Well, I imagine a "celebrity" retirement is a little different than a regular retirement. These people know their name carries a certain amount of social capital that can be turned into real money. That means a larger estate to leave their kids, bigger trust funds, a yacht, whatever. It must be very tempting, especially considering a lot of these characters are probably being hit up by various groups asking for their paid endorsement all the time. Now that they're in a non-serious part of their career and end of life issues have appeared, its common for them to sign off on things they normally wouldn't have.