Bill Clinton once described Jeffrey Epstein as “both a highly successful financier and a committed philanthropist.” He provided “insights and generosity,” the former president told New York through a spokesperson in 2002, during a trip the two took aboard his private jet on a humanitarian tour of Africa that also included actors Chris Tucker and the now-disgraced Kevin Spacey. Clinton took several trips on Epstein’s private Boeing 727 jet, flight logs show. But after Epstein’s arrest on sex trafficking charges, the former president has drawn a line in the sand. “President Clinton knows nothing about the terrible crimes Jeffrey Epstein pleaded guilty to in Florida some years ago, or those with which he has been recently charged in New York,” a spokesperson said in a statement, downplaying Clinton’s interactions with Epstein and emphasizing that he was accompanied by staff and Secret Service on every leg of the trips.

These are anxious times for the rich, powerful figures who praised and hobnobbed with Epstein, who has pleaded not guilty, as well as officials like Labor Secretary Alexander Acosta, who enabled the financier’s alleged crimes. Epstein’s indictment Monday brought with it the possibility that other notable figures could be enveloped in the case, as the Miami Herald’s Julie K. Brown, whose reporting brought Epstein back into the spotlight, noted after his arrest. It also cast an unflattering light on his elite friends and associates, including the current president, who in that same New York magazine profile appeared to allude to Epstein’s proclivity for underage girls. “I’ve known Jeff for fifteen years. Terrific guy,” Donald Trump said 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.”

Trump, of course, is now doing his famous “I don’t know him” routine, despite his previous on-the-record comments. But Epstein was photographed at least twice with Trump at his Mar-a-Lago resort, in 1997 and 2000, and he had in his personal address book 14 phone numbers for Trump, Melania Trump, and their staffs, according to the Washington Post. (In his book Fire and Fury, journalist Michael Wolff reported that Trump and Epstein, along with private equity mogul Tom Barrack, were a “set of nightlife musketeers” together during the 1980s and ‘90s.) Trump was also directly accused of raping a 13-year-old at one of Epstein’s parties, but the 2016 lawsuit was later dropped; Trump vehemently denied the allegations as “categorically false” and “disgusting at the highest level and clearly framed to solicit media attention.” Other high profile figures have also been accused of abuse with Epstein, including Prince Andrew and famed attorney-turned-Trump defender Alan Dershowitz; each has denied the allegations.