The last time I spoke with Anthony Scaramucci he began the conversation by saying, “This is off the record, right?” I assured him that it was. “I have to ask that now, you know,” he said.

A week or so before, New Yorker writer Ryan Lizza had written up an inflammatory phone call with Scaramucci. During the call, Scaramucci had labeled then White House chief of staff Reince Priebus “a fucking paranoid schizophrenic” and suggested that White House advisor Steve Bannon’s infatuation with media coverage was the equivalent of self-fellation. (On this, Scaramucci may have been more crude than wrong.) Priebus exited in short order, and then almost immediately the new chief of staff, John Kelly, fired Scaramucci as the White House communications director after just 10 days on the job.

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It was painful to watch, and not just because the whole thing was so amateurish. It was painful because Worth and Anthony Scaramucci have an amicable history. In 2014, when Scaramucci was running fund-of-funds firm SkyBridge Capital and had just published a small book called The Little Book of Hedge Funds, he contributed a “20 Questions” column to this magazine and visited our offices for a get-to-know-you briefing. Scaramucci was funny, smart, charming, self-deprecating—it was impossible not to like the guy. And the Mooch, as he’s sometimes called, had what he presented, passionately, as a populist vision for SkyBridge: making it possible for relatively small investors to access the same hedge funds that billionaires put their money into. It was unquestionably a self-serving proposition, and in my opinion, not a wise one for people who are not wealthy. Certainly, given the fee structure of funds of funds, it was a costly one.

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But Scaramucci made the best case for SkyBridge that you could make. He’s a helluva salesman, in no small part because he commits himself entirely to whatever he is selling.

Over the years, I crossed paths with Scaramucci at SALT, the high-profile conference he founded for the hedge fund industry to cheer itself on. He invited me (and other reporters) to a Mets game, which we watched from the perspective of his private box; Scaramucci is a part owner of the team. He was good company—high energy, with an unusual ability to be self-deprecatory one moment and self-important the next, conscious of at least the former.

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Scaramucci appeared as a speaker at several Worth events. The most recent was in Greenwich, Conn., about three weeks before the 2016 election; Scaramucci was part of an election-themed panel along with Stuart Stevens, a political consultant who works for moderate Republicans, and banker/entrepreneur Robert Wolf, who advised President Obama on economic issues. There was little doubt that Hillary Clinton would win. Still, Scaramucci made the best case for Trump that you could make, I think. He’d been on the campaign trail; he’d seen the people who felt left behind as affluent America moved forward. Clinton was not speaking to those people, he said. Trump was. And that mattered. Scaramucci, who comes from a working-class Long Island family, sounded like he believed what he said.

But he was an imperfect messenger. A Romney supporter in 2012, Scaramucci had supported two other Republicans, Wisconsin governor Scott Walker and Florida ex-governor Jeb Bush, before signing on with Trump. He had warned his party about “the reckless behavior of a man who knows a thing or two about bankruptcy.” So it was hard not to wonder whether Scaramucci really believed in the candidate or if he was just so desperate to be in the mix, so needy for a new stage that he would hitch his wagon to anyone—no matter how unprincipled—who had a shot at winning. And of course, it was a little hard to take, the hedge fund impresario who flies private and hobnobs with billionaires, talking up the forgotten Americans.

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But the point seemed moot; even Scaramucci didn’t seem to think that Trump would win. When he announced that he had to leave to join Chris Christie and others at his midtown restaurant, the Hunt & Fish Club, for a meeting of the Trump transition team, you could almost see a collective raised eyebrow throughout the audience: “Why bother?”

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We were all wrong, of course; Greenwich may not be the best place from which to take the pulse of the nation. In anticipation of a summons to Washington, Scaramucci sold SkyBridge to the Chinese conglomerate HNA Group (it was probably time to exit the fund-of-funds sphere, anyway) and waited. For months—allegedly during which Reince Priebus “cock-blocked” him—he remained a Trump mouthpiece, who, throughout the travel ban, Russia, the Comey firing, continued to proclaim that Trump was fighting for the little guy, draining the swamp. Scaramucci was as passionate as ever, but there was something uncomfortable about watching him plead Trump’s case.

His first day on the job, he professed, “I love the president.”

Whatever his faults, Scaramucci always struck me as a man with a big heart—proud of his Italian immigrant roots, heart on his sleeve, philanthropic. He’s proud of his financial success, but he’s a small-d democrat, a more plausible man of the people than Trump could ever be. More and more, though, his arguments for the president seemed willfully blind. I kept thinking, Does he really want a White House job that much?

In late July, he finally got one. His first day on the job, he professed, “I love the president.” You couldn’t accuse the Mooch of fellating himself, but you could say he was blowing Trump.

And then, 10 days after that indignity, he was gone, following a rant that was obscene not just because of its language but because of its vulgar self-importance, the fact that Scaramucci dubbed a leak about himself “a major catastrophe for the American country” and threatened the wrath of the nation’s law-enforcement agencies in retaliation. Usually the mighty get to enjoy their perch at least a little while before they fall, but how could even Trump have employed Scaramucci after that?

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As I write this, Scaramucci is in Italy recovering. What’s his next move? I have no idea, but I know it’ll be worth watching: Scaramucci has an admirable history of bouncing back from adversity. Still, the real challenge for the Mooch isn’t finding his next gig. It’s not excoriating reporter Ryan Lizza or gutting Washington insiders. It’s examining his own journey, the apologies he made in pursuit of power, and answering the question, “What the hell did I just do?”