The Duke of York and Epstein are believed to have had a close friendship, partly exhibited by the infamous photo of the pair strolling through Central Park just five months after Epstein was released from jail for the solicitation of minors.
As well as his friendship with the convicted sex offender, Andrew is believed to have kept other unsavoury characters as companions.
In Tina Brown’s book, The Palace Papers: Inside the House of Windsor – the Truth and the Turmoil, she described how the prince had ties to gun smugglers, tyrants and foreign riff-raff.
An extract from the book, which is out later this month, reads: “International diplomacy rarely offers encounters with angels. But Prince Andrew’s adhesive contacts with reprehensible foreign riff-raff went far beyond what was explicable or acceptable.
“He hosted lunches at Buckingham Palace for the insalubrious relatives of Middle Eastern tyrants, invited a Libyan gun smuggler to Princess Eugenie’s wedding and Princess Beatrice’s 21st birthday party, and went goose-hunting with Kazakhstan’s then-president Nursultan Nazarbayev.”
The Duke’s character was also scrutinised by some of his acquaintances.
In 2019, the former Labour foreign secretary Jacqui Smith recalled on LBC radio that at a 2007 state banquet at Buckingham Palace for the Saudi king, she and her husband were left “slack-jawed” by the “awful jokes” Andrew made “involving camels”.
In the book, the royal author also described how Andrew had held a lunch with then-London Assembly chair Darren Johnson and then-London mayor Boris Johnson.
She said that Boris was so appalled by Andrew’s “inane pitch for city improvements”, he commented to the chairman on the way out: “I’m the last person to be a republican, but, f—, if I ever have to spend another lunch like that, I soon will be.”
But despite Andrew’s apparent shortcomings, his friendship is understood to have been useful to Jeffrey Epstein.
In the book, Ms Brown wrote: “Privately, Epstein told people that Andrew was an idiot, but – to him – a useful one. A senior royal, even if tainted, is always a potent magnet abroad.
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“Epstein confided to a friend that he used to fly the Duke of York to obscure foreign markets, where governments were obliged to receive him, and Epstein went along as HRH’s investment adviser. With Andrew as frontman, Epstein could negotiate deals with these (often) shady players.”
However, according to the writer, Andrew also benefited from his relationship with the shadowy financier.
She wrote: “Epstein always knew the right psychic buttons to press. There was a hollowness in the Duke’s personality. That’s why he laughed louder and boasted so much. He knew that for all the palaces he lived in and the servants who Sir’d him, he was the second son whose childhood parity with Charles was a mirage.”
She added: “Epstein deftly exploited Andrew’s sense of grievance. The wife of a financier who sat next to Andrew at an Epstein dinner told me how the Prince suddenly declared: “I don’t know why people don’t pay us royals more respect.
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“Epstein made Andrew feel he had joined the big time – the deals, the girls, the plane, the glittering New York world, where he wasn’t seen as a full-grown man still dependent on his mother’s Privy Purse strings or on the harsh pecking order of the Palace.”
The privacy of Epstein’s homes was also a valuable element to the pair’s relationship as it offered Andrew an escape from the “Palace censure” and “scorn from the press”.
In the book, Ms Brown writes: “On visits to New York, instead of staying as expected at the British consulate, Andrew stayed just five blocks away with Epstein so often, he was given his own grandly decorated guest suite. The sardonic Epstein christened it ‘the Britannica Suite”.”
Epstein’s house is also believed to have been regularly frequented by other high-flying individuals, with him being connected to people such as Donald Trump, Bill Clinton and Alan Dershowitz.
Ms Brown describes the “grotesquely vulgar and very weird decor” of the house which reportedly included “a life-size female doll hanging from a chandelier, a row of individually framed artificial eyeballs in the hallway, a portrait of Bill Clinton wearing Monica Lewinsky’s blue dress, and a huge chessboard with customised figurines modelled after suggestively attired members of his staff”.
Buckingham Palace were contacted for a comment.