NEW YORK - He has rubbed elbows with a prince and flown a former president on his private jet. He amassed a fortune that includes a 100-acre island in the Caribbean and one of the biggest mansions in New York.
He has donated tens of millions of dollars to Harvard and other causes, becoming a darling of professors and scientists — all without a college degree.
Jeffrey Epstein has long been an enigma, his ascent shrouded in mystery. Just how a middle-class Brooklyn math whiz became a Wall Street master of high finance with friends in very high places has been a subject of tabloid speculation for years.
Now, the details of Epstein's life and his alleged predilections are coming into sharper focus as federal prosecutors in New York pursue sex-trafficking charges accusing the 66-year-old billionaire of recruiting and abusing dozens of underage girls at his mansions in New York and Palm Beach, Florida, in the early 2000s.
Epstein, who pleaded not guilty Monday, could get up to 45 years in prison if convicted.
The financier avoided a potentially long prison sentence on nearly identical allegations more than a decade ago thanks to a once-secret agreement with federal prosecutors in Florida that has been widely criticized as a sweetheart deal.
In bringing charges this time, prosecutors in New York said a search of Epstein's Upper East Side mansion over the weekend yielded a vast trove of hundreds or even thousands of lewd photos of young women or girls.
Epstein's defence attorneys contend he never used violence or coerced any of the girls, and that his actions amount, at most, to soliciting prostitution. They say the charges should be dismissed in light of Epstein's earlier plea deal.
"This is ancient stuff," defence attorney Reid Weingarten said during a court appearance Monday.
Epstein has long obscured the source of his wealth. Even after his arrest, he refused to provide authorities with even basic information about his income and assets. His attorney said Epstein's lawyers intend to provide the information but want to make sure it is correct first.
This much is clear: "He is a man of nearly infinite means," federal prosecutor Alex Rossmiller said in court.
The somewhat reclusive Epstein splashed onto the international scene in 2002 after a New York tabloid reported he had lent his Boeing 727 to ferry former President Bill Clinton and other notables on an AIDS relief mission to Africa.
Profiles in New York magazine and Vanity Fair followed, establishing Epstein's reputation as an exorbitantly wealthy playboy and a stealthy Wall Street mover and shaker. Vanity Fair in 2003 described him holding court in his extravagant New York mansion with real estate tycoons, business executives and the scions of some of America's wealthiest families.
He was said to spend 75 minutes a day practicing yoga with a personal instructor and eschewed email for face-to-face conversations. Vanity Fair reported that he drank Earl Grey tea and didn't touch alcohol, tobacco or drugs.
Epstein also enjoyed surrounding himself with women much younger than him, including Russian models who attended his cocktail parties and beautiful women he flew aboard his plane, according to the Vanity Fair profile.
His friends over the years have included Donald Trump, Britain's Prince Andrew and former Harvard law professor Alan Dershowitz.
"I've known Jeff for fifteen years. Terrific guy," Trump told New York magazine in 2002. "He's a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side. No doubt about it — Jeffrey enjoys his social life."
The writer of the Vanity Fair article, Vicky Ward, said Monday that she had also interviewed two girls who alleged Epstein tried to entice them into sexual activity, but that the magazine didn't run that part of story. Former editor Graydon Carter said it was cut because he "didn't have confidence" in Ward's reporting.
Epstein grew up in the Coney Island neighbourhood of Brooklyn, the son of a New York City parks department employee.
He taught calculus and physics at the prestigious Dalton School, a prep school in Manhattan, from 1973 to 1975, despite not having a college degree. Attorney General William Barr's father, Donald Barr, was headmaster at the time.
Dalton graduate Paul Grossman said that he never had Epstein in class but that he was known among students as a math whiz.
"Everyone pretty much knew him as brilliant," said Grossman, who graduated in 1978. "None of us were surprised that when he left Dalton he made a zillion dollars in business."
William Barr has decided not to recuse himself from overseeing Epstein's case, a Justice Department official told The Associated Press on Tuesday. But Barr has withdrawn from taking part in any review of the 2008 deal in Florida because Barr's former law firm previously represented Epstein, the official said. The official was not authorized to discuss the matter publicly and spoke on condition of anonymity.
Epstein left Dalton in the mid-1970s for a job at Bear Stearns at the urging of a student's father who arranged a meeting with the chairman of the investment bank, according to published reports. He later began his own money-management business, J. Epstein & Co.
Epstein also forged a relationship with Leslie Wexner, the retail titan behind Victoria's Secret, The Limited and other store chains. He started managing Wexner's money in the late 1980s and helped straighten out the finances for a real estate development Wexner was backing in a wealthy Columbus, Ohio, suburb.
It was through Wexner that Epstein acquired his Manhattan mansion, a seven-story, 21,000-square-foot former prep school less than a block from Central Park. It has been valued at about $77 million.
Wexner's relationship with Epstein soured around the time of the money man's Florida arrest, and Wexner severed ties with him nearly 12 years ago. Wexner has not commented on Epstein's latest arrest.
"Little is known or said about Epstein's business except this: He manages money for the extremely wealthy," the Palm Beach Post reported in 2006 after Epstein's legal troubles began there. "He is said to handle accounts only of $1 billion or greater."
In 2008, he reached a non-prosecution agreement with federal prosecutors in Florida over allegations of sex with underage girls. He was allowed to plead guilty to state charges of soliciting a minor for prostitution and served 13 months in jail. The deal also required that he reach financial settlements with dozens of his alleged victims.
Epstein nearly got another break in 2011, when the Manhattan District Attorney's office took the unusual step of asking a judge to register him as a lowest level sex offender so he wouldn't be required to check in with authorities every 90 days. Judge Ruth Pickholz balked, saying she had "never seen a prosecutor's office do anything like this," and the DA's office later reversed its position.
Federal prosecutors acknowledged Monday that the current charges overlap with the Florida case from more than a decade ago. But they said one count in the indictment is based entirely on New York victims.
Epstein spent most of his time in recent years in the Virgin Islands and regularly flew off to foreign destinations, making more than 20 trips in and out of the U.S. on his private jet in the last 18 months, according to prosecutors. He has six homes, including one in Paris, and two private planes.
Workers in Epstein's New York neighbourhood said Tuesday that they rarely saw him, if at all, in recent years.
A bellman a few doors down who declined to give his name said he saw the billionaire leaving his mansion about three months ago with a woman who was covering her face. The bellman said he had seen multiple women going in and out maybe once every two weeks.
Michelle Licata, who says she had sexual encounters with Epstein when she was 16, welcomed his arrest .
"The first moment of finding out that Jeffrey Epstein was put in jail was so relieving to me I felt safer," she said Tuesday on ABC's "Good Morning America." "I've waited for this one day just to happen and it's finally come."
Associated Press writers Ali Swenson, Bernard Condon and Randy Herschaft in New York, Michael Balsamo in Washington, Danica Coto in St. Thomas, Virgin Islands, and Curt Anderson in Fort Lauderdale, Florida, contributed to this report.