Randy Brown
Randy Brown is best known for his time spent playing for the Chicago Bulls from 1995 until 2000. He managed to accrue $15 million during his time in the NBA, but after investing in several restaurants and real estate ventures, he lost a significant amount of money. He managed to turn things around after being hired by the Bulls as director of player development and later assistant general manager.
Randy Brown
Mark Brunell
Mark Brunell had a successful NFL career that earned him about $50 million, which should mean he would be set for life. However, in 2010 he filed for bankruptcy with just $5 million of assets and more than $25 million of debts. He lost a lot of money investing in Whataburger locations that failed and closed down. In 2012, he was hired by the Lions as a quarterback coach so he could get back on his feet financially.
Mark Brunell
