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"What are you going to do with the money, Michael?"
"Invest in houses, in real estate."
And that's how Michael Larson, the all-time winningest contestant on CBS's Press Your Luck, who appeared on the show in June 1984, lost almost all of his $110,237 in cash and prizes -- investing in a real estate Ponzi scheme. (The rest was stolen from his house -- he had cashed the last $40,000 and left it on the living room coffee table while he and his common-law wife went to a party.) Of course, Larson won the money in the first place by beating the house. He spent six months with a VCR memorizing the patterns of the Whammy board and then spent his last dime traveling to L.A. to get onto the show. After he was broke again, he tried desparately to get back on PYL, but CBS execs -- even though they'd made the board patterns infinitely more difficult since they figured out what happened -- were too scared. Larson died -- where else? -- in Florida, running from the SEC. Bill Murray was slated to play him in the movie version around 2001, but the project never got off the ground.
Side note: Peter Tomarken, who was a seriously underrated game show host, died three years ago when his private plane crashed off the coast of Santa Monica. What was he doing? Only shuttling a medical patient to UCLA for a treatment that the person couldn't afford.