Vince Carter
It’s crucial to not keep an athlete who doesn’t want to play for a franchise. This is a nightmare that no head coach wants to deal with because it creates a negative atmosphere in the locker room. The Raptors discovered this after Carter lost patience with the organization. He became an icon in Toronto but demanded a move South.
However, the Raptors resisted and tried to persuade him that they were going in a positive direction. Carter’s performances declined and this dragged on for months. Finally, Toronto realized that they didn’t have a choice and sent him to New Jersey in a lopsided trade. Toronto booed their former hero every time he came North again (via Fansided).