37. Denny McLain
Criminal History: Drug trafficking, embezzlement, money laundering, mail fraud
Time Behind Bars: Eight years
Student loans are a pain in the ass but if you want a truly crippling debt, get in deep with the Syrian mob. With his career tanking and out of money by the mid '70s, Denny McLain made the awkward transition from major league pitcher to loan shark and was ultimately indicted by the Federal Government.
In addition to having his toes dislocated with a heel stomp by one of his "coworkers," McLain was convicted of extortion and cocaine trafficking. After a three year prison stint and with his life seemingly back together, the Tiger pitcher was convicted on charges of embezzlement, money laundering, mail fraud and conspiracy, after taking almost $3M from a company pension fund in the mid '90s.