Clifford Robinson
Clifford Robinson played in 18 season of the NFL, earning $60 millions throughout his career. However, just two years after he retired, he filed for bankruptcy, though his assets were worth $7.1 million at the time, he owed $12.4 million. He was able to get back on his feet with his Uncle Cliffy cannabis business. He sadly passed away in 2020 when he was just 53 years old.
Clinton Portis
Clinton Portis was once the highest paid running back in the NFL. He eventually signed an 8 year, $50.5 million contract but due to injuries, he was unable to finish his career as he had hoped. 5 years after his NFL career, he filed for bankruptcy after some bad investments. He was later accuse of defrauding the NFL health program, and spent 6 months in jail.