2 – Jack Whittaker
In 2002, Jack Whittaker won a Powerball jackpot for $315 million, and after choosing the lump sum payout and paying his taxes, he ended up with $114 million. After he won the lottery, his daughter and one of her friends died from a drug overdose. This led Whittaker to develop a drinking problem, and soon he started frequenting strip clubs. A significant amount of money was stolen from Whittaker’s car, he was hit with several lawsuits, and the rest of his money was stolen out of his bank account due to a scam. Today he regrets ever purchasing that lottery ticket and lives off social security payments.