Errol at the Derby?🗡🏇

02 May

It’s been said by a credible source (but I have no written or photographic evidence) that Errol was at the 1956 Kentucky Derby, where he bet on aptly-named ‘King O’ Swords’, but witnessed “Needles’ win in one the greatest come-from-behind victories ever.

Anyone have any information or evidence of Errol being at this or any other Kentucky Derby?

Anyone see him in the photo below? :-)

— Tim


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  1. Selene Hutchison-Zuffi

    May 2, 2021 at 2:01 am

    I emailed Churchill down with no answer. I searched newspapers and I cannot find any mention of him. I am trying to find out where he was in May 1956…I think he was in spain

    • Gentleman Tim

      May 2, 2021 at 11:46 am

      Thank you, Selene. The exact date of the Derby in “56 was Saturday, May 5. Being the major horse racing enthusiast he was, I can’t imagine Errol never attending a Kentucky Derby. However, because of the huge crowds with numerous celebrities at Churchill Downs, I wouldn’t expect that his attendance would necessarily be big published news – especially not while he was on the downside of his career.

  2. Karl

    May 2, 2021 at 9:31 am

    Not much help but here are some time markers- at one point, only a puddle jumper away… maybe-

    Hollywood, California 5/6/56, “Rossanna Rory, Italian Actress, will be co-starred with Errol Flynn in ‘The Big Boodle”. The Melodrama will begin filming next week in Cuba. It is being produced independently by Lewis Blumberg and will be released by United Artists.’

    As reported in the New York Times, 6/17/56 and mentioned in the article “People and Pictures:

    ON LOCATION: “Add another production crew to the bustling Carribean scene. Last week, word from Havana had it that director Richard Wilson had taken his cast- Errol Flynn, Rosanna Rory, Pedro Armendariz, Gia Scala and Jacques Aubuchon- to Morro Castle for location scenes for “The Big Boodle”. Most of the adventure, adapted from the novel by Robert Sylvester, The New York Daily News columnist, is being filmed in the Cuban capital by producer Lewis Blumberg for United Artists.’

    He was in Spain, as you may recall, by the fall:

    On 9/23/56, in the UP article “Errol Flynn Has Surgery” ‘…
    The reports said Mr. Flynn arrived Thursday at Ibizia… aboard his yacht Zaca…

    • Gentleman Tim

      May 2, 2021 at 11:51 am

      Great info, Karl! Thank you!

      In light of these markers you provide, perhaps the King of Swashbucklers went to bet on the King O’ Swords en route to Cuba, and/or as a side trip from New York.

      • Selene Hutchison-Zuffi

        May 2, 2021 at 11:54 am

        I found an article stating that his wife Pat was in London and that Errol might have been in London right before leaving for Cuba. If he was in London then then doubt he went to KY then Cuba. Churchill Down won’t reply. They would have that info unless he went in incognito

        • Gentleman Tim

          May 2, 2021 at 4:02 pm

          Good info, Selene. I certainly wouldn’t put it past Errol Flynn to go to the Derby before showing up in Havana for filming that started a week or so later. …Did Churchill Downs keep records of all celebrities who showed up for the Derby? I wouldn’t think so. Moreover, Errol may not have advertised his attendance for numerous reasons, including perhaps to avoids service of summons and/or because the IRS may have been was watching him closely at that time and wouldn’t be thrilled that he was betting and partying in Louisville with money due the Taxman.

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