Terrell Owens
Terrell Owens played in the NFL for 16 years and played in six Pro Bowl games. Once h retired, he decided to make several investments, all of which turned out not to be in his favor. Despite all of his success, just a few years after retiring he was $400,000 and owed thousands in back child support.
Dermontti Dawson
Dermontti Dawson had a very successful career playing for the Pittsburgh Steelers for twelve years. Throughout that time, he made quite the fortune. However, shortly after he retired, he decided to become a real estate developer. Sadly, this didn’t work out well as in 2010he filed for bankruptcy protection.