Prince Andrew has been under pressure for a long time over his association with paedophile financier Jeffrey Epstein and his sex trafficker girlfriend Ghislaine Maxwell.

Here is how that friendship led to the prince’s disgrace and downfall.

– 1990s

Andrew previously told BBC Newsnight he first met Epstein through “his girlfriend back in 1999”.

In March 2011, the prince’s then-private secretary Alastair Watson, who spent nine years in the role, wrote to The Times newspaper saying Andrew met Epstein in the “early 1990s”.

Andrew later said he saw Epstein “infrequently”, adding “probably no more than only once or twice a year”.

During Maxwell’s sex trafficking trial, jurors hear Andrew flew on Epstein’s private plane with a 14-year-old girl in the mid 1990s.

– 2000

Andrew and Maxwell are seen on holiday with Epstein at Donald Trump’s Mar-a-Lago club in Palm Beach, Florida.

Epstein and Maxwell attend a party at Windsor Castle hosted by Queen Elizabeth II to mark Andrew’s 40th birthday, the Princess Royal’s 50th, the Queen Mother’s 100th and Princess Margaret’s 70th.

Flight records from May show him confirmed as a passenger on Epstein’s private plane.

– 2001

Virginia Giuffre claims to have had sex with Andrew “three times, including one orgy”, with the first encounter allegedly taking place in Maxwell’s London townhouse.

Ms Giuffre also claimed to have had sex with Andrew at Epstein’s New York flat and at an “orgy” on his private island Little St James in the Caribbean.

Read More: How links to sex offender Jeffrey Epstein led to Prince Andrew’s downfall