The Tasmanian and the Revolutionary: Swashbuckling Errol Flynn and Fidèl Castro

Toward the end of his debauched life, fading Tasmanian-born Hollywood star Errol Flynn spurned the swords and the green tights, grabbed his Royal portable typewriter and headed for Havana for Hearst Newspapers.

He arrived in Cuba with photographer Bill Crespinell just as Fidèl Castro’s rebels were preparing to sweep down from the Sierra Maestra to topple the corrupt Batista dictatorship. “He was in the fighting zone as a kind of war correspondent,” Castro later told the Los Angeles Times. Flynn's stated rationale? "Ever since boyhood I have been drawn, perhaps romantically, to the ideas of causes, crusades. I wanted to see what makes an idealist tick." And his finding? "Anyone with intelligence is a Communist at 20, anyone who's a Communist at 40 is a fool." But was the real reason an attempt to butter up to Castro to save his investment in a Havana movie theatre, post-revolution?

Flynn stands beside Che Guevara listening to Castro in Sierra Maestra

Flynn wrote features headlined "Me and Castro" and "I fought with Castro" for the New York Journal-American after a mere five days, from Christmas Day 1958, in the mountains with Castro. "I feel that the citizens will know who you are ... and it will cheer them to know that someone from the United States, whom they perhaps have seen on the screen, is interested enough to come and see them," Castro told him. In return Flynn gave Castro lessons in public speaking.  

Flynn stayed long enough to see Castro sworn in as Cuban president in February 1959. Back in the US, he appeared on CBC’s Front Page Challenge and naively defended Castro. Nonetheless, his documentary, The Cuban Story, which played once in Moscow and was then lost until a print turned up in 2004, has become one of the key accounts of Castro's revolution. Flynn died in Vancouver, aged 50, on October 14, 1959.