Masai Ujiri Is Living On Borrowed Time; Leading The Toronto Raptors’ Front Office

Masai Ujiri has been with the Toronto Raptors organization since 2013 when he replaced Bryan Colangelo as vice president and general manager.

The legacy of what Masai Ujiri has done for the Toronto Raptors organization and its fans will live on forever. Ujiri took over a team that lacked an identity in 2013 and turned them into eventual NBA champions.

He traded big man Andrea Bargnani to the New York Knicks, securing a first-round pick. That move unofficially handed over the reins of the team to Kyle Lowry and DeMar DeRozan.

Lowry and DeRozan then, somewhat unexpectedly, proceeded to lead this team to the playoffs repeatedly.

When they couldn’t get over the hump, failing to ever truly establish themselves as a threat in the Eastern Conference while LeBron James was there, Ujiri was not content with mediocrity.

He traded beloved Raptors star DeMar DeRozan (and other assets) for a true superstar, Kawhi Leonard. With the later addition of Marc Gasol, the team won the 2019 NBA title over the shorthanded Golden State Warriors.

Ujiri earned himself a lot of good will from the organization and fans alike for what he had accomplished. A plethora of good trades, good draft picks (like Pascal Siakam, OG Anunoby, etc.) and a relentless desire to win made Ujiri very popular.

However, when looking at the more recent missteps of the front office, the magic has faded and so has the good will.

While Ujiri should also receive credit for drafting current frontman Scottie Barnes in 2021, there have been plenty of questionable decisions after the 2019 championship.

After Kawhi Leonard left, there was a massive superstar-sized hole to fill on the Raptors. The team was still competitive the following season, but they lacked the x-factor Leonard brought in their quest for a repeat.

Ujiri gambled on Siakam being able to step into that role with time, but those shoes were too large for him to fill at any point in the Post-Leonard era.

The front office was hellbent on building around the core of Siakam-VanVleet-Anunoby. They got a lift of optimism when Barnes joined the fold, but their peak was a first round exit during the 2022 playoffs.

Ujiri building around this core resulted in some baffling lowlights.

During that 2022 season, he offloaded guard Goran Dragic to the San Antonio Spurs for veteran Thaddeus Young. They gave up a first-round pick in the deal that should have been used to build towards the future instead of maximizing that group.

The following season, he doubled-down on winning with this group and traded another first round pick amidst an underwhelming year to bring back center Jakob Poeltl to Toronto.

In a vacuum, Poeltl is a good player and Toronto needed help at the center position. However, they barely got back to .500 with a record of 41-41 before getting eliminated by the Chicago Bulls in the Play-In Tournament.

Ujiri went all in on a core that was not yielding results worthy of that faith. Furthermore, it was a core that had upcoming contract decisions.

Thankfully for him, key contributor Gary Trent Jr. decided to pick up his player option. Jakob Poeltl was also retained. However, former All-Star Fred VanVleet left for nothing and joined the Houston Rockets.

Instead of deciding to blow it up and build around the promising Scottie Barnes, Ujiri kicked the can down the road. He brought in guard Dennis Schroder to fill the void.

All this while staring down the questions of what to do with the contracts of Siakam and Anunoby that would expire in the 2024 offseason.

When an opportunity presented itself to bring in a superstar again, Damian Lillard, Ujiri whiffed on it. The Raptors were reportedly unwilling to part with Anunoby. He would get traded the following season when the Raptors were, predictably, a bad team.

The damage had been done to Siakam’s value as well. As an expiring contract, trading the two-time All-NBA forward yielded a modest return at best. Schroder was then moved for cap space half a season into his first year with the Raptors.

While Ujiri has done tremendous work in the past turning around the fortunes of the Raptors, it is fair to wonder how much longer he will have his position if he does not adequately build a contender around Barnes moving forward.