I'd argue that isn't really that much money. After taxes and paying your agent, it's not like that was life changing money. Especially if you have a mindset you'll keep making that much. If he was super frugal, he could have tucked away a bit, but not the type of money you'd be able to live off of for the long term. Either way, he shouldn't have resorted to swindling! I also wouldn't say it's a certainty that he got at least $100K back in 1999 as a 10th round pick. Even going back to 2006 which is the earliest I can find for 9th and 10th round picks a lot of high school and junior college guys were signing for $60,000-$100,000. There were a few that were going for around $150,000 but this was still 7 years after Hendrickson's draft and most of the guys were making around $100,000 for their signing bonuses.