Late monarch’s middle child has seen his reputation damaged over his friendship with paedophile Jeffrey Epstein and ties to alleged Chinese spy. Widely purported to have been the late Queen’s “favourite” child, Prince Andrew has suffered a sharp fall from grace over the last decade. Plagued by a string of controversies, the latest blow has seen new messages between the duke and Jeffrey Epstein come to light - sent months after Andrew claimed to have cut the disgraced financier off.

Emails between Andrew and Epstein handed to a court in London reportedly show they were still exchanging messages until at least late February 2011, when the duke wrote: “Keep in close touch and we’ll play some more soon.”. Andrew’s ties to the paedophile eventually forced him to step down from his royal duties and in January 2022, he was stripped of his royal patronages. In the years since, he has faced a number of other scandals, including a “close confidante” of his being banned from the UK over allegations he was a Chinese spy.

Here, The Independent takes a look at a timeline of Andrew’s fall from grace and his retreat from the public eye. The Queen stood by Andrew’s side even when he was caught up in the Jeffrey Epstein scandal in 2019 and “stepped back from royal duties for the foreseeable future”. In October 2021, it was claimed the monarch intended to spend millions of pounds privately funding her son’s defence against allegations of sexual abuse made by Epstein victim Virginia Giuffre.

She also signalled her support for her disgraced son by arriving alongside him for Prince Philip’s memorial service in March 2021. Andrew provided a steady arm for the Queen as she walked into Westminster Abbey to remember the life of her husband, just a few weeks after he reached a multimillion-pound out-of-court settlement with Ms Giuffre. During his 2019 interview with BBC Newsnight, Andrew said he had known British socialite Ghislaine Maxwell, the daughter of media magnate and former MP Robert Maxwell, since she was at university.

She introduced Andrew to her then-boyfriend Jeffrey Epstein in 1999. The trio enjoyed a close friendship, even after Epstein was convicted of procuring a child for prostitution and of soliciting a prostitute in 2008. Andrew is alleged to have personally invited the couple to Balmoral, the Queen’s Scottish residence, in 1999. Maxwell was sentenced to 20 years in prison in June 2022 following a New York sex-trafficking trial for procuring teen girls for Epstein for him to abuse.

Andrew continued to visit Epstein in New York after the financier’s conviction for child sex offences in 2008. Epstein received an 18-month sentence but was allowed to go on “work release” to his office most days and was released on probation after 13 months. Andrew faced criticism when pictures emerged of him opening the door of Epstein’s palatial East Side townhouse in December 2010 and the pair strolling through Central Park.

In his 2019 BBC interview, this is when royal claimed he had cut contact with Epstein. In 2019, Epstein accuser Virginia Giuffre, formerly known as Virginia Roberts, filed a lawsuit in Manhattan alleging she was trafficked by Epstein to have sex with Andrew on three occasions when she was 17 and a minor under US law. Ms Giuffre has accused Andrew of sexually abusing her on Epstein’s private island Little St James as a teenager, which the prince “unequivocally” denied.

Andrew was criticised for a car crash BBC Newsnight interview that aired on 16 November 2019. During the interview, he denied he slept with Ms Giuffre, saying an encounter could not have taken place because he was at a branch of Pizza Express in Woking with his daughter Princess Beatrice. He also said Ms Giuffre’s claim he was sweaty at a nightclub was untrue because an “overdose of adrenaline in the Falklands war” had left him unable to sweat.

The royal faced a public backlash, with equality campaigners claiming he was “too stupid to even pretend concern for Epstein’s victims”. Four days later, Andrew announced the Queen had given him permission to step back from public duties in the wake of the interview. He said it had become clear to him in recent days that his association with Epstein had become a “major distraction” to the royal family’s work.

The royal said he regretted his association with Epstein and “deeply sympathises” with his victims. In January 2022, the Queen stripped Andrew of his military titles and royal patronages in the wake of a US judge allowing Ms Giuffre’s civil sexual abuse case against her son to move to trial. The prince stopped using his HRH (His Royal Highness) style his roles – including Colonel of the Grenadier Guards, one of the oldest regiments in the British army – were handed to other members of the royal family.