Travis Henry
Travis Henry played seven season in the NFL, playing for the Buffalo Bills, Tennessee Titans, and the Denver Broncos. Once he retired, things got out of hand for Henry. Since he had nine children with nine different women, he had a lot of child support to keep up with, which he failed to do. His annual child support payments came out to $170,000!
Lenny Dykstra
Lenny Dykstra is known for playing baseball for the New York Mets between 1985 and 1989. Despite this, he ended up losing all of his money and even landed himself in jail for a grand theft auto charge. He filed for bankruptcy in 2009 after being $31 million in debt and having to sell most of his possessions.