Some of the older crowd may remember Linda Evans, one of the stars of the 80's TV drama Dynasty The LKF is that Evans shot the famous film of Evel Knievel cracking up when he tried to jump the fountains at Caesar's Palace. (link below, starts at :21) Knievel had hired movie director John Derek to film the attempt, and to save money, Derek put Evans, his wife at the time, on one of the cameras.
The poster child for sports futility has got to be NASCAR driver J.D. McDuffie. In 653 starts in the top series (Monster Cup, Winston Cup, etc.) not only did he never win, he never even finished a race on the lead lap. If you're wondering how someone kept giving this guy a ride, he owned his own cars.
Sounds like some rich guy who just wanted to say he was a driver. I've heard that the best way to make a small fortune in NASCAR is to start with a large fortune.
As Auric Goldfinger said to James Bond (in the book, not the movie), "The safest way to double your money is to fold it in half and put it back in your pocket."