4. DeMar DeRozan
DeRozan, Jakob Poeltl, and one first-round draft pick were the return for Kawhi Leonard and Danny Green in 2018. The Claw’s injury and reasons for wanting to leave the Spurs are well-documented, but he led the Raptors to a championship in his lone season in Toronto. San Antonio’s return was depressed by his rental status, but DeRozan was a four-time All-Star that led his team to the conference finals in 2016.
He instantly developed a one-two punch with LaMarcus Aldridge as the Spurs won 48 games in 2019. They were knocked out in the first round of the playoffs, and things only went downhill from there. DeRozan continued to score over 21 points per game as he took his playmaking to another level, but the Spurs won just 65 games combined over the next two seasons.
It was the first time they missed the playoffs since 1997, and it was clear they were not going anywhere. The San Antonio Spurs traded DeMar DeRozan to the Bulls in 2021 for Al-Farouq Aminu, Thaddeus Young, one first-round draft pick, and one second-rounder. It was a fine return, but they paid a higher price and DeRozan made two All-Star appearances in Chicago.
They failed to realize the 6’6 wing was not the answer and could have traded him for more if they had not waited until they were in a full rebuild.