Isiah Thomas - Beyond His Abilities
Isiah Thomas was a phenomenal basketball player with an engaging personality. But his post-NBA career has been an example of living above your competency. He hasn't shown success in anything he's done--a couple GM positions, a couple coaching position. He killed an entire basketball league when he helped buy it (the Continental league, which had a team here in Fort Wayne). And now his stupidity has cost his employer $12 million. And he's still young, with many years in which to wreak further havoc.
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You are right. Thomas has had what could be described as a reverse midas touch. He had allegations of personal and business misconduct with the Raptors when he was part owner. He left Toronto and bought and bankrupted the CBA. Then as coach he helped bring the Pacers back down to mediocrity after Larry Bird got them to the Conference Finals the previous year. He finally settled in with the Knicks front office where one of the leagues highest payrolls has produced absolutely nothing, all capped off by the recent court case.