When Bill met Jeffrey: What was Clinton and Epstein's real relationship?

Sydney Morning Herald

25-07-2025

When Bill Clinton needed a plane for a whirlwind tour of Africa, his fixer knew the man to call.
In the autumn of 2002, the silver-haired former president with a megawatt smile was down on his luck and deep in debt.
Why not ask Jeffrey Epstein, the secretive financier known as a fixer for some of the richest people in the US, said Doug Band, Clinton's chief counsellor.
The nine-day trip the men then shared has now become a subject of intense focus for allies of the current occupant of the White House, who is struggling to shift the news agenda on from his own ties to the deceased paedophile whose 'little black book' contained 14 phone numbers for Donald Trump, and 21 for Clinton.
'Jeffrey is both a highly successful financier and a committed philanthropist ... I appreciate his insights and generosity during the recent trip to Africa.'
Bill Clinton, 2002
On Wednesday, a key Trump ally in Congress organised a successful vote to subpoena both Clinton and his wife, Hillary. Should they be deposed, they will be questioned once more about what they knew of the child sex-trafficking ring that was, at the very least, run right under the noses of the richest and most powerful people in the US.
'I'm never going to let this story go, because of what I heard from a source about Bill Clinton on a plane with Jeffrey Epstein,' said Dan Bongino, the deputy director of the FBI, shortly before he took office.
Clinton, now 78, has always denied having had any knowledge of the 'terrible crimes' committed by Epstein. 'I had always thought Epstein was odd but had no inkling of the crimes he was committing,' he wrote in his 2024 memoir, Citizen: My Life after the White House.
But there was enough strange behaviour on Epstein's luxury Boeing 727 jet for Band to claim he subsequently advised the former president to end their relationship.
On September 21, 2002, Clinton climbed on board, along with Kevin Spacey, Chris Tucker, Ghislaine Maxwell, and Epstein himself. Also present was a 21-year-old masseuse, Chauntae Davies, who later testified that she was repeatedly raped and abused by Epstein.
'The Lolita Express', as the aircraft would become known, had multiple private compartments and a 'Round Room' with a doughnut-shaped couch, according to its pilot. The cockpit door was always closed.
When not in the air, Clinton glad-handed with prime ministers and fellow presidents, beginning his relaunch as the kind of global statesman who could help to solve intractable problems such as the spread of HIV/Aids, and not an incorrigible Lothario who received oral sex from an intern in the Oval Office.
Providing the funds for this transformation – and basking in his proximity to power – was Epstein. It was a report on their trip in the New York Post's Page 6 that turned the shadowy fund manager into a figure of nationwide gossip, prompting two eyebrow-raising profiles in Vanity Fair and New York Magazine.
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Asked for his opinion of Epstein after the trip, the former president offered his gratitude but did not suggest the two were friends. 'Jeffrey is both a highly successful financier and a committed philanthropist,' he told New York Magazine.
'I especially appreciate his insights and generosity during the recent trip to Africa.'
Epstein, for his part, reportedly told friends that Clinton stunned foreign leaders in the same way Mike Tyson would if he walked into a downtown gym, saying: 'He's the world's greatest politician'.
There is no suggestion that Clinton was aware of how Epstein treated Davies, who was among dozens of young women known to hang around the bachelor. But it hurt his reputation when a photograph was released in 2020 of the young woman giving him a massage.
In the image, taken in a Portuguese airport en route to Africa, Davis stands behind the former president, kneading his shoulders.
'[Clinton's] stupid, but he's not an idiot,' one source told the reporters Daniel Halper and Alana Goodman, denying Clinton was engaged in sex with the young women who surrounded Epstein.
A clear rapport
But he was 'getting it on' with Maxwell, claimed the source, who was quoted in the journalists' 2020 book A Convenient Death: The Mysterious Demise of Jeffrey Epstein. A Clinton spokesman has called this claim 'a total lie'.
That the two had a rapport is clear. Another image from the Africa trip shows them standing side by side at the top of the stairs leading up to the cockpit, with Clinton's hand on Maxwell's shoulder.
On a stopover on the way back to the US, the former president joined in the cheeky tour Prince Andrew led around Buckingham Palace, in which Maxwell and Kevin Spacey were pictured sitting side-by-side in thrones reserved for the Queen and Duke of Edinburgh.
Even after Epstein's abuse was first uncovered, the pair remained in contact, with Maxwell invited to the wedding of Chelsea Clinton in 2010. By then, Epstein had finished his 13-month prison sentence for sexually abusing a minor, and Maxwell had been served with deposition papers in a separate civil suit.
On Thursday, Todd Blanche, the deputy attorney-general, was due to meet Maxwell, who is serving a 20-year sentence for procuring underage girls for Epstein to have sex with.
Democrats have warned that Blanche could float a full pardon for Maxwell in exchange for 'information that politically benefits President Trump'. Others have speculated she may be willing to stretch the truth in order to get out of prison.
In 2020, Band, Clinton's former fixer, gave what remains the most revealing interview about life on board Epstein's plane on that fateful Africa trip.
Epstein, he told Vanity Fair, made a series of ridiculous claims, including that he had invented the derivatives market. While unaware of Epstein's crimes, Band said he got enough bad vibes to advise a cease to all relations.
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The advice, apparently, was not immediately followed. Clinton has long denied ever having visited Little St James, Epstein's private island in the Caribbean, where much of his abuse took place.
But Band – who fell out with his former employer before the interview – claimed he did indeed visit, in January 2003, on a trip he declined to attend himself. A spokesman for the Clintons provided Vanity Fair with a detailed travelogue that contained no evidence of such a journey.
That Epstein got a kick out of his ties to Clinton was evident.
In his appeal against further sex-trafficking charges in 2019, Epstein's lawyers said he had been one of the originators of the idea for the Clinton Global Initiative, casting it as proof of his good intentions and, implicitly, of friends in high places.
A signed photograph of Clinton was displayed in his New York mansion and, later, Epstein bought a painting of the former president in red high heels and a blue dress – just like the one Monica Lewinsky reportedly wore for their Oval Office encounter.
Before it was ever hung on the wall, Clinton set some distance between himself and his rich acquaintance.
In late 2003, Epstein organised a dinner in honour of Clinton in New York. Also in attendance were Lord Mandelson and David Blaine, who performed card tricks to 'barely clad' models, New York Magazine reported. Clinton, however, never showed up.
And Trump's efforts to turn the focus onto his political rival are complicated by another name on the guest list that night – his own.