The problem with a lot of these athletes is that they're vastly ill-equipped to handle their own finances, and so they surround themselves with 'experts' to do the heavy lifting for them.
But those parasitic 'experts' are only, and obviously (at least in retrospect), interested in enriching themselves, and have no loyalty or allegiance to their big meal ticket.
The parasitic hosts slowly but surely drain the host's blood dry, by not just being yes men and women, as they cater to and encourage every desire for instant gratification their host has (as they sneak more cash into their pockets), but by often engaging in fraud and deception, also. It's part negligence and part overt maliciousness.
Sadly, this entourage of trusted inner circle members sometimes encompasses even family members, who actually steal from their own flesh and blood, without reservation.
There are exception to this happenstance, however.
I doubt that you'll ever see Sugar Ray Leonard, Tiger Woods, Lenny Dykstra, Larry Bird, Pete Sampras, Andre Agassi, Brett Favre, Isiah Thomas or countless other athletes in this situation.
They watch their assets and the people that watch their assets closely, and demand competence of themselves and those they employ.