A lot of people mock athletes for blowing signing bonuses and contract extensions, but a half dozen concussions and three semesters at Florida State don't exactly prime the pipes for a sophisticated investment portfolio. If your most productive income years were your 20s, you'd probably have a few foreclosures under your belt, too. Sure, with some responsible asset management most of these guys would be fine, but when you have the immediate gratification of cheering crowds and groupies, serial maturing bonds don't seem so exciting.