Ken Proxmire, a tool grinder from Michigan, won $1 million in the 1977 Michigan Lottery. Proxmire used his winnings to indulge his inner entrepreneur. He moved to California to open a chain of sporting goods stores.
Several years later, his business went under. $100,000 in debt, Proxmire filed for bankruptcy. His wife left him at that time, too, according to this Time Magazine article. Since his business failure, tax payments and bankruptcy settlements have gobbled up most of his annual winnings.