28. Rick Pitino
Pitino is famously (or infamously) known for his time on the collegiate level. Transgressions aside, the man knows how to coach on that level. When it came to the NBA, this wasn’t the case. Pitino floundered brilliantly as the Celtics head coach. In four years, he accrued a 102-146 record. Pitino hated being in Boston so much, that he resigned from the post despite being owed more than $20 million — and having six more years on his deal.
Image Source: Andy Lyons/Getty Images