The Surprisingly Tolerable Second Act of Anthony Scaramucci

How to bounce back when 11 disastrous days in the White House has turned you into a national punchline. (Hint: Self-awareness helps.)
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Photos by Mark Mann

It’s early to be on cable news, but really, it’s early to be anywhere. It’s 5:56 a.m., yet neither the hour nor the darkly lit green room deters Anthony Scaramucci from firing on all cylinders, by which I mean schmoozing and cracking jokes and asking people for selfies. As his wife had warned me: “He’s nuts, even early in the morning.”

Scaramucci, the (short-lived) former White House communications director, simply loves to talk. He commiserates about the Mets with a production guy (“Dude, what’s going on with our team?”), asks the woman patting concealer under his eyes about her young son (“When was his birthday? God bless him.”). As he gabs to another makeup artist, she suddenly notices me and my notebook. Alarmed, her eyes dart back to Scaramucci. “Why is she taking notes?”

He explains that I’m a reporter, and she blanches. “Everything I even mutter is off the record,” she says. Scaramucci lays on the charm. “She knows that,” he assures her.

But: I don’t know, because we hadn’t actually discussed it. It’s a jarring redux of the blunder that ended his 11-day tenure at the White House in July 2017. Thinking he was off the record (according to widely understood media protocol, he wasn’t), he launched into a profanity-laced screed while talking to a New Yorker reporter. He was out of a job days later.

Two years after this flameout — or, as he likes to call it, when he “got his ass lit up in the White House” — Scaramucci, 55, apparently hasn’t yet figured out how to tell a journalist when something is off the record. But no matter: He has successfully converted his 15 minutes of fame into a steady stream of speeches, talks and cable news appearances. If you’re paying attention, you can see Scaramucci everywhere: at an Upper East Side social club, sermonizing about how to reelect President Trump; sharing a house with Olympic swimmer Ryan Lochte and Kato Kaelin, the O.J. Simpson murder trial witness, on the reality show “Celebrity Big Brother”; in a truly surreal video for the New York Post where he did an interpretive dance for each of his 11 days in the White House; on the cover of the May issue of Resident, an “aspirational luxury lifestyle” magazine, the bejeweled American flag pin on his lapel aglitter; and, of course, on Fox News, waxing political about the latest White House drama.

He’s honed quippy, self-deprecating laugh lines — he’s got “orange Cheeto stain” on his hands from his association with Trump; he thought his White House tenure would last “longer than a carton of milk” — and uses them constantly. Throughout our time together, everyone in his orbit seems utterly taken with him. “He’s one of those guys who’s always going to try to charm you, even if you don’t agree with him,” says Bill Maher, who does not agree with him most of the time. Scaramucci appeared on Maher’s HBO show last year, and they became friendly, going to a Mets game together. “He’s a likable guy,” Maher says.

It’s possible that in the history of American politics, no one has done more with less experience at the seat of power. Scaramucci has turned his moment of public humiliation into a rousing comeback tale, rising (at least in some circles) above his status as a national punchline. You could attribute it to pure persistence, pure ego or a complete absence of shame. But at heart, it’s a triumph of self-deprecation. In a political climate where absolute certainty is rewarded and no one ever apologizes — or even signals self-doubt — about anything, Scaramucci is creating a second act simply by being in on the joke.

When I arrive at the News Corp. building in Midtown Manhattan for his Fox Business appearance, I greet Scaramucci — a.k.a. “the Mooch,” a sobriquet coined by his second-grade P.E. teacher, who decided his last name was too long — in the lobby. He’s holding a venti Starbucks iced coffee in one hand and a bottle of Evian in the other; drinking liters of water a day, he tells me, is an absolute must for great skin. He’s hobnobbing with another guest on the show, financier Alfred Eskandar. As I introduce myself to Eskandar and explain that I’m writing a story for The Washington Post Magazine, the Mooch interjects: “As Trump says, the ‘Amazon Washington Post.’ ” He lowers his voice conspiratorially and says of Trump, “He’s so f—ing crazy.”

It’s not that he thinks Trump is crazy crazy — like, impeach-him crazy. The president’s policies have been good for the country, the Mooch insists (though he notes that he takes issue with Trump’s treatment of the media, his approach on trade and his rollback of LGBT rights). It’s Trump’s style he chafes at. Of the zingers he frequently deploys about the president and his time in the White House, one of his favorites is: “Trump’s campaign slogan should be ‘Same policies, less crazy.’ ”

Following his three-hour stint on Fox Business, we meet back up. Fox kicked me out of the building after learning I was a reporter; Scaramucci hadn’t told them I’d be coming. I clarify our rules of engagement: We’re entirely on the record, unless we explicitly agree otherwise. Of course, Scaramucci says: “We’re having an on-the-record discussion. Talk about anything you want.”

We drive (or rather, are driven; the Mooch has a dedicated driver behind the wheel of a hulking Cadillac Escalade) to the Bronx, where he’s due to speak at the Riverdale Country School, a private high school so elite it looks like we’re on a college campus. He’s still wearing his TV makeup. He loves getting his makeup done — “You can never have enough makeup or hair spray,” he tells me — and sometimes books himself on a news show just so he can put his face on.

The gym at the school is nearly full. He tells the 200 or so kids seated in the risers about his career, his politics and his “not appropriate” New Yorker interview. “Raise your hand if you’ve never cursed in your life,” he commands the crowd. (In the car back to Manhattan, he flips it to me: “You didn’t raise your hand. I think you must have said at least one curse word in your life.” When I tell him that I curse like a sailor when I’m not in a professional setting, he cackles and gives me a fist bump.) At the end of his remarks, some kids cheer, some boo, but nearly all want selfies. He stays for a full hour after his speech to keep talking to the 30 students who swarm him.

Anthony Scaramucci in the White House briefing room in 2017. (Jabin Botsford/The Washington Post)
Scaramucci on morning television outside the White House in 2017. (Mark Wilson/Getty Images)
Scaramucci with former New Jersey governor Chris Christie and others at Scaramucci’s Las Vegas hedge fund conference in May. (David Becker for The Washington Post)
Clockwise from top: Anthony Scaramucci in the White House briefing room in 2017; with former New Jersey governor Chris Christie and others at Scaramucci’s Las Vegas hedge fund conference in May; on morning television outside the White House in 2017. (Clockwise from top: Jabin Botsford/The Washington Post; David Becker for The Washington Post; Mark Wilson/Getty Images)

Next, he hustles to 30 Rockefeller Plaza for an appearance on MSNBC as one of five panelists weighing in on Donald Trump Jr. agreeing to testify before the Senate Intelligence Committee. Then he films a segment for a British news show. Then it’s on to the Cosmopolitan Club, a swanky social club on the Upper East Side, where he speculates on Trump’s 2020 prospects. Before the event starts, I notice that nearly every member of the packed crowd is holding a copy of his book, “Trump: The Blue-Collar President.” The book — which Center Street, an imprint of Hachette, published in the fall — is part memoir, part Trump hagiography. (The president, he writes, “might have been the only truly authentic candidate in history.”) Wow, I think. These people really love the Mooch. Just then a woman takes the lectern to introduce him and thanks him for donating all the copies of his book so that everyone could take one home. He steps to the mic from behind her. “My wife said I needed to get them out of the basement.”

He gives a version of what I’ve come to discern as his stump speech: Trump, he says, needs to “dial down the rhetoric.” Washington, he discovered the hard way, isn’t a swamp, but actually a “gold-plated hot tub without a drain.” Americans need to “put the country back together” and heal our deep political divisions. He tells the whole story of his New Yorker interview. “I could do this all night,” he says. Afterward, the crowd, mostly glitzy old-money types, rushes him for photos and autographs. Proclaims one man who looks to be in his 60s: “You’re a pioneer!”

At every stop, he’s treated like a political authority, a Trump Svengali who can impart his deep wisdom about how Washington works. Never mind that in reality he was there for about as long as a self-guided tour. “I don’t have any Washington smarts,” he tells me. “Just saying I’m politically naive would be an understatement.”

He doesn’t have illusions about the source of his popularity. “If I wasn’t blown from the White House like that,” he says, “these people don’t even know who I am.” We’re in the back of the Escalade, stuck in traffic on the West Side Highway on the way back from the Bronx. He’d never be invited to speak at these events had he not spent those 11 days as White House communications director.

In May, the Mooch put on the 10th edition of his Las Vegas hedge fund conference, SkyBridge Alternatives, known as SALT. He’s back to running SkyBridge Capital, the investment firm he founded before his foray into politics. The company is a “fund of funds,” which invests in hedge funds for people who are wealthy but not the 1 percent. When those people see him at a talk, or on TV, maybe they’ll think about putting their money with him. Even infamy is good for business.

As we inch through the lunchtime gridlock, I ask him what the biggest lesson he learned in the White House was. He thinks for a beat. “I didn’t learn the lesson,” he says. “Don’t talk to reporters.” He cracks a wide smile and gives me another fist bump.

Scaramucci has never been one to back down. “I didn’t want the machinery around what happened to me to totally define me,” he says.

The Mooch was doing well in business, but, well, he wanted more. He had already far surpassed the expectations of the average working-class Italian American kid from Port Washington, a hamlet on Long Island. His mom, Marie, told me that Anthony wasn’t drawn to the spotlight growing up — it found him naturally. “He was very, very, very well liked as a kid, and he was very, very well liked in the neighborhood,” she recalls. She says his friends called him “Moses” because he was so strait-laced.

He was the captain of his high school football team and student government president, had the popular girlfriend. Life always seemed to work out for him. “He never had that fear of embarrassment,” says his friend Paul Montoya, who has known him since kindergarten. “Anthony’s got so much confidence that he’s going to say what he feels.”

The Mooch studied economics at Tufts and went on to Harvard Law, where he stood out with his Long Island accent and blue-collar background. Richard Kahlenberg, a classmate at Harvard, tells me the Mooch regularly cracked jokes in class. “He was willing to puncture the pretensions of this very serious set of students and professors,” he says. “He certainly didn’t take himself too seriously.”

After law school, he failed the bar twice before finally passing; he was also fired from his first post-law-school job, at Goldman Sachs (but was later rehired in a different division). He started two investment firms, including his current company, and made himself a millionaire. In the run-up to the 2016 presidential election, he initially signed on as a fundraiser for then-Wisconsin Gov. Scott Walker, who dropped out of the race just two months after joining, and next floated to former Florida governor Jeb Bush. When Bush dropped out, the Mooch turned to Trump, whom he’d known for two decades. (Scaramucci had once approached him to invest in his nascent hedge fund, and the two ran in the same wealthy Manhattan circles.) “He’s clearly drawn to having a voice and a role,” says Andrew Klein, who co-founded SkyBridge with him. “I think, through Trump, he saw a way to kind of get in the game at a higher level.”

During the transition, he was promised a job running the White House Office of Public Liaison, but he says that then-chief of staff Reince Priebus and chief strategist Steve Bannon thwarted him because he was “a wild card” who wasn’t entrenched in politics, and they were threatened by his long-standing relationship with Trump. In July 2017, despite their objections, Trump made him communications director. (Neither Priebus nor Bannon responded to requests for comment.)

After his first, and only, news conference, the late-night hosts had a field day with his tough-talking persona. Seth Meyers called him “the human embodiment of a double-parked BMW,” while Stephen Colbert likened him to “a lawyer whose ad is above the urinal.” Sean Spicer resigned as press secretary in protest of Scaramucci’s dearth of communications experience. Priebus followed days later.

The Mooch came in with a mission: Find — and fire — whoever was leaking to the media. That quest would lead to his downfall when he called then-New Yorker reporter Ryan Lizza late one evening, demanding to know who had leaked a small piece of news. It devolved from there: He launched into an extended, obscene tirade, lambasting his fellow West Wing aides in graphic terms. The Mooch thought it was off the record, but he and Lizza had never discussed it. (He insists it was “implied” and that Lizza knew this.) In the time I spend with him, he brings up this moment approximately 47 times. He felt betrayed by Lizza, whom he thought he could trust. “You’re talking to an Italian American from the next town over whose dad knows your dad for 50 years,” he says. “Al Scaramucci and Frank Lizza were close friends.” (Lizza told me he’d never heard the name Scaramucci until he met the Mooch at CNN one night. “I don’t know who his family is,” he says.) Another time, of Lizza’s publishing the conversation: “Was that a nice thing to do?”

The call, along with his evocative quotes, rocketed through the political world, and he was fired a few days later. (The Mooch maintains that, because he arrived at the White House at 6 a.m. the day he was fired and stayed until 2 p.m., it should count as a day he worked there, and so: 11 days.) He saw it coming, of course. He’s self-aware enough to know he made a mistake. “I never said, ‘Hey, by the way. On the tape, this is off the record.’ That’s my stupidity. I own that.” (He also points out the irony of getting fired for making off-color remarks by a president who has arguably said much worse: “It’s sort of funny in the Trump administration, where we were grabbing them by the p—y in the campaign. Now, you get blown out for saying something like that.” Then again, he concedes, he’s not the president.)

What came next was brutal. His marriage was in a shambles: His wife of three years, Deidre, had filed for divorce, and the tumult was splashed across Page Six. He had missed the birth of their son, who was due in August but was born right in the middle of his brief tenure, when Deidre went into premature labor. The Mooch was at a Boy Scout event with the president and couldn’t make it to New York in time for the unexpected birth. Headlines lambasted him for appearing to love Trump more than his newborn. That’s hard stuff to read about yourself, he tells me, that you don’t care about your family.

Otherwise, though, he’s surprisingly sanguine about it all. He likens himself to George Bailey, the doleful protagonist in “It’s a Wonderful Life”: His 11 days in office and national humiliation, he tells me earnestly, were “a wake-up call to make me realize I need to appreciate more of what I had.” He reconciled with his wife after going to a marital “life coach.” Last year, they launched a podcast, “Mooch and the Mrs.,” where they talk about their relationship and squabble over the news. “He was just really caught up in the whole scene and totally enamored with the relevancy of everything he was doing,” Deidre tells me of her husband’s time with Trump. “You get this inflated sense of self, which is totally not who he is.”

He could have retreated to the shadows. Some would say he should have. But he’s never been one to back down. “I didn’t want the machinery around what happened to me to totally define me,” he says. “I want my kids to know that you can take risks, fall on your ass and still be okay.”

Does it ever hurt, I ask, to be known as a punchline? “It’s f—ing funny,” he says. “What’re you going to do? You going to cry about it? You’re asking me if my feelings are hurt that people think I’m an idiot. Who gives a s—. F—ing did the best I could.” He’s not the type, in other words, to be easily embarrassed. He’s an entrepreneur who failed the bar twice before finally passing, who was fired from his first job out of law school. He’s used to bouncing back. And all he can do, really, is laugh along with everyone else.

I ask him what the biggest lesson he learned in the White House was. He thinks for a beat. “I didn’t learn the lesson,” he says. “Don’t talk to reporters.”

The Mooch gives a bad first impression, he’ll be the first to admit. He’s a Capricorn with Aries rising, and if you understand the signs, you get that that’s a dangerous combination. (He’s very attuned to astrology, and after finding out I’m a Taurus informs me that I’m extremely stubborn and loyal, which, yep.) When they first meet him, “people find me to be way more fiery than I actually am,” he explains. “I’m way more down to earth.”

He’s an easy target for satire. His tough-talking New York accent, his oleaginous flattery of Trump, his unabashed love for the movie “Goodfellas” — it’s easy to flatten him into a gym-tan-laundry “Jersey Shore” stereotype. “He’s very different than the public caricature,” says former deputy attorney general Rod Rosenstein, who was in the Mooch’s class at Harvard Law. “He really has a good heart.” He’s generous with his time and money. One of his good friends died on 9/11 and left behind young kids. The Mooch stepped in to make sure they had a father figure in their life, taking them to Disney World every year. They’re still close today.

Over the few days I spend with him, the Mooch is warm and welcoming. He asks about where I’m from, about the details of my upcoming wedding. (His marriage advice? “You have to show up every single day for your relationship.”) He shares genuine concerns about the country’s increasingly hostile partisan divide. “I think that he probably gets a bad rap because he is prone to exaggeration or dramatics, but he is a very thoughtful, intelligent, somewhat introverted human being,” says Deidre, whom he met when she started working under him at SkyBridge. (“This was before the #MeToo movement,” she notes.) She insists he’d be much happier staying home to read a biography of Abraham Lincoln than going out to a party.

He’s also really funny. In the car on the way to tape his podcast one afternoon, he tells me about the time he and Paul Montoya went to a high school Halloween party in drag. “I had a f—ing very hot dress on. I had fake boobies. I had pantyhose. I had, like, makeup on.”

Man, I say. I’d love to talk to one of your high school buddies. He pulls out his iPhone and dials Paul, who picks up after the second ring. “I’m in the back of the car with a woman by the name of Rebecca Nelson,” he says, putting Paul on speaker. “I’m telling her about how we went in drag to the Halloween party. You remember that?” Paul doesn’t miss a beat. “I remember it all. And we made good-looking women,” he says.

For a working-class Italian American kid from Port Washington, the Mooch thinks, he’s done pretty well. “From my vantage point,” he says, “whether I lasted one minute in the White House, 11 days, four seconds, the whole thing is, like, a miracle.” He’s been invited to parties that no way he would’ve been invited to before. “I probably shouldn’t say this to you, but I’ll say it to you,” he says, lowering his voice in the back of the Escalade. “I haven’t gotten a speeding ticket since I left the White House.” He’ll get pulled over by police officers after doing 90, he says, and when he rolls down his window to plead his case, the officers can’t believe their luck that they’ve stopped the Mooch. (They always want a photo.)

It’s become inevitable for former White House aides to cash in on their status and know-how in some way or another. When they exit the revolving door, they exchange their political savvy for a cushy lobbying job. But the Mooch didn’t need Big Pharma or Big Oil or big anything. He was already wealthy beyond measure. The payoff, for him, comes in a different form. Rapt audiences. Reality show fame. People who stop him on the street and say: Hey, aren’t you that Trump guy? Innumerable selfies.

With his 11-day political education, he’s the ultimate example of how, in America, even the perception of proximity to political power can take you far. But it’s his personality that’s made it possible: He’s so self-deprecating and good-natured about the gaffe that put him on the map, so utterly self-aware, that he wins people over.

Of course, being aware of what you’ve done doesn’t make it retroactively okay; being able to laugh at yourself doesn’t excuse complicity in an administration that, in the eyes of many Americans, has done truly appalling things. Shame does serve an important purpose, after all. And yet, in a society where our public figures take themselves all too seriously, there’s value in the art of self-deprecation, in self-awareness. Perhaps the fact that Anthony Scaramucci is still talking, and people are still listening, shows just how starved we are for these things. Even if it comes from someone who’s kind of ridiculous, someone whose politics you may abhor, couldn’t we all use a reminder to laugh at ourselves?

In his memoir, the Mooch characterizes himself as “a supercharged sales machine who might drive you nuts or charm you, or both. But I guarantee one thing,” he writes. “You’re not going to forget me.” He’ll keep talking till he’s sure of it.

Rebecca Nelson is a journalist in New York.

Scaramucci walking with his wife, Deidre, at the hedge fund conference in Las Vegas. (David Becker for The Washington Post)
Credits: Story by Rebecca Nelson. Photos by Mark Mann. Designed by Christian Font.