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Timeline: the Duke of York's questionable friends
Prince Andrew, the Duke of York, has been linked with various unsavoury characters over the last several years.
2000: Invites Jeffrey Epstein to Sandringham together with close friend Ghislaine Maxwell. Epstein is later convicted of child sex offences while Miss Maxwell is said to have "procured" girls for him.
June 2007: Introduces socialite Goga Ashkenazi to the Queen as he spends the day with her in the royal box at Ascot racecourse. Miss Ashkenazi, the mistress of the Kazakh billionaire Timur Kulibayev, is later rumoured to have helped him find a buyer for his house, Sunninghill Park.
September 2007: Sells Sunninghill Park, his home in Berkshire, to Mr Kulibayev for £3 million more than the £12 million asking price, despite no other offers being made.
November 2007: Meets Col Gaddafi's son Saif al-Islam for the first time. He is reported to have had at least four further meetings with the Libyan, though Buckingham Palace insists he has only met him twice.
November 2008: Enjoys four-day holiday in Tunisia paid for by Tarek Kaituni, a convicted Libyan gun smuggler, before visiting Col Gaddafi in Libya.
October 2010: Hosts a business lunch at Buckingham Palace for Sakher el-Materi, the son-in-law of the now deposed Tunisian president Zine al-Abidine Ben Ali. Mr el-Materi is under investigation for money laundering.
December 2010: Meets Jeffrey Epstein, now a convicted paedophile, in New York, where the two men are pictured in conversation as they stroll through Central Park.
Feb 28, 2011: David Cameron faces calls in Parliament to strip the Duke of his role as trade ambassador over his friendships with Saif Gaddafi and Tarek Kaituni.