
The Toronto Raptors have been extremely lucky to have one of the best executives in league history in Masai Ujiri steering their ship over the last few years. Ujiri took a team that had never made it to a Conference Finals and had them winning a title in a dominant fashion within a decade.
Ujiri helped the squad by drafting stars like OG Anunoby and Pascal Siakam very late in the draft, but his best and most consistent way of improving the roster has been making trades. Ujiri is not one to be tricked when it comes to this area of roster building.
Ujiri’s mix of patience with regard to negotiation and aggression when the right player becomes available has helped him have one of the best ratios of trade wins to trade losses in the league. The Raptors may not be trading with half the league every month like some more active GMs, but Ujiri’s few big trades have shaken the NBA.
These four trades stand out as the best moves Ujiri has made in his career with the Toronto Raptors. While the team trading with Ujiri has often been left in a worse spot, Masai built the foundation of some consistent winners on the back of these heists.
Toronto Raptors: 4 best trades Masai Ujiri has made.
4. Norman Powell for Gary Trent Jr.
Powell and Trent have similar styles of play, but the proven veteran in line for a payday looked like a better fit for Portland at the time. Trent, still coming into his own, looked more likely to fit Toronto’s new-look timeline. Just a year later, this trade seems horrendous for Portland.
Powell was effective for Portland and parlayed his performance into a five-year contract, but he only lasted one season with the Trail Blazers. Powell was traded to the Clippers for a largely underwhelming package, while Trent managed to improve upon his flaws with Toronto and earn himself a deserved $51 million contract.
Toronto Raptors: Masai Ujiri won the Norman Powell trade.
While the Raptors were able to get a promising young player in Trent thanks to his poor defensive play in Portland, Toronto turned him into a turnover machine while helping him put together the best offensive season of his career. Trent could easily be in for a nine-figure payday.
Two of the three parties involved in those two connected trades have come out of these proceedings smelling like a rose. Powell will chase a championship with the Clippers, and the Raptors found a perfect replacement in Trent. The Blazers have been left with a box of scraps.

3. Serge Ibaka for Terrence Ross
The Raptors may have ended up making it to the NBA Finals without Ibaka in the fold, but his ability to block shots and drain 3-pointers helped Toronto pull out some very close victories in that run. Considering what they fit him for, the Ibaka trade was an absolute steal for Toronto.
Terrence Ross was the piece sent to Orlando in the Ibaka deal. While he is performing better with the Magic than he ever did during his Toronto tenure. The trade hasn’t moved the needle for Orlando, but it made a world of difference for the Raptors in 2019.
Toronto Raptors: Serge Ibaka is better than Terrence Ross.
Ross has averaged 13.3 points per game in his five and a half seasons with the Magic, which is much better than the 9.5 he managed to scrape together with the Raptors. Ibaka, meanwhile, averaged 14.2 points and 7.4 boards per game on some of the best teams in the East.
The Congolese big man quickly became one of the most beloved Raptors that ever put those red and black jerseys, as the gregariousness he brought to the locker room and skill he flexed on the court was much more impactful than a garden variety bench bucket-getter like Ross.

2. Greivis Vasquez for OG Anunoby and Norman Powell
Vasquez was a reputable point guard in his day, but he was nothing too special during his time with the Raptors. Milwaukee thought that Vasquez was the missing ingredient to their backcourt in 2015, but the trade ended up giving Toronto the wing depth they needed to become a champion.
Powell, who was picked No. 46 overall in 2015, was sent to Toronto with the pick that eventually became OG Anunoby. With Powell’s smooth shooting and Anunoby’s rugged two-way play, the Raptors were able to finally surmount a mountain many thought was unreachable for this franchise.
Toronto Raptors: The Greivis Vasquez deal was a steal.
Anunoby has not only become a terrific defender, but his offense has improved every year he’s been in the league. Even though he was picked 23rd overall, Anunoby’s offense has evolved to the point where only injuries and a lack of tremendous volume have blunted his All-Star potential.
Vasquez would average 5.7 points and 4.0 rebounds per game in just 23 games with the Bucks. After three meaningless games on a laughable post-Jayson Tatum trade Nets team, his NBA career was done. In terms of the raw value Ujiri got for Vasquez, this might be the clearest win he’s ever had in a trade.

1. Kawhi Leonard for DeMar DeRozan
Very rarely can a franchise be said to have convincingly won a trade in which they surrendered arguably the best player in franchise history and acquired someone who would bolt in free agency the following year. However, the Leonard trade remains the most pivotal moment in recent Raptors history.
Leonard only had one year had with the Raptors, but what a year it was. Averaging 26.6 points per game with tremendous efficiency was one thing, but essentially carrying the team on his back during a dominant postseason run made this the best one-and-done season in NBA history.
Toronto Raptors: Masai Ujiri is a champion because of Kawhi Leonard.
While DeRozan had some quality seasons with the Spurs, and Jakob Poeltl has since evolved into one of the best rim protectors in the sport, no Raptors fan would press the reset button and negate this trade if given a chance. Kawhi will always be Raptors royalty as a result of this season.
How many executives would have held onto DeRozan due to his connection with the franchise and concern over Leonard’s future? That willingness to throw all of those factors into the trash and send this trade through shows Ujiri’s savvy evaluation skills.

