Sports figure(s) involved: Lawrence Taylor
Year: 2010

Most athletes flourish in retirement, but some enter a shame spiral that ends with an appearance on Celebrity Rehab with Dr. Drew. Lawrence Taylor seems destined for the latter. After a handful of arrests during his playing days, Taylor reacquainted himself with the courtroom in 2010 for paying $300 to have sex with a 16-year-old girl. The disgraced linebacker claimed ignorance to the girl's age, dodged jail time, and won his case in civil court, but something tells us this loser's luck is running out.