22. Dick Lane
This one is a major step back in time but also proves that crazy spending from NFL stars is nothing new. ‘Night Train’ spent 14 years in the NFL and was a seven-time Pro Bowler. While the Hall of Famer was brilliant on the field, his lifestyle outside was problematic, to say the least. His crazy habits resulted in him losing most of his fortune from the same age-old stories.
Lane developed drug problems and drank like a fish. Then some snake oil salesmen took advantage of him with some bad business deals. Furthermore, three marriages didn’t help matters because those divorce deals aren’t cheap. If you wanted to make a case study of what not to do with your money as an NFL player and compare it to the modern day, you would see very little had changed.