At first glance, a former great player becoming a front office executive or even a coach would seem like a no-brainer. Who better to assemble a championship-caliber roster than a person who experienced sustained success as a player? Who could run a franchise more effectively than a player who once carried it? But when looking at former greats who have transitioned from making plays on the court to executing deals in the front office, the results are varied. 

Given Phil Jackson’s timely departure from the Knicks and Chauncey Billups’s pending deal to head the Cleveland Cavaliers’ front office, one question remains clear: Are the NBA’s GOATs equipped to handle the pressures of executive offices? Here's a look at the good, bad, and downright ugly.