Between Queen Elizabeth and Prince Philip's four children, Prince Andrew has perhaps experienced the most extreme highs and lows. Andrew is the subject of Andrew Lownie's 2025 book Entitled: The Rise and Fall of the House of York, which the BBC reported at the time as "an unrelentingly unflattering portrait" of the royal and "depicts him as arrogant, self-seeking and in denial about his links to the sex offender Jeffrey Epstein." While that was likely unwelcome news for the royal and his family, there's no denying that Andrew has made a few questionable decisions throughout his life. Those decisions have included continuing a long-term friendship with Epstein well after the latter's 2008 conviction on sex trafficking charges, as well as the alleged sexual assault of the late Virginia Guiffre. (Prince Andrew denied allegations she raped Guiffre, who died by suicide in April 2025, when she was underage. The pair settled a 2021 civil suit out of court for an undisclosed amount. The royal has maintained his innocence.) Keep scrolling to read more about Prince Andrew's ups and downs within the royal family. Sarah Ferguson Calls Ex Prince Andrew a 'Kind, Good Man' After Scandal His Place Within the Royal Family Prince Andrew Michael Brennan/Getty Images Andrew joined the royal family on February 19, 1960, as the first baby born to a sitting queen or king. By all accounts he had an upbringing typical to that of someone born into a monarchy. He eventually went to school at Scotland's Gordonstoun boarding school, which both his older brother King Charles and his father, Prince Philip, also attended. His Military Service Prince Andrew Keystone/Getty Images Andrew is a decorated military veteran and spent over 20 years in the British military. He expressed a desire to become a helicopter pilot as a child - a dream he realized after receiving his wings in 1981. Unlike most members of the royal family, Andrew saw combat during his time in the service. He flew several missions during the April 1982 invasion of the Falkland Islands by Argentina, and ultimately retired from the military in July 2001. His Marriage to Sarah Ferguson Prince Andrew Tom Stoddart/Getty Images Andrew and his ex-wife Sarah Ferguson married in July 1986, after having formed a friendship that went all the way back to childhood. The marriage was a celebrated one, and the pair quickly welcomed daughters Beatrice and Eugenie in 1988 and 1990, respectively. The couple announced their separation in 1992 and finalized their divorce in 1996. At the time, Ferguson's desire for a career outside of the royal family was said to have played a role in their decision to split. "I didn't want a divorce but had to because of circumstance. I wanted to work; it's not right for a princess of the royal house to be commercial, so Andrew and I decided to make the divorce official so I could go off and get a job," she later told Harper's Bazaar. It has since been reported that infidelity was also a factor in the pair's decision to split, and according to a report from the Daily Mail, Lownie's book claims Andrew would sometimes sleep with "more than 10 [women] a day." His Friendship with Jeffrey Epstein Prince Andrew Davidoff Studios/Getty Images Andrew's friendship with the late Epstein, who was arrested on federal charges of sex trafficking of minors and died by suicide in prison in 2019 while awaiting trial, came to light in 2010, when photographs of the pair in New York City surfaced. Epstein served just under 13 months in jail after pleading guilty to state charges of solicitation of prostitution and solicitation of prostitution from a minor in 2008. Royal watchers and the media were unwilling to let questions about the pair's relationship go, and in 2011 it was reported by several outlets that Andrew often spent time at two of Epstein's homes. Ferguson also once received a loan of $24,500 from Epstein, according to the same reports. Andrew was compelled to step down as trade envoy in 2011 as a result of the friendship and the subsequent scrutiny. His Sexual Assault Allegations Prince Andrew Chris Jackson/Getty Images A few years later, the late Guiffre accused Andrew of forcing her to have sex with him when she was underage. She claimed the acts took place at Epstein's private island in the Caribbean, as well as in New York and London. Though the palace initially denied the claims as "categorically untrue," Guiffre's accusations set off a firestorm of attention and scrutiny of which Andrew has not yet recovered. In 2019, he gave an interview to the BBC about his lengthy friendship with Epstein and Guiffre's allegations, and claimed he had "no memory" of taking a widely publicized photo with the then-teenager. His Changing Royal Duties Prince Andrew Max Mumby/Indigo/Getty Images The BBC interview did nothing to help Andrew, and he soon announced his decision to step back from royal duties. "It has become clear to me over the last few days that the circumstances relati