10. Lenny Dykstra

Career Earnings: $36.5M
Net Worth (peak): $58M
Sport: Baseball

Most of us peeped that HBO "Real Sports" profile on Lenny in 2009. We ate that shit up. He was even appearing on Fox Business shows and getting Jim Cramer co-signs. Around that time he was worth $50 million or better, owned a few car wash joints, and was buying stocks like they were going out of style. These days? Oh nothing, just facing grand theft auto charges while on house arrest for bankruptcy fraud. All stemming from Nails buying Gretzky's old mansion for $17 million to flip, and taking on a loan he couldn't afford. So yeah, he made more money after he retired. Apparently lost it, too. Dykstra's net worth today? $-25 million.