Dick Lane
After Dick Lane spent four years in the Army, he walked into the Los Angeles Rams offices in 1952 and asked whether he could have a job playing football. After making the team, Dick “Night Train” Lane went on to play as a defensive back and became one of the most prolific during the ‘50s and ‘60s, ultimately becoming an inductee on the Hall of Fame. After his long football career, he experienced some difficult times which involved drinking, illicit drugs, and bad business deals. This is the reason why he lost a large part of his fortune.
Bernie Kosar
Bernie Kosar is a former Cleveland Browns quarterback who played for the team from 1985 to 1993 and had two short stints with the Dolphins and the Cowboys before retiring in 1996. After he retired, he went into various business ventures which never really panned out. He filed for bankruptcy in 2009 and had an $18.9 million debt, so the government seized some of his properties and some were foreclosed. He owed over $173,000 in taxes to the state of Ohio.