3. Masai Ujiri (President, Toronto Raptors)
- Organizational record: 355-219 (61.8%) (2013-2019)
- Best Move: Trading DeMar DeRozan, Jakob Poeltl, and a protected 2019 first-round draft pick to the San Antonio Spurs for Kawhi Leonard and Danny Green. (2018)
- Worst Move: Selecting Bruno Caboclo with the 20th overall pick in the 2014 NBA Draft. (2014)
We’ve said it before, and we’ll say it again: Masai Ujiri is the greatest front office employee the Toronto Raptors have ever had, without question. A large part of his success is making moves other executives would be afraid to make.
He fired a Coach of the Year in Dwane Casey, replacing him with a rookie head coaching hire in Nick Nurse. He traded away a franchise icon from a 60-win team for a player who hadn’t played real basketball in over a calendar year. During the middle of this season, there were rumors he tried to trade away Kyle Lowry. If there is one thing Masai has shown over the years, it’s that he’s unafraid to make the tough decision.
But Masai is not only a bold decision-maker. His moves around the margins are what have allowed him to be so successful.
Granted, his selection of Bruno Caboclo (forever two years away from being two years away) at 20th overall in 2014 does leave a singular red mark on his otherwise-unimpeachable record, but his drafting has largely been spectacular. He’s hit on later picks such as Delon Wright (20th overall in 2015), Jakob Poeltl (9th overall in 2016), OG Anunoby (23rd overall in 2017) and, of course, Pascal Siakam (27th overall in 2016).
His trades have also been a source of awe and wonder for Raptor’s faithful. His acquisition of Marc Gasol for pennies on the dollar brought Toronto their first championship. Before that, he turned Jared Sullinger and two second-round picks into P.J. Tucker. Before that, he got Norman Powell and a first-round pick from Milwaukee for Greivis Vasquez. For Pete’s sakes, the man turned John Salmons into Lou Williams!
Ujiri mentored a young franchise through the trials and tribulations of multiple playoff exits at the hands of one of the greatest players to ever live. Ujiri pushed all the right buttons, even when they bordered on the emotionally unbearable. And now, as the Toronto Raptors face an uncertain future, they know one thing for sure: there’s almost no one else they’d rather face it with.