Mark Brunell
With the 118th pick in the 1993 NFL draft, the Green Bay Packers selected Brunell from the University of Washington. The only problem for Brunell was the Packers already had some guy named Brett Favre, so playing time was scarce. Over the next two years, Brunell appeared in just two games with the Packers and was eventually traded to the Jaguars for a 3rd-round and 5th-round pick. During his time in Jacksonville, Brunell developed into one of the most versatile quarterbacks in the league, resulting in three trips to the Pro Bowl.
Brunell was active in investing his NFL earnings into other business ventures. In 2011, news broke that Brunell had lost almost all of his career earnings ($50 million) due to failed businesses, forcing him to file for bankruptcy. According to court documents, Brunell sank his earnings into nine businesses, five of which failed. A majority of his fortune was spent (and lost) on real estate projects and fast food chains, both in the Jacksonville area. Brunell spent some time as an analyst with ESPN before becoming quarterbacks coach of the Detroit Lions in 2021.