Cost: $1,500,000 

Deuce McAllister made $70M during his NFL career and managed to blow it all within three years of his retirement. Instead of investing in stocks and bonds, the Saints running back dumps his cash into Versas and Quests by purchasing a Nissan dealership. The lot goes belly up and McAllister's Louisiana home is auctioned off by the Sheriff's office less than a year after hanging up the cleats.