By Dayo Ade Olusola | 7 August 2025
When Bill Clinton peered out the window of a private jet as it descended over Africa in 2002, he may not have realized how much the trip would come to define his post-presidency
The journey was pitched as a humanitarian mission — part of his new AIDS initiative — covering five African nations and including a meeting with former South African president Nelson Mandela.
But over time, the core mission of that trip has been overshadowed. Clinton was not flying solo: he was joined by actor Kevin Spacey, comedian Chris Tucker, and their now-notorious host — convicted sex offender Jeffrey Epstein.
The flight was aboard Epstein’s private Boeing 727, later nicknamed “The Lolita Express,” a jet that became symbolic of the disgraced financier’s twisted empire of wealth, influence, and abuse.
Kevin Spacey later told Piers Morgan in an interview that he found Epstein’s entourage unsettling. “There were young girls on those flights. I didn’t understand at the time who they were or why they were there,” he said. “I felt Epstein put the President at risk with those young girls on board.”
A now-infamous photo from the trip shows a relaxed Clinton, 56 at the time, seated in a lounge chair as Chauntae Davies — then a 22-year-old massage therapist employed by Epstein — rubs his shoulders.
This week, both Clinton and former U.S. Secretary of State Hillary Clinton were subpoenaed by the House Oversight Committee as part of an expanding investigation into Epstein’s network and possible links to high-ranking officials.
The Committee’s letter to Hillary Clinton referenced a “close relationship” between the Clintons and Epstein, as well as his longtime associate Ghislaine Maxwell, according to reports.
Clinton’s connection to Epstein wasn’t forged on that 2002 flight — it stretched back at least a decade.
Records show Epstein donated $1,000 to Clinton’s 1992 presidential campaign and contributed $20,000 to Hillary Clinton’s Senate bid in 1999.
Between those donations, Epstein and Maxwell reportedly visited the White House 17 times during Clinton’s two-term presidency, starting in 1993.
In 2002, Epstein was also said to have visited Clinton at his post-presidency Harlem office, located inside the Clinton Foundation headquarters.
That Africa tour was reportedly Clinton’s second of what flight logs suggest were at least 26 journeys aboard the “Lolita Express.” On some occasions, he is believed to have flown without Secret Service protection — a breach of standard security protocols.
Bill Clinton with his arm around Chauntae Davies in another photo from the archive.MEGA
Now, lawmakers are combing through those journeys again amid renewed interest in Epstein’s powerful web of connections. The move follows revelations that Maxwell, currently serving a 20-year sentence, has supplied her lawyers with a list of 100 names allegedly linked to Epstein.
Following that 2002 trip, Clinton’s former aide Doug Band told Vanity Fair that he had long urged the ex-president to steer clear of Epstein, but those warnings fell on deaf ears.
Band also claimed Clinton visited Epstein’s private Caribbean island, Little St. James — dubbed “Pedophile Island” by locals — in early 2003.
Clinton has denied ever setting foot on the island. But one of Epstein’s most prominent accusers, Virginia Giuffre (formerly Roberts), wrote in a court filing that she saw Clinton dining there with “two lovely girls.”
Giuffre, who also alleged she was trafficked to Prince Andrew, made the claim in a fictionalized memoir included in her 2015 defamation lawsuit against Maxwell.
She described Clinton as “teasing the girls on either side of him with playful pokes and brassy comments,” adding, “There was no modesty between any of them.”
The manuscript, titled The Billionaire’s Playboy Club, was never published but has been submitted in court proceedings.
In the years that followed, Clinton consistently sought to distance himself from Epstein. His team maintains that he severed ties with the financier long before his 2007 and 2019 arrests.
In a 2019 statement, a Clinton spokesman said the former president “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.”
Requests for comment from Clinton’s office this week have gone unanswered. He has not been accused of any criminal conduct in connection with Epstein or his victims.
Spencer Kuvin, a Florida lawyer who represented Epstein’s earliest accusers in 2007, said that while Clinton’s name came up during his investigations, he found no evidence of direct wrongdoing.
“There was a pattern of socializing,” Kuvin said of Clinton and Epstein. “He [Epstein] wanted to befriend as many high-profile people as possible. If they were stuck on a plane with him for hours, he had their attention.”
Though Clinton sought to downplay the relationship, Epstein appeared keen to flaunt it. A journalist who met Epstein shortly before his 2019 death noted a framed photo of him with Clinton displayed prominently in his home.
Following Epstein’s death, FBI agents found a provocative painting in his Manhattan townhouse: an image of Bill Clinton in a blue dress — reminiscent of the one worn by Monica Lewinsky — lounging on a chair.
And while Bill has distanced himself, Epstein’s ties to the Clinton family endured. In 2010, Ghislaine Maxwell was among the guests at Chelsea Clinton’s wedding.
