These things can happen, but the guy got like a $10 million bonus at one point from Detroit, plus salary for 14 years. That's set for life money. Take a couple million of that and put it somewhere you never touch it and let it grow slowly but 99% safely. Insure yourself out the ass to protect yourself from liabilities like this. Then if you want to take some risks, fine.
I realize that most guys are chewed up and spit out and have no NFL cash left in 10 years, but seriously... Sounds like Charlie invested badly. A lot of guys invest in real estate, car dealerships, restaurants, and think it's a quick way to parlay money into bigger money.
My BiL was obsessed with getting on So You Want to Be a Millionaire back when it first hit. They had different rules for getting on the show in the beginning, basically you call in and randomly selected people moved on to over-the-phone trivia quizzes that culled out potential entrants. He entered everyone he could think of. His wife, Mrs. F's sister, got selected, and off to NYC she went. I was one of 5 phone a friends because of her misperception of my intelligence. Long story short, she makes it to the hot seat, I got a call and correctly answered the $16K question off of some whiff of memory of the Donner Party (no Internet lookup at the time), and she wins $64K. 11 years ago, that ain't bad coin for a day's work. Ain't bad for a day's work now. The Mrs. and I got a small gift, very small piece of the pie, but it went to our house down payment, which was cool. The BiL, now former BiL, was an astute dude, very sharp. Decided to invest heavily in tech stocks, which kept going up faster than the savings rates at banks, and of course from that short-term bump he could pay off the tax hit. Except this was when the tech bubble burst. And he didn't partition the money into stocks and CDs or bonds or even plain old bank savings. It was all in tech, and once the tax bill hit they were in hock for a few years.
The want of money, and all that. Even the smartest among us can't resist the quick hit for monetary gain. How many lottery winners manage their money intelligently?
Charlie can work back his private wealth by coaching QBs for us the next decade or so.