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Inside Prince Andrew and Jeffrey Epstein’s controversial 20-year friendship

Prince Andrew's relationship with convicted sex offender Jeffrey Epstein came under renewed scrutiny in June 2019 as investigators pursued new trafficking and conspiracy charges against the disgraced financier.

The Daily Mail surfaced footage of the Duke of York at Epstein's Manhattan home reportedly filmed in December 2010, after Epstein had faced jail time for underage prostitution charges and registered as a sex offender.

The footage is the latest in the nearly 20 years of documented contact between Andrew and Epstein, a time identified to have overlapped with when prosecutors said Epstein recruited and abused underage girls.

The Duke's name was in Epstein's “Little Black Book” and on flight logs for the financier's plane. Buckingham Palace has never denied a friendship between Epstein and Andrew but has repeatedly denied that the prince had sexual relations with any underage girls.

On August 24, Prince Andrew released a statement through Buckingham Palace that said he met Epstein in 1999 and saw him “infrequently and probably no more than only once or twice a year,” including after his 2010 release from prison. The Duke of York called it “a mistake and an error” to see Epstein after his first conviction of soliciting minors for prostitution.

Andrew also said in the statement that he stayed in “a number” of Epstein's residences, but that he did not “see witness, or suspect” any of the criminal behavior that led to his June 2019 indictment.

In a widely panned November 16 interview with the BBC, the Duke made several elaborate claims in an attempt to discredit the allegations by a woman who has claimed he kept her as a “sex slave,” but the interview sparked incredulous responses and did very little to quell concerns over the allegations.

Some experts and lawyers have urged Andrew to get involved with the FBI inquiry into Epstein, but he did not appear to be planning to offer information on his late friend.

Here's a look at the pair's connections through the years.