out, because they’re sitting in the West Wing watching this and saying, ‘Do you realize what a disaster this is?’ ”“I can’t think of anyone who Mitt has ever met that he hit it off with so immediately as Dan Senor.”By the time he returned to the United States in 2004, Senor was near-toxic. (Bremer wound up retiring to Vermont to become a landscape painter.) He took a paid gig as a commentator for Fox and wound up back in New York, where he pursued his romance with Brown and started his business, Rosemont Capital, with Heinz. In the end, it paid off. “The real experience he got in New York was very helpful,” said Kristol. “He really understands business and the business world in a way he might not have if he’d gotten a cushy job in the administration.”Senor’s name was back in the mix by April 2006. Josh Bolten, then Bush’s chief of staff, tracked him down on his honeymoon with Brown in Mauritius to see if he’d be interested in rejoining Team Bush. “Campbell was like, ‘What? Doesn’t he know it’s our honeymoon?’ ” Senor remembered. He decided to stay in New York, where Brown was then an anchor for CNN. A few weeks later, Romney’s chief of staff, Beth Myers, called from Boston to ask whether Senor would be willing to come talk to the Massachusetts governor, who was considering a presidential run. “The two of them hit it off immediately,” Myers said. “I can’t think of anyone who Mitt has ever met that he hit it off with so immediately as Dan Senor.”Senor felt the same way. “We spent two hours talking about the world, the Middle East, everything, India, Pakistan, a whole range of foreign-policy issues,” Senor told me. “He was a different kind of political figure than ones I’d dealt with before. His approach to thinking through problems was so—well, his critics would say technocratic. But for better or worse it was refreshing.” By the following January, Senor was arranging to take Romney to the annual Herzliya security conference in Israel and helped prepare the governor for his debates during the Republican primary season.At the same time, Senor and Singer were writing their proposal for Start-Up Nation. The idea, both men said, originated with a trip Senor organized for his Harvard Business School classmates after graduating in 2001. The notion of looking at Israel through a business lens was new to most people, but natural to Senor, whose father had moved on to run the Canadian affiliate of the Weizmann Institute of Science after his stint with Israel Bonds. (He also opened the Tehran office of the Joint Distribution Committee in the late 1950s.)“Had I taken an administration job, the book never would have been written,” Senor said. They wound up turning in the proposal shortly after Romney dropped out of the 2008 presidential primaries. Start-Up Nation was picked up immediately by Twelve, the boutique imprint launched by Jonathan Karp, and came out the following year. It was an instant success, not just among Jews but in the general audience. “It’s a book about Israel that’s not for Jews,” Senor said. “I didn’t want it to be in the Judaica section of the bookstore, or the Israel or the Middle East section.” It wound up in the business section, right between Too Big to Fail and Superfreakonomics.***Senor’s attachment to the Romney campaign in some ways returns him to the place he might have imagined being when he came home from Baghdad in 2004. “I want to be involved in policymaking on issues that I care about,” Senor told me. He has input into some of Romney’s public speeches, including the one he will give on Sunday in Jerusalem, and is a regular surrogate across the cable news spectrum.But while his involvement with the Romney campaign is steadily increasing—Senor said he visits the campaign headquarters in Boston at least once a week but expects to spend more time there after returning from this weekend’s trip to Israel—he continues to pursue his own business interests. He retains a financial interest in the firm he launched with Heinz, Rosemont Capital. Meanwhile, the Start-Up brand continues to grow: Rights to the book have been sold in 26 countries, most recently Croatia, and a film crew has already begun shooting a documentary based on the book in Israel. Senor is also developing a feature film version along the lines of The Social Network. Meanwhile, he and Singer are talking about doing a second book. “Dan, with Saul, has the opportunity to create a real business authorship brand,” said Cary Goldstein, now Twelve’s publisher. “And if I can stay in the Dan Senor business, I will.”For Senor, it may be a better industry than Washington. He has two young sons at home, part of his publicly stated reason for not pursuing the New York Senate seat in 2010. He has the freedom to pick his projects and to do many different things at once, at home and abroad. “Dan,” his friend Heinz said, “has got it pretty good.”***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Allison Hoffman is a senior editor at Tablet Magazine. Her Twitter feed is @allisont_dc.