No. 2: Reggie Jackson
The Oklahoma City Thunder drafted a young point guard out of Boston College last in the first round of the 2011 NBA Draft. That guard was named Reggie Jackson, and under the Thunder's watch, he developed into one of the better bench players in the league.
When injuries struck Russell Westbrook and the Thunder, Jackson was there ready to step up. He started 36 games in place of Westbrook in 2013-14 and another 13 in 2014-15, and liked the taste of big minutes and big shots he got filling in. He didn't want to go back to being a bench player, but he also wasn't going to be elevated over the multi-time All-Star Westbrook.
Rather than find a way to be a part of what the Thunder were building, Jackson decided he wanted out, to chase that top role somewhere else. Jackson's agent communicated his trade request to the Thunder and made it clear that he would be "resistant to returning to the franchise" should he not get what he wanted.
Sam Presti and the Thunder eventually acquiesced, moving Jackson to the Detroit Pistons in a three-team trade that saw OKC land Utah Jazz center Enes Kanter. Jackson put up a few empty-calorie scoring seasons with Detroit before bouncing around the league; he plays now as the backup point guard on the Denver Nuggets.