This program strikes me as a bit absurd, but if it helps some of them, great. I'd prefer they be assigned to read some books about money management - not even investing, just simple personal finance. Maybe The Millionaire Next Door. But then again, I don't work for the NFL.
A great many of these players grew up in families that weren't great at financial management. All of a sudden, they have a lot of money - and they spend it. This isn't uncommon with people (typically poor) who come into a large income, and out it goes.
Also, while the average player makes $1.1M, and only lasts 3.x years, this doesn't mean those players exiting early are making over $3M. There are a ton of players making rookie minimums (the New England Patriots alone just signed over a dozen undrafted free agents); that $1.1M average per year is greatly inflated by the contracts of superstar players: Joe Flacco, Aaron Rodgers, and Tony Romo recently signed huge contracts; Peyton Manning did the same a year or so ago, as did Mark Sanchez. This isn't limited to quarterbacks, either, and there are plenty of players in other positions dragging that average up significantly (Larry Fitzgerald, Vince Wilfork, etc). There are also plenty of players with fairly long careers (not just Brett Favre) dragging up that 3.x year average.
So you have guys who grew up without really learning money management. The NFL tries to educate them on this, but when their parents, siblings, relatives that have come out of the woodwork, friends, and other hangers-on are telling them all these cool things they can spend their money on, what do you expect?
That's not to say the superstars don't have financial problems - plenty have bad investments. If you don't know how to filter investment advice, you're liable to give it to some silver tongued salesman. Heck, there are probably several people on this very board who have received these solicitations - next time you get one, imagine how it sounds if you didn't know what you know about money.
To top it off, they have to be in the league some minimum numbers of years to be fully eligible for lifetime benefits from the league. The ones who just aren't good enough don't get to this benefit level. Hopefully they paid attention in college and got a degree.
That's not to say there aren't players who are good with money. Carson Palmer comes to mind - IIRC, he allows himself $100,000 per year of spending money (debate topic: is that or isn't that mustachian, given his income?). He, like many of us, had a job he didn't like, but because he had sufficient money saved and didn't need the income, was able to effectively quit and go looking for another one. Due to NFL rules, he couldn't just shop himself around, but he was able to force a trade from the Bengals to the Raiders. And now he's with the Cardinals, where I wish him the best of success (his $100,000/year allowance will go much further in Phoenix anyway). Another that comes to mind is Alfred Morris, the Redskins' rookie running back this past season who still drives his mid-90s Mazda 626 that he bought for $500.