The 2000-01 Toronto Raptors and All-NBA wing Vince Carter made it to the second round of the Eastern Conference Playoffs. The franchise would then go 15 seasons before making it past the first round again, missing the playoffs entirely nine times. Chris Bosh came and went without winning a series, and the Raptors endured a lot of losing without a lot of postseason success.
Things changed under head coach Dwane Casey and behind the All-Star backcourt of Kyle Lowry and DeMar DeRozan. In three consecutive seasons they proceeded to win four total series, making the Eastern Conference Finals in 2015-16 and the second round the next two seasons, losing to LeBron James and the Cleveland Cavaliers each time.
DeRozan was a dominant scoring wing in the regular season, but his numbers plummeted in the playoffs and he was an obvious culprit for why the Raptors both were good enough to make the playoffs and win a round, but at the same time drew dead against the conference-leading Cavaliers. If the Raptors were going to break through it would have to be behind a different No. 1 option.
DeMar DeRozan had a ceiling in the playoffs
At the same time, trading DeRozan for a comparable player was merely risking the chemistry of a successful team on a small chance of better postseason success. DeRozan was beloved by his teammates and the Raptors' fan base, a homegrown star who used a dazzling array of moves to get to his spots and pour in the points. If Toronto was going to trade him, it had to be for a clear-cut elite player.
Masai Ujiri, the 2012-13 NBA Executive of the Year, found the player he was going to bet on, and in the summer of 2018 made a blockbuster trade that shipped out DeRozan and took a shot at making a title run. Let's look at the trade and see how it has aged six years later.