9. Warren Sapp – Tampa Bay Buccaneers
Unfortunately, this is sort of a sad story regarding the great Warren Sapp who played defensive line for the Tampa Bay Buccaneers. Sapp was one of the most dominant run stoppers in the NFL from 1995 till he retired in 2007. Throughout his career, Sapp also managed to pull down 77 sacks, which was the second most in team history. As successful as he was on the field, off the field, he struggled a bit. With this 15,000 square foot Flordia mansion for example, when he bought it got it for a screaming deal at $7 million. However, financial troubles forced him to file bankruptcy which meant he had to sell his fancy home at auction. Once was all said and done, he had to settle for just $2.9 million, less than half of what he paid for it.