No. 6: Glen Grunwald
Glen Grunwald was a high school All-American and the captain of an Indiana University team that won the National Championship. That Hoosiers team was led by a dynamic point guard named Isiah Thomas, and years later when Thomas took the job running the Toronto Raptors, he brought Grunwald with him as his No. 2.
When Thomas' power play failed in 1997 and he left the team, Grunwald was left to try and hold things together, and he failed miserably. Rather than find a way to reconcile with star Damon Stoudemire, who was upset at Thomas' departure, Grunwald traded him at midseason. That caused head coach Darrell Walker to quit in protest, and a Raptors team without its leader and coach spiraled to a 16-66 record at the bottom of the standings.
Grunwald completed the trifecta that summer, trading promising big man Marcus Camby, who would go on to be a difference-making defender elsewhere. In just six months the Raptors completely reset, halting their momentum as a franchise and effectively going back to square one. Much of that blame is on Thomas' shoulders, but Grunwald bears a lot as well.
To Grunwald's credit, he then took the pieces of that team and built up the Raptors' first playoff team, adding Vince Carter as the centerpiece and building around him. Toronto even won a playoff series in 2001.
Then he did it again. The Raptors were plagued with injuries in 2002-03 and missed the playoffs, and Grunwald began another frenetic teardown. He replaced the head coach, traded away starting center Antonio Davis and took a good team and sent them spiraling back into the lottery, a chaotic destruction that led to Vince Carter demanding a trade out, and Grunwald being fired before the 2003-04 season even ended.
Grunwald's inability to handle a team in adversity and his propensity to pull the ripcord instead of sitting in the tension of adversity and leading his team out of it, are why he appears on this list of people who turned their back on the Raptors.