‘If somebody walks into your office and says they’re friends with Donald Trump, they’re either exaggerating the relationship, or they don’t understand the relationship,” says Anthony Scaramucci. “Because nobody is friends with Donald. You’re a transaction in this guy’s field of vision.”
Scaramucci should know. He has been non-friends with Trump for more than 30 years, though these days he’s more an outright enemy. Just as the attention-devouring president once stalked Hillary Clinton on the debate stage, Trump looms large in Scaramucci’s story. The two men seem to haunt each other. When we meet in London during a stopover in his hectic schedule, the conversation rarely drifts away from Trump for more than a few minutes. Conversely, the 62-year-old financier and broadcaster has become one of Trump’s most vocal and penetrating critics. “We fight like New Yorkers,” Scaramucci says. “He doesn’t really come back at me, because he knows I’m going to come back at him.” Unlike Trump’s presumptive friends, Scaramucci does understand Trump, he claims. “There’s something called ‘Trump derangement syndrome’; I think I have ‘Trump reality syndrome’. I know what he is, I know what he does, I know what he’s capable of and I know the danger of him.”
Most people’s abiding memory of Scaramucci will be his brief and spectacular spell as the White House communications director in July 2017, where his brash, energetic manner and unapologetically Italian-American Noo Yawk accent made him an object of fascination and ridicule. Saturday Night Live called him “human cocaine”. But if Liz Truss didn’t outlast a lettuce, Scaramucci’s political lifespan was barely that of a ripe avocado: 11 days. He has fully owned it. He’s even adopted it as a unit of measurement – when the British prime minister abruptly quit in October 2022, he tweeted: “Liz Truss lasted 4.1 Scaramuccis”.
He has been on a journey since then, though not sartorially, perhaps. There’s still an air of 1980s Wall Street about Scaramucci: luxuriant, slicked-back hair, Italian suit, silk tie, ornate cufflinks, smooth complexion – a smartwatch is practically his only concession to the 21st century. He’s no less garrulous than he ever was, but he is a calmer, humbler presence these days, as listeners of his hit podcast The Rest Is Politics US will attest. Paired with Katty Kay, the BBC’s former Washington correspondent (who sounds as quintessentially British as the Mooch does quintessentially American), they make an engaging odd couple. And unlike many a podcast bro, Scaramucci is respectful and almost deferential to Kay. “I think she’s incredibly smart and I want to hear what she has to say,” he says simply.
Scaramucci really is a product of 1980s Wall Street. In fact, when he was studying law at Harvard in 1987, aged 23, the film director Oliver Stone visited the college and screened his new movie of the same name for students. Scaramucci describes it as “a classic American story”. After the screening, “I met Oliver Stone in that theatre and shook his hand.” In 2010, Scaramucci even had a cameo in the film’s sequel Wall Street: Money Never Sleeps, playing himself. (He also paid $100,000 for product placement of his hedge fund, SkyBridge Capital.)
He had already come a long way by this stage. Born in Long Island, the son of a crane operator father and a cosmetologist mother, he was not poor but far from rich. He was always money-focused, he says, and always working: a paper round, stacking shelves, working at his uncle’s motorcycle shop. “I knew, if I’m being brutally honest, that my parents were going to run out of money.” His parents were ambitious for him and his siblings to go to college and they were the first generation of the family to do so: first, he went to Tufts University in Boston to study economics, then Harvard Law School (at the same time as Barack Obama, coincidentally), then straight into a job on actual Wall Street, at Goldman Sachs.
“What Wall Street was in my mind was very different than it actually was,” he says. Even more than at Harvard, he was a fish out of water. “My first job interview, I looked like a fucking Brooklyn undertaker. I had a black polyester suit and a polyester shirt on. It took me a long time to get from polyester to Brioni,” he says, flipping open the inside of his jacket to show me the Italian label. “I didn’t have the etiquette. I didn’t go to a boarding school. I didn’t have a father that worked on Wall Street, and so this was a very big rite of passage for somebody like me, and it was a very big transition.”
Early on, it seems, Scaramucci realised that the privileged elites were really no smarter than he was. “You have to get comfortable with being an outsider. Trump is an outsider, but he’s an uncomfortable outsider, and so he has a chip on his shoulder. He’s angry that he can’t get into the salons of the uber-wealthy, the establishment. So now he’s trying to lord over them. He couldn’t get into certain golf clubs that the blue bloods were members of, so he built himself golf courses.”
In terms of wealth and privilege, Scaramucci and Trump are poles apart, but there are striking parallels. Both grew up under disciplinarian fathers – “My father used to beat the shit out of me,” Scaramucci says, although “Fred Trump had more power in his community; my dad was a union worker who was a bit of a hard-ass, a smoker, a drinker. It was more Angela’s Ashes sort of shit.” Both of them had elder brothers who bore the brunt of their parents’ bullying. “The older brother is a little bit of a heat shield for the younger siblings,” Scaramucci says. Trump’s brother Fred Jr had issues with alcoholism and died aged 42; Scaramucci’s brother also developed addiction issues, but has been sober since 2007. And like Donald Trump, Scaramucci went the other way as a result: he doesn’t smoke and rarely drinks, “because I come from a family of drug addicts and alcoholics”. He is, though, he admits, a workaholic. “It manifests itself in different ways.”
Scaramucci first met Trump in 1995, when he was 31. His boss at Goldman Sachs took him to a meeting at Trump Tower. “I was in awe, I’m not gonna bullshit you. He was probably one of the most famous people in New York.” Trump was an omnipresent public figure at the time – on the front pages of the tabloids, on television opening grand new buildings, hawking his The Art of the Deal book. “He was the quintessential emblem of success. We didn’t know about the bankruptcies and the nefarious behaviour; we saw the glitz.”
Their paths crossed again 10 years later, when Scaramucci was doing punditry for CNBC and Trump was hosting The Apprentice on NBC. They were at a few charity events and baseball games together. “I was charmed by him. I’m not going to pretend otherwise.” In 2012, they did a few fundraisers for the presidential candidate Mitt Romney in Trump’s famously overgilded apartment (Scaramucci describes it as “like Liberace got married to Louis XIV”). Then, in 2015, Trump invited him to breakfast and told him he was leaving The Apprentice and running for president. “I looked at him and laughed,” says Scaramucci. “I thought it was just a publicity stunt.”
Scaramucci and Trump were also broadly aligned in their politics at this stage – socially liberal but fiscally conservative and business-oriented. Scaramucci worked with the New York governor Andrew Cuomo on gay rights, he says, and has supported women’s reproductive freedoms. He backed Obama in 2008, Romney in 2012, and before the 2016 elections he switched from supporting Hillary Clinton to the Republicans Scott Walker and then Jeb Bush (“he would have made a good president”). When Trump became the Republican party’s presumptive nominee, in May 2016, he asked Scaramucci to come and work for his campaign.
Trump had been on a similar trajectory, he observes: He was more of a Democrat in the early 00s, “then he moved into the Republican party but he was a centrist Republican. The wackadoodle Maga [Make America Great Again] and the nationalism and all this proto-authoritarianism came later.” This was one of the reasons Scaramucci agreed to work for him, despite his reservations: “We were talking ourselves into the idea that he was going to be OK.”
Scaramucci had been on team Trump for about a year before his disastrous spell as communications director. The finer points of those 11 days have been well raked over but, essentially, he made an injudicious phone call to a New Yorker journalist in which he laid into other Trump officials, most memorably calling the White House chief of staff Reince Priebus “a fucking paranoid schizophrenic”, and saying: “I’m not Steve Bannon, I’m not trying to suck my own cock.” He realised too late that the conversation was not off the record – not a great look for a communications director.
Scaramucci didn’t just pay a professional price for his association with Trump. His wife, Deidre, had also been against it. “She hates him almost as much as Melania hates him,” he jokes. “And we were fighting for other reasons. She filed for divorce on me.” Scaramucci also missed the birth of their second son during this time because he was with Trump, and reportedly congratulated his wife by text. All of this conspired to make him briefly, spectacularly and damagingly famous.
“It was a very hard time in my life,” he says with calm understatement. But he is wiser for it. “I feel like that whole process gave me a platform to articulate the danger of Trump, so there’s a silver lining in there. A lot of the stuff that happened doesn’t reflect well on me: bad decision-making, ego-based decisions, pride-based decisions. I’m not sitting here with any pedantic arrogance; I’m sitting here very humbly saying to you: ‘Hey, I’ve gotten my ass kicked in my life. Here are the things that I’ve lived through, here is the danger that I’m seeing.’ I’m going to articulate it, if people are willing to listen.”
Does he think about what might have happened if he hadn’t been fired? “I would have never been able to stay,” he says. “We were fighting about everything. The Charlottesville thing: forget it.” He’s talking about the infamous white supremacist rally that took place a month after he was fired, about which Trump stated there were “very fine people on both sides”. “As screwed up as my family was … We know right from wrong.” He cut ties definitively two years later, after Trump’s racist attacks against four Democratic congresswomen of colour, whom he told to “go back and help fix the totally broken and crime-infested places from which they came”.
But it was also a personality clash. It was Trump’s way or the highway, Scaramucci says. “So whether I was going to take the highway after 11 days or two months, I was going out the door. Anybody that had a backbone or a set of principles was never going to be able to work for Trump. It was always going to end badly.”
By that measure, there are plenty of people around Trump now who lack such principles. “Power corrupts,” he says. “There are people in life that want to drive around in the presidential motorcade. They want to lift off from the south lawn in the helicopter on their way to Air Force One. They live their life around the idea of significance. I don’t actually give a shit about that. Like I said, I’m a comfortable outsider.”
But you can’t keep the Mooch down. He clawed his way back, repaired his marriage and his relationship with his family (he has five children, three from an earlier marriage). Although SkyBridge, which he founded in 2005, became entangled with the crypto fraudster Sam Bankman-Fried, whose firm FTX owned 30% of SkyBridge when it collapsed in 2022. “I liked him and I trusted him,” he says of Bankman-Fried. “I thought he was more honest than he was. I got that wrong.” He was not alone in that, he stresses, “and by the way, everyone got their money back”. But as Oscar Wilde would say, one dodgy association looks like an accident, two looks like carelessness. “I think I have some bad judgment, but I’m also a big risk taker,” he says. “And you have to remember, to go from the house that I grew up in to where I am today, you’re not getting there without taking risks.” He now lives in a nice house in the Hamptons, and in 2022 he bought himself his dream car, a black Lamborghini. The irony is that Trump’s survival has been great for Scaramucci’s career. “I often say he is an executive producer on every political podcast in the world,” he acknowledges.
So comprehensively has Scaramucci owned his mistakes – and recovery from them – failure is almost part of his brand now. In 2024 he wrote a book called From Wall Street to the White House and Back: The Scaramucci Guide to Unbreakable Resilience. Last year he launched The Resilience Lab, a $49 online course on how to survive failure (“I’ll show you the unwritten rules of the game so you can build your own unbreakable career”).
Later this year he has a new book out called All the Wrong Moves, accompanied by a UK tour. It’s not about his wrong moves this time, but those of his country: the unwise decisions made by Republicans and Democrats that led to Trump – from nationalism and xenophobia, to free-market trade agreements, to electoral funding, foreign wars, disaffection with the social contract. Despite his own elitist detachment, Trump was speaking to people like his own father, Scaramucci realised. “While he provides no policy solutions for them. He is an avatar for their anger.”
Scaramucci does not anticipate Trump’s downfall just yet, though. “You can never count him out. The Epstein files won’t knock him out. I’ve said that consistently.” We’re speaking just before the US and Israel launched their attacks on Iran on Saturday. Scaramucci had predicted that Trump would not pull back, having put so many military assets in the region – “It’s just not in his personality. He’s too impetuous. He’s too impulsive.” In an online essay this weekend he questioned the legality of the war and warned of long-term damage to America’s standing. “When a democracy launches a preemptive military strike without legislative authorisation – when it bypasses the very deliberative processes that are supposed to distinguish it from the authoritarian regimes it opposes – it undermines the moral foundation on which the entire theory rests.” It’s too early to know how the conflict will pan out, but he predicts it will fracture the Maga base even further.
His theory is that US history goes in 80-year cycles: “We have the Declaration of Independence; 80 years later, we have the civil war, to clean up the stain in the constitution related to slavery. We then have 80 more years. We go into the Great Depression, and then ultimately, because of the Great Depression, two catastrophic world wars, and we clean that up, we redeem ourselves. We have 80 years of peace and prosperity, but now we’re at that inflection point again.”
So in the long run, post-Trump, he is broadly optimistic: “I predict that we will go through a reflective period of time, a period of redemption and a period of renewal. That’s America. I believe that the country will heal itself, because the country always heals itself.”
