Inside the rise, fall, rebound, and spectacular flameout of Anthony Scaramucci

NEW YORK CITY — There's something you need to know about Anthony Scaramucci: He's humiliated himself epically before but doesn't stay down.

Once upon a time, in the 1990s, he was fired from a job at Goldman Sachs, with a severance payment, only to be hired back to the elite investment bank within two months.

In 2010 he brought part of his business from Citigroup when the bank was basically on its knees. He took that and turned it into an annual "Davos in the desert," a must-attend Wall Street hedge-fund party in Las Vegas.

You see, he's done this several times. The latest version of it was a return to the Trump administration after he'd cast off and sent back to Wall Street with his head in his hands. That, of course, ended in a spectacular and public flameout after just 10 days as White House communications director.So it's only natural that people who know the man they call "The Mooch" are wondering, and speculating about, what the next move will look like.I can tell you a few things. First, the sale of his firm, SkyBridge Capital, looking to be priced at just under $200 million, is still happening. A person familiar with the deal says that it now could be a matter of days away.

I can also tell you that, for now, people close to Scaramucci say that he still sees a future for himself in politics, especially now that he thinks President Trump owes him a favor for his role in getting rid of former White House Chief of Staff Reince Priebus. This is obviously a gamble, but it's completely in character.

What follows is a story of a guy who made his way into the orbit of Donald Trump to gain a seat of power — and what that effort cost him before it imploded so quickly. In part it's a classic tale: Scrappy working-class kid makes it into the ranks of the 1% on Wall Street. But this kid, despite his financial success, is still maligned by some of the same money men who see him as an outsider who is more talk than substance. You could say most of America has the same impression right now. The story below is based on conversations with Scaramucci in months and years past, as well as with friends and colleagues as recently as this week. The Mooch himself did not respond to requests for comment for this story, though he did tell HuffPost this week just that he would "reemerge."

Make it legend

Here's The Mooch's origin story in 30 seconds. He's so practiced at telling it, he could probably give it to you in 20.

Anthony Scaramucci grew up on the North Shore of Long Island. His father worked construction, and he was the first in his family to attend an institution as venerable as Harvard Law School. As law school was ending — Mooch was class of 1989 — he considered Wall Street. At that time the industry was white hot and still on a 1980s "greed is good" high.

So Scaramucci interviewed at Goldman Sachs.

"I was wearing polyester everything," Scaramucci told me in 2012. "Black polyester suit, a thin black Guido tie, a white-on-white polyester shirt, if you know what that means, and narrow Capezio cockroach-killer shoes. My interviewer took me aside and told me, 'You are the worst-dressed kid I've met at this school.' I was mortified because I thought I looked fantastic!"

At the time he did not take his exams as seriously as he took his outfit. Instead of studying for the bar, Mooch spent the summer waterskiing on Long Island. Then there was the infamous Series 7 exam, a Wall Street stockbroker test. For that one, Mooch agreed to play "Series 7 Chicken." There was an $8,000 pot at stake for the person who could get the lowest score among his group of friends. Mooch won, partly because he was the only one who played.

Scaramucci did eventually make it into Goldman Sachs, but with an attitude like that, it wouldn't be long before he was fired. But again, here's the part of the story that remains relevant: He was back at the bank after two months."He is the way a lot of the guys brought up on Long Island in the '80s are," said Gregg Hymowitz, a former colleague, and the founder and managing member at Entrust Partners.

Entrust is a fund of funds business, like Scaramucci's SkyBridge. Hymowitz also passed through the three most influential institutions in Scaramucci's life around the same time — Long Island (the South Shore for Hymowitz), Harvard Law, and Goldman Sachs.

Long Island and its tough-guy, working-class culture sticks with you, Hymowitz said.

"This is the way you're brought up when you're middle class from Long Island. You go to Harvard, and those are still your roots. It's part of your story. You go to Wall Street and there's a mutual respect for people who pulled themselves up by their bootstraps."

It was Scaramucci who helped Hymowitz get into Goldman, but after an argument over a client, the two didn't speak for years. Hymowitz isn't 100% clear on what happened, but he doesn't remember ever getting that client. Back then, as now, The Mooch could be charming and generous one moment, aggressive the next.

SALT

Many of you likely won't be familiar with how Wall Street does a conference in Vegas, so allow me to describe it. The event, called SALT, is a very Scaramucci creation: four days of parties and discussions at the Bellagio Hotel.

Think pool time, political leaders, titans of international finance, live music from anyone including Lenny Kravitz and Maroon 5, parties, billionaires, millionaires, guys who run money, guys who wish they ran money, guys making deals, guys desperate to make deals, and lots of gambling. SALT stands for the SkyBridge Alternatives Conference. SkyBridge is Scaramucci's hedge fund of funds business — a firm he started after stints at Lehman Brothers and Goldman, and after selling his first hedge fund.

What SkyBridge does is pool investments from dentists and doctors, and it channels them into hedge funds that those not-wealthy-enough folks wouldn't be able to access themselves. Of course, they have to know about it. So making SALT as illustrious and newsworthy as possible was a focus of The Mooch's old life. In that life, Scaramucci was a married hedge-fund manager — with a fifth child on the way — who spent his days traveling the world talking about money — on CNBC, on Fox, on wherever and whatever would have him. In that life he had a TV show called "Wall Street Week"; he went to the world economic forum in Davos; he hung out with Caitlyn Jenner; and he donated to Democrats and Republicans.This year, at the event in May, Scaramucci's future was almost as uncertain as it is now, because, despite his efforts — including agreeing to sell SkyBridge — he'd been unable to secure a job inside the White House. He wasn't supposed to be there, a fact he acknowledged and which was a cloud hanging over the entire ceremony.

I'll give you an example.

So there he was interviewing William Ackman — a New York City billionaire on a mea culpa tour after losing a face-melting amount of money on a single bad bet in 2015 — when The Mooch addressed the question on everyone's mind. They were talking about Ackman's interest in investing in a certain fast-food chain.

"That's going to be my next job," The Mooch joked. "Flipping burgers at McDonald's."

The affable and self-deprecating tone was a signature of The Mooch, but he was addressing a question that the investors and fundraisers and journalists in attendance had been whispering about since last year's bash, when he'd informally announced that he would be shedding his old life and adopting a new one in the service of Donald J. Trump.He might have supporters, but Trump is not respected among this kind of Wall Street crowd. It's almost in the same way that the white shoes and blue blood of Wall Street wonder about the Mooch despite his financial success, except much, much worse. The idea of doing business with the Trump family is mostly anathema to them.

So the fact that Scaramucci — who spent his career trying to gain credibility in an industry heavy with legacies and snobbery — was attaching his brand to Trump's seemed like lunacy. But he had always been hungry for political clout, and he saw Trump as a fast track for someone like him, someone with no experience at all. He saw in Trump a way to enter the White House.

I asked him what he was doing almost immediately after he revealed that he would be joining team Trump through a series of supportive tweets in May 2016. It was the week before his Vegas party, and it was after he had supported Wisconsin Gov. Scott Walker and Florida Gov. Jeb Bush in their presidential bids earlier in the election.

Scaramucci explained that he had to go with Trump. On Bush's campaign, he was on "the last bus" behind Jeb's guys, Jeb's father's guys, and Jeb's brother's guys. On the Trump campaign, he was confident he could have a seat at the table. He would be in front. First bus.

Fame, American style

Anyone who knew The Mooch in those early days will tell you that he was always loved politics.

"He really identifies with the people that Trump proclaims to want to help. He's always been interested in politics and government," Hymowitz said.

By 2008 he was rich — so rich that he was featured on a CNBC special hosted by David Faber called "Untold Wealth."

"It makes me cringe when I say 'I am wealthy.' Then I think, 'What is the responsibility that comes with that?'" he said during an interview from his Long Island home. Shortly after, the camera cut to The Mooch walking by a massive golden harp in his sitting room. The special reported his net worth at about $85 million.

That's the money. The fame is harder to pinpoint if you're not from this town, but they are obviously intertwined. Scaramucci courted the press. Certainly not as aggressively as his recent ex-boss, Trump, who pretended to be his own publicist to leak stories. But The Mooch was known, at least to the financial press, and the city's two tabloids.

He was so known that when Bloomberg published the business proposal for his opulent Midtown restaurant, The Hunt and Fish Club, in 2013, the internet howled. " target="_blank"New Worst Place In Manhattan Coming Soon" heralded Gawker.

"At long last, the provincial burg of Manhattan will soon be home to an 'elite "clubhouse"' restaurant specifically for hedge fund guys. It will be called 'the entire borough of Manhattan.' Haha, a joke. No, it will be called hell," snarked Gawker writer Hamilton Nolan.

And like so many times in life, Wall Street whispered that the place with a "clubhouse feel" and attractive waitstaff (from the marketing documents) would never open. People knew that Scaramucci paid $100,000 for a SkyBridge cameo in "Wall Street 2." They knew his firm was small, and the way they saw it, he got more press than he had investing prowess.

You see, Scaramucci has never "run money," as they say on the Street. He's a marketing guy who funnels money into other people's funds and collects a fee for doing so. It's a slight, depending on the way you say it. Wall Street is a place that prides itself on being able to "eat what you kill."

Put another way: There was, and still is, an element of Wall Street that believed that The Mooch — with his CNBC appearances and his photos with famous friends — was all talk. They thought he lacked substance despite his success. SkyBridge, perhaps somewhat like the Trump Organization, was a cult of personality built on loyalty.

An orange sun

When Scaramucci is your surrogate, you can expect him to go out and box for you if you let him. As Politico reported, a few years ago, while interviewing PR firms, Scaramucci told one candidate, “I need someone who’s prepared to go to the mat and lie for me.”

And so once the men did join forces, dramatic things started happening. People who had been friends of Scaramucci's for decades started noticing a change. He was dazzled with Trump's wealth and his branded private jet in a way that seemed almost scripted out of a Hollywood movie.

Eventually, he would be hanging out at Trump Tower greeting people as they came to meet the president-elect in late 2016. Fox News' Charlie Gasparino called him "the millionaire doorman" on the air.

Questions about The Mooch's intentions were rising even before Gasparino's jab, and he started to turn away from his old life. It started in the summer of 2016. Suddenly no one knew what was happening with The Mooch's weekly business show on Fox, "Wall Street Week" — a show he fought hard to produce and distribute. There were rumors that he was angling for a post in the administration. There were rumors that he would sell SkyBridge, the firm he built with his hands.

Then the Scaramucci universe started whispering that he'd stopped speaking to friends he'd had for years.

It was around this time that a man named Arthur Schwartz moved into Scaramucci's inner circle. Schwartz is a publicist, and though he's gone as far as saying last week that he doesn't work for Scaramucci, he is known to journalists who've covered SkyBridge and The Mooch as Anthony's gatekeeper and, at times, attack dog.

By their nature, relationships like this are not totally clear. But Arthur plays the kind of rough-and-tumble politics that Scaramucci quickly became known for in his stint as communications director.

Schwartz, usually behind the scenes, rose to national attention with this tweet after when CNN's Jake Tapper demanded to know whether Scaramucci was aware that his assumed publicist was threatening the recently ousted White House chief of staff. It spiraled quickly, with Schwartz threatening legal action before backing down and deleting the tweets.

Selling SkyBridge

In the fall, The Mooch, itching to join team Trump in DC, started hunting for buyers for SkyBridge — down market, be damned. Eventually, he found them. Most of the firm — once the sale is complete — will belong to a Chinese conglomerate called HNA. We should note here that no one seems to be able to explain exactly who owns HNA, and recently the Chinese government has had a problem with that. Usually Wall Street does too.

That said, HNA is, according to several reports, paying multiples more for SkyBridge than the ailing firm is worth. Investors have pulled $1.6 billion from the firm over the past fiscal year and, again, the market.

Scaramucci explained that HNA was also willing to do the deal despite the fact that he was selling it to join the Trump administration, and with that he prepared for Washington. But a week after the inauguration, post after post was filled, and The Mooch's name was never called.

There was a stint when he went to the White House and tried to settle in. But according to reports, powerful elements (Steve Bannon and Reince Priebus) were angling to keep the wise-talking Long Islander doing a deal with the Chinese away from Trump.

At one point, things got so rough that Omarosa Manigault stole Scaramucci's office. It was said, up and down Wall Street, that he was coming back to New York City defeated.

And this was all before most of America even knew who The Mooch was.

Calling around

Pretty much all of Wall Street was shocked when The Mooch became White House communications director at the end of July. He looked and sounded familiar (he said "arbitrage spread" on TV), but he had a particular Trumpian glow about him.

He had won. And in that brief period, one longtime friend described The Mooch's victory like this, referring to his critics: "They think they're fencing, and he knows it's a knife fight."

But of course, the same person had a word of caution.

"I think anybody that's his friend has to worry about the Icarus complex — he can fly too close to the sun."

He did. When Scaramucci started on a Friday, he was giving charming, if not sycophantic, press conferences. Just over a week later, he was being escorted out of the White House. In the time between, in appearance after appearance, he had professed his undying loyalty to the president while stirring up new drama for the White House.

There was the time he said that Washington was a backstabbing town and that he didn't like that. "Where I grew up, we're front stabbers," he explained on national television.

There was the time he flipped out about leakers after Politico obtained his public financial disclosures during the regular business of reporting.

And there was the famous interview he gave to The New Yorker's Ryan Lizza: "What I want to do is I want to fucking kill all the leakers and I want to get the President’s agenda on track so we can succeed for the American people."

And: "I’m not Steve Bannon, I’m not trying to suck my own cock," he said, speaking of Trump’s chief strategist. "I'm not trying to build my own brand off the fucking strength of the President. I’m here to serve the country."

Scaramucci also threatened to fire the entire White House staff, which made people in his office uncomfortable, to say the least. America was not charmed. Even Fox News' Laura Ingraham chided The Mooch. The story entered the news cycle and wouldn't leave. The president had the spotlight taken from him.

Now it's unclear to anyone who has dealt with The Mooch why this happened. He knows how to deal with the press; he's been courting it for years. The Mooch we know on Wall Street doesn't drink or do drugs either.

Ex-SkyBridge employees will tell you that sometimes he feigned drinking at parties. Fake shots. The whole nine.

It could be, though, that he caught Trump disease. It happens if you get too deep in that family's orbit, it seems. Someone new starts hanging around Donald, and they think they can start acting like him. They become too familiar with power. They think they can get away with what he gets away with. But that's obviously not the case.

By the time Scaramucci was fired from the White House, the same elements that had brought him in (Ivanka and Jared, according to reports) were ushering him out. Those close to him say The Mooch's ambition was to become White House chief of staff once Priebus was out of the picture, but that job was given to Gen. John Kelly instead.

During all this drama, it leaked that his wife, Deidre, was divorcing him. He had been in West Virginia with Trump instead of in New York City for the birth of his child, just days after his first press conference. The tabloids said that she was sick of Trump.

To anyone who knows The Mooch, this is the weirdest part of the whole story. Not being around for the birth of his kid is just not like him. It is not like him to see his family, in this case his wife, talked about negatively in Page Six, New York City's most salacious social record, either.

One longtime friend and former business associate was offended, and told us Deidre was "smart, generous," and, in their view, "a caring mother to their son Nicholas."

Otherwise, old friends and employees say that everything else he's done — the loud talking, the blind loyalty — coincides with the most power-hungry and insecure parts of his personality.

"He always said he was focused on building SkyBridge, making the business the best it could be," said another person who's known him personally and professionally for years. "Many of his closest advisers challenged him on his motivations for that. But he doesn't realize how much he's fueled by the attention so he couldn't admit it ... to the point where he's sacrificed everything and seemingly almost everyone for it."