Starting in the silent era of the 1920s and stretching to the late \u201870s, John Wayne seemed synonymous with film stardom and success. However, there was one point in his career that Wayne actually went broke, right in the midst of all that fame. At that point, he had been a little over 25 years in the entertainment industry, meaning this was not the premature flash and sizzle-out of a newcomer making rookie mistakes. Instead, it came down to poor financial decisions by both Wayne and his manager. John Wayne goes almost completely broke after decades in the industry Well into his career, John Wayne almost went completely broke \/ Everett Collection Wayne reflected on the path to going broke, outlining, \u201cI suddenly found out after 25 years that I was starting out all over again.\u201d He further admitted. \u201cI just didn\u2019t have it made at all. Until last year I had a business manager who didn\u2019t do anything illegal, but we were involved in many unfortunate money-losing deals. I would just about break even if I sold everything right now.\u201d RELATED: The Reason John Wayne And Clint Eastwood Never Acted Together Part of those poor choices included taking a big risk on himself as a director. 1960 saw the premiere of The Alamo, the passion project Wayne wanted to do because it would be based around the Battle of the Alamo. So, Wayne invested $1.2 million into making this film, pooling it with contributions from friends. Things would then go wrong in unanticipated ways. Profits and losses 'The Alamo' was a big financial gamble for Wayne \/ Everett Collection While the film did net a profit at the box office, it also became a publicity firestorm for Wayne. For one thing, crew members died in a car crash. Then several members caught a particularly contagious case of the flu, not something anyone wants to contemplate for a good while now. As if that wasn\u2019t enough, a woman who worked as an extra, LaJean Ethridge, was murdered by her boyfriend. The Alamo became a cursed film that would help turn some of Wayne\u2019s broke fortune, but at a very steep, dire cost.