- Winner claimed during his lifetime to be worth £75 million, with £25m in offshore bank accounts and his home worth an additional £50m. But on his death his bank accounts were frozen, and a formal investigation of his affairs began. During this, it emerged that Winner had been supporting two former lovers, both of whom had been provided with living expenses and accommodation. The financial assistance extended also to his long-term personal assistant, the former Miss Great Britain Dinah May. After investigations, it was revealed that Winner's total estate was actually worth £16.8m, with total outstanding debts of £12m. In his will, Winner had left his wife a lump sum of £5m, but the residual estate was only worth £4.75m. His former wife, P.A. and lovers engaged probate lawyers to contest the will and their sums due from it. However, it then emerged that none of the newspapers that reported the aforementioned information about Michael's beneficiaries were correct and that they included only probate information from UK assets when Michael Winner was on record as stating that he had substantial assets in Guernsey. When Guernsey probate was later added, Michael had left a total of £50m and this was more than enough to provide for all his beneficiaries in full while leaving a substantial balance to the Police Memorial Trust.
- Tended to get his films done on time and under budget.
- He persuaded Oliver Reed to audition for a part in Gladiator (2000), which turned out to be his final film.
- He was offered the opportunity to direct The Prime of Miss Jean Brodie (1969), The French Connection (1971), Jaws (1975), King Kong (1976) and a James Bond film, all of which he turned down.
- In September 2011, Winner was admitted to hospital with food poisoning after eating steak tartare, a raw meat dish, four days in a row. The dish is not recommended for those with a weak immune system and in retrospect Winner regarded his decision to eat it as "stupid".
- Often edited his own films under a different name 'Arnold Crust'.
- He allegedly declined the O.B.E. (Officer of the Order of the British Empire) in 2006 for his services to film.
- His favorite actor was Marlon Brando, who was also a friend.
- He was going to be interviewed for the documentary Electric Boogaloo: The Wild, Untold Story of Cannon Films (2014), but died while the film was in production.
- In an interview towards the end of his life, he cited not having children as his regret in life.
- An outspoken supporter of the Conservatives for many years, he switched his political allegiance to Tony Blair's Labour Party in the 1997 UK General Election.
- In Dec. 2006, while vacationing at Barbados, he suffered a near-fatal illness from the extremely rare vibrio vulnificus virus, caught when he ate an oyster. After spending 5 days at the local hospital, his friend Philip Green chartered an ambulance plane to fly the director to London. He spent 3 months in the hospital where he ultimately went through 19 operations to save his leg. The virus destroyed his Achilles tendon and he had to walk with a walking stick.
- At one time, he was going to direct Delta Force 2: The Colombian Connection (1990), but star Chuck Norris didn't like the script.
- In 2003, he appeared in a series of adverts for a UK car insurance firm while dressed as a fairy godmother.
- Winner was an active proponent of law enforcement issues and established the Police Memorial Trust after WPC Yvonne Fletcher was murdered in 1984. Thirty-six local memorials honouring police officers who died in the line of duty have been erected since 1985, beginning with Fletcher's in St. James's Square, London. The National Police Memorial, opposite St. James's Park at the junction of Horse Guards Road and The Mall, was also unveiled by Queen Elizabeth II on 26 April 2005.
- Following the allegations made against Harvey Weinstein in October 2017, Winner was accused by three women, Debbie Arnold, Cindy Marshall-Day and an unidentified woman, of demanding they expose their breasts to him, in Arnold's case during an audition at his home. The two named women refused.
- In an interview with The Times newspaper in October 2012, Winner said liver specialists had told him that he had between 18 months and two years to live. He said he had researched assisted suicide offered at the Dignitas clinic in Switzerland, but found the bureaucracy of the process off-putting.
- Winner spent his free time gardening ("my garden is floodlit, so I quite often garden after midnight") or with a string of girlfriends, notably the actress Jenny Seagrove.
- He was a restaurant critic and guested in a television commercial for Kenko instant coffee in which he was spoofing himself.
- January 2008 - Engaged to Géraldine Lynton (aka Geraldine Lynton-Edwards).
- He was a regular panellist on BBC Radio 4's Any Questions and later appeared on television programmes including the BBC TV's Question Time (1979) and Have I Got News for You (1990).
- Was going to direct Captain America (1990) for Cannon Films. A script was written by himself and Stan Hey, but original creator Stan Lee read the script and hated it, and the project eventually fell through.
- He featured in TV commercials that he himself directed for insurance company esure between 2002 and 2009, with his trade-mark catchphrase "Calm down, dear! It's just a commercial!".
- His fame as a restaurant critic was such that, at a Cornwall cafe, an unconsumed piece of his serving of lemon drizzle cake was incorporated into the Museum of Celebrity Leftovers.
- Directed Harry Andrews in five films and James Donald in three feature films.
- He openly claimed after he retired from film directing that he never once worked with a temperamental or difficult leading actor.
- Winner lived in the former home of painter Luke Fildes in Holland Park, Woodland House, designed for Fildes by Richard Norman Shaw. It was announced in 2008 that Winner intended to leave his house as a museum, but discussions with Kensington and Chelsea council apparently stalled after they were unable to meet the £15 million cost of purchasing the freehold of the property, which expires in 2046.
- He was considered to direct The Wild Geese (1978).
- Winner was an art collector, and a connoisseur of British illustration. Winner's art collection includes works by Jan Micker, William James, Edmund Dulac, E. H. Shepard, Arthur Rackham, Kay Nielsen and Beatrix Potter. His collection once included almost 200 signed colour-washed illustrations by Donald McGill.
- He was embarrassed by The Cool Mikado (1963), which he dismissed as "absolute nonsense, shot in four weeks on the silent stage in Shepperton".
- It was announced that he was to direct Oliver Reed in a biopic of William the Conqueror, but the project never materialised.
- Was a close acquaintance of John Cleese, having lived in the same street as him for several years.
- Debbie Arnold publicly spoke of Michael Winner asking her to 'expose her breasts' during audition, other actors have come forward such as actress Cindy Marshall-Day as well as others. While these accusations cannot be followed through with since Winner's passing it is part of his legacy as the truth of the kind of man he was.
- Employs Dinah May and Joanna Kanska as receptionists.
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