Prince Andrew Ghislaine Maxwell
Prince Andrew and Ghislaine Maxwell are seen attending Royal Ascot in 2000.Tim Graham Photo Library via Getty Images
  • A documentary suggests that Prince Andrew may have dated a woman.

  • The Duke of York said that he had been introduced to a man named Jeffrey.

  • In the late '90s and early aughts, they were frequently seen together.

A documentary sheds light on Prince Andrew's relationship with a British woman who was sentenced to 20 years in prison for sex-trafficking children.

Buckingham Palace staff believed that Andrew and Maxwell dated at one point in the earlyaughts, according to two sources who were interviewed for the documentary.

In the early 2000s, Virginia Giuffre claimed that Prince Andrew had sex with her multiple times. Giuffre is currently suing Prince Andrew over allegations that he sexually assaults her at a number of places.

Prince Andrew said he didn't remember ever meeting Giuffre. After losing a bid to get Giuffre's case dismissed, the Duke of York was stripped of his royal patronages and military titles and told he would have to defend himself in the lawsuit as a private citizen.

There's still a lot we don't know about Prince Andrew's association with the convicted sex trafficker. Their friendship has been documented in news reports and interviews over time.

Prince Andrew met Maxwell when she was at university

In his interview with Newsnight, Prince Andrew said that he'd known Maxwell since she was a student.

During the time when the Duke of York was in the Royal Navy, he graduated from Oxford.

There is a well- connected family that comes from it. Her father was the owner of the Daily Mirror and a member of Parliament before he died.

The pair were often spotted together in the late 90's and early aughts

In the late 1990s and early 2000s, the friends were often pictured together, and their outings on the New York and London social scene were frequently covered in the press.

  • According to flight logs obtained by the Daily Mirror, Andrew and Maxwell traveled to Little St. James on a private jet.

  • A model who attended the getaway and later spoke to the Daily Mail said that Prince Andrew hosted the two men at his home.

A cache of images introduced at Ghislaine Maxwell's trial includes a photograph of her and Jeffrey Epstein relaxing at what appears to be Balmoral, Queen Elizabeth's royal residence in the Scottish highlands.US Attorney's Office for the Southern District of New York
  • According to a 2001 article in The Evening Standard, Andrew went to a fashion show in New York before going to Mar-a-Lago.

  • Andrew went to New York in April 2000 to socialize with Ghislaine.

  • The flight logs show Andrew flying on the private jet from New Jersey to Palm Beach, Florida, with another passenger.

  • The prince's 40th birthday was celebrated with a party at Windsor Castle.

  • There are two people pictured at the Royal Ascot.

  • The prince's former girlfriend, Aurelia Cecil, had a wedding in 2000. Two people arrive at a wedding in the same car.

  • There were two people pictured together at a Halloween party.

  • According to Andrew's interview with Newsnight, in December 2000 he hosted two people for a shooting weekend.

  • According to The Evening Standard, Andrew took a trip to Thailand with his friend.

They were thought to be dating at some point during this time. At the child-sex-trafficking trial last month, Cimberly Espinosa testified that she was the executive assistant to Maxwell. In the last two years of her employment at J. Epstein and Co., she got the impression that the two men were no longer together.

A former Buckingham Palace royal protection officer says Maxwell visited so often that he suspected she and Prince Andrew were dating

According to Paul Page, a former royal protection officer, Prince Andrew and Maxwell may have begun dating in 2001.

Buckingham Palace staff suspected Andrew and Maxwell had an "intimate relationship" because of the number of times she visited.

We suspected that she may have had an intimate relationship with Prince Andrew after she was allowed to enter and exit the palace at will. A colleague of mine remembers her coming in and out four times in a day.

One of the people who spoke on the program was Euan Rellie, who said he became friendly with Maxwell while he was a student.

According to the Telegraph, Rellie said in the documentary that Prince Andrew and Ghislaine had been dating in the past. They had a warm relationship.

The Prince Andrew's press office did not respond to Insider's request for comment.

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