'90s Team(s): Minnesota Timberwolves (1993-96), Portland Trail Blazers (1996-99), Atlanta Hawks (1999)
Rider has entrenched himself in the upper echelon of off-the-court athlete screwups. He's been dogged with legal issues extending long after his playing career from assault to drugs. He served roughly four months in prison on cocaine charges. That was in 2007, as of 2011 he was still having run-ins with Johnny Law. His wife thinks the reason is due to a "she-devil, man-hating" probation officer. But his rap sheet makes it hard to give him the benefit of the doubt.
He did an autobiographical documentary called My Testimony: Raw and Uncut. We have absoutely no idea where you can find it. (It doesn't appear to have been released). He's on a semi-path to personal redemption after starting his own charity (Sky Rider Foundation) for underprivileged kids. It's just one of those reclaimations we'll wait to judge.