Draft Selection: 3rd Overall, 1992
Length Of NBA Tenure: 1992-2005
Accolades: 1997 NBA All-Star

After leaving the game of basketball in 2005, Christian Laettner joined former Duke teammate Brian Davis to take on a variety of failed ventures. After the court required Laettner and Davis to repay the loans they received from Scottie Pippen ($2.5 million) and Shawne Merriman ($3.8 million), they went on to assume operating rights to the MLS' DC United but sold their stake in 2009 to create a business that would convert warehouses into condos and real estate spaces.

Over time, their venture amassed a debt upwards of $30 million. So far, they've avoided any jail time for failing to repay those debts, however, that may not be the case for long. Oh, and did we forget to mention how these two attempted to buy the Grizzlies in 2006 but their $252 million bid fell through? Yeah, we wonder why.