In 2015, several years after his release from prison, Jeffrey Epstein showed up to a small lunch party at a Palm Beach mansion a few doors down from his own opulent estate, a neighborhood that is home to millionaires – and more than a few billionaires – like himself.
Several things stood out for one attendee who relayed this account to FOX Business. First, Epstein, a registered sex offender, easily mingled with the guests as if nothing in his past should concern them.
Also, Epstein, then in his early 60s, was accompanied by an extremely young woman whom he introduced as his girlfriend.
Then there were his shoes, or to be more exact, the obviously expensive pair of black-velvet slippers he was wearing. As the attendee remembered them, one slipper prominently featured a large ostentatiously embroidered image of a screw on its top. The other displayed a large embroidered letter “U.”
"We all got the message," the attendee said. "Jeffrey couldn't care less about what we thought about him or who he was with."
At least superficially, we know plenty about Jeffrey Epstein – his enormous wealth, his connections to Wall Street executives, politicians, his alleged predilection for soliciting minors that led to a brief jail term, and most recently, his death from an apparent suicide after being charged with operating a multi-state child sex-trafficking ring that could have put him away for the rest of his life.
But what we don’t really know is what inside Epstein’s brain made him think he could get away with his crimes and then, by some accounts, flaunting this lifestyle after he left prison in 2009. I've been asking that question a lot lately to people who knew Epstein over the years, did business with him and considered him a friend.
Their answers almost uniformly come down to the message on his slippers: Epstein's entire life and business career were a big "screw you" to doubters, detractors and just about anyone else.
This attitude certainly came in handy for much of his career on Wall Street. It helped the college dropout schmooze his way into a big Wall Street investment bank. And when he was ousted from that bank for running afoul of internal expense guidelines, it propelled him to a new career as a high-end money manager to billionaires and even become one (or at least close to one) himself.
Epstein's brashness – and willingness to spend money, of course – propelled him into the orbit of top academics and policymakers, who eagerly accepted his donations and his company. He loved to party, and he flaunted his wealth enough that it bought him friends like Prince Andrew, former president Bill Clinton and for a time, the current president, Donald Trump.
He also loved young women, and according to prosecutors, women that were too young, engaging in sexual acts with minors as if he would somehow escape legal scrutiny. Ultimately, he was wrong, of course, but Epstein, a decade earlier, managed to avoid serious jail time by fighting back. He hired a team of high-powered lawyers to raise questions about his accusers and craft a deal where he pleaded guilty to a single count of procuring a minor for prostitution and a single count of soliciting prostitution.
Epstein spent just 13 months in jail and was forced to register as a sex offender. But instead of leaving the country or keeping a low profile, he sought to re-establish his life of wealth and celebrity. He returned to the New York party circuit, explaining that he was not a pedophile, even if he had a thing for "teens and tweens." He told the New York Post in 2011, “I’m not a sexual predator, I’m an ‘offender.’ It’s the difference between a murderer and a person who steals a bagel.”
The braggadocio seemed to work for a while with his rich and powerful friends and business associates. Registered sex offenders aren’t exactly considered ideal neighbors for most of us, and yet after prison, he easily fit back into the Palm Beach social circuit and reconnected with top banks and brokerages.
As the media frenzy over his light sentence grew white-hot this year, Epstein seemingly brushed off the controversy as another hurdle to overcome. In March, he told me his experience being busted for "erotic massages" was not that much different than what happened to Robert Kraft, the owner of the New England Patriots, who earlier this year was also charged with soliciting prostitution.
The big difference, of course, is age: Kraft engaged in sexual acts with women of legal age, while Epstein was busted on sex charges involving underage girls.
Yet Epstein's biggest act of defiance may have been his return to the U.S. from France in early July – a country with weak extradition laws – only to be arrested on new child sex-trafficking charges that would have put him away for up to 45 years. As his former lawyer Alan Dershowitz told FOX Business at the time, Epstein's return is “mind-boggling ... [he] probably thinks he can beat the case.”
(Dershowitz would also pay a price for this association when he was accused in a lawsuit this year of having sex with one of Epstein’s alleged victims nearly 20 years ago. Dershowitz has denied the matter and says he has evidence to back up his innocence.)
Epstein's presence at that Palm Beach lunch party in 2015 wasn't quite mind-boggling, but there was a surreal aspect to it. As the attendee recalled, Epstein came uninvited; he lived just a few doors down and was just dropping by to say hello to the host – a wealthy entrepreneur – while taking a stroll in his swanky South Florida neighborhood.
Aside from the odd “screw you” slippers, Epstein was dressed casually in jeans and a zip-up shirt, also monogrammed with the letters “JE” on his chest. Epstein may be linked to some horrible crimes, but he wore that shirt like a badge of honor, the attendee thought.
As the attendee recalled, Epstein’s girlfriend was tall, thin and appeared young. She didn’t say much, but when she did, she spoke with what sounded like an Eastern European accent.
Epstein, for his part, was gregarious discussing various issues including the markets – since leaving jail he was back in business as a high-end money manager trading through some of the world's biggest banks – and the private island he owned in the Caribbean.
At one point, Epstein had struck up a conversation with a guest who owned a small private jet company. Epstein was particularly intrigued about the size of his jets and whether they were large enough to accommodate seating for all the people he would like to bring to the island during his next visit, the attendee recalled.
After about an hour, Epstein left to resume his stroll. Immediately, the gossip turned to the age of the girl. “Was she legal?” someone asked.
Then the conversation turned to Epstein's appearance.
“How about those shoes,” the attendee remarked to the party's host, who just shook his head and said, “that's Jeffrey."
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Again, in trying to answer how Epstein managed to return to his past life, I can’t help thinking of the message of his slippers. My belief is that Epstein’s bravado – the same sense of purpose that propelled him in business – helped him sell himself as a man who may have simply slipped up rather than a man who preyed upon underage girls. And like any good con, people bought it.
But even the best con artists eventually get caught – it's the law of averages (think Charles Ponzi or Bernie Madoff). After Epstein was arrested and was being housed in the federal lockup in downtown Manhattan, he again tried to game the system: Paying off prisoners, holding long sessions with his lawyers so he didn't have to spend so much time in his dank jail cell, according to the New York Post.
Yet there was, in this latest attempt to evade the judicial system, a futility to Epstein's best efforts: A judge denied him bail, meaning he couldn't return to his opulent mansion even while being monitored 24 hours a day. Friends abandoned him in droves and no bank wanted anything to do with him. The feds raided his residence and found photos of what "appear to be of underage girls, including at least one girl who, according to her counsel, was underage at the time the relevant photographs were taken,” prosecutors said, meaning he might have been hit with additional charges and a longer possible jail sentence if convicted.
That's probably the point when Epstein, finally devoid of his immense self-confidence, likely knew he couldn't get over on anyone anymore, which explains why a man so arrogant would kill himself.
FOX Business' Lydia Moynihan contributed to this story
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