Sixty-six years ago today, John Wayne unveiled the most expensive gamble of his career. The Alamo premiered on October 24, 1960, after the Hollywood legend mortgaged property and borrowed against personal assets to finance a Western that would cost approximately $12 million. Despite seven Oscar nominations, the movie ultimately won just one.

Wayne had spent years trying to bring the Battle of the Alamo to the screen. But the movie that became his directorial debut also exposed the financial risks of making a Hollywood epic on his own terms.

Next: 50 Years Ago Today: John Wayne Said Goodbye in a Movie Later Named One of the ‘Greatest Westerns’ Ever

John Wayne Risked His Fortune on ‘The Alamo’

According to the Texas State Historical Association , the production’s original $7.5 million budget ballooned to approximately $12 million. Wayne mortgaged his houses and secured loans against his automobiles and yacht.

The American Film Institute documents an even higher contemporary estimate.…