Dan Marino
Prominent Miami Dolphins quarterback Dan Marino broke a lot of records, earned several awards, and made a lot of money during his NFL career. After his retirement from pro football, he worked as an analyst and a sportscaster, but a bad business move caused him to almost go broke. In 2012, Tupac Shakur was resurrected as a hologram at the music festival Coachella. Impressed by this, Marino bought more than 1.5 million shares of Digital Domain, the company which produced the technology. However, that business eventually went bankrupt, which caused Marino to lose roughly $14 million.
Chris McAlister
Former NFL cornerback Chris McAlister played for eleven seasons, mainly with the Baltimore Ravens. Since he was a great player, by the time his football career ended, he had earned around $45 million. In spite of his massive earnings, McAlister managed to blow most of it after his retirement from the NFL and even had difficulties paying child support (which was reportedly only $3,000).