In 1989, Stupak won a widely publicized million-dollar wager on Super Bowl XXIII. Later that year, he won the Deuce to Seven Lowball championship bracelet at the World Series of Poker and the Super Bowl of poker at Caesars Palace, both times edging out world-renowned lowball poker legend Billy Baxter for the championship. One of Stupak's most talked about promotions came when he paid a daredevil one million dollars to jump off the top of Vegas World, then charged him a $990,000 landing fee.