Mark Brunell

Mark Brunell had a very successful NFL career. His best years were spent in Jacksonville, where he set 36 Jaguars franchise records. But his career didn’t end there. He spent 17 seasons in the league, playing for 5 teams. He even picked up a Super Bowl ring with the Saints in 2010.

You spend that long in the NFL as a quarterback, you manage to earn quite a bit of money. Over $50 million to be exact. Several failed investments that did not pan out cost Brunell quite a bit of money. He’s recouped that these days and now spends his days working as a high school football coach in Jacksonville.