From Andrea Bargnani to Kawhi Leonard, ranking Masai Ujiri’s top five trades with Raptors

In the hours leading up to the 2023 NBA trade deadline, the Raptors remain the team that everyone is watching.

After Wednesday night’s win over San Antonio, Toronto finds itself at No. 10 in the Eastern Conference standings with a 26-30 record. The Raptors may believe that this season is unsalvageable and decide to send out some of their top players for future assets, or they could go into buyer mode and attempt to make a playoff push.

Regardless of what happens next with the Raptors, they will once again rely on one figure to guide them through the deadline: team president Masai Ujiri.

And that faith in Ujiri is well earned. Throughout his tenure in Toronto, he has been able to pull off some franchise-changing deals.

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5. Andrea Bargnani to Knicks for Marcus Camby, Steve Novak, Quentin Richardson, 2014 second-round pick (became Xavier Thames), 2016 first-round pick (became Jakob Poeltl) and 2017 second-round pick (became Jonah Bolden)

This was an incredibly confusing trade from the Knicks’ perspective when it happened — and it only looks worse in retrospect. Bargnani was coming off a season in which he averaged 12.7 points per game and shot below 40 percent from the field.

The Raptors should have been required to attach picks to Bargnani in order to move him, but they somehow got multiple picks back for him in addition to the Knicks players. This was an absolute heist by Ujiri.

4. Terrence Ross and 2017 first-round pick (became Anzejs Pasecniks) to Magic for Serge Ibaka

Ibaka may not have been the same defensive force with the Raptors that he was during his Thunder years, but he was still a strong frontcourt addition. He averaged 14.2 points, 7.4 rebounds and 1.2 blocks per game in Toronto, and he was a key member of the 2018-19 championship squad.

Ross turned into a solid bench scorer for the Magic, but Pasecniks didn’t last long in the NBA. Ujiri managed to elevate the frontcourt without losing much in this trade.

3. C.J. Miles, Jonas Valanciunas, Delon Wright and 2024 second-round pick to Grizzlies for Marc Gasol

Ujiri’s 2019 trade deadline gamble paid off in a big way. Gasol was the missing piece that pushed the Raptors over the top.

While he didn’t post stunning counting stats, Gasol was undoubtedly an upgrade over Valanciunas on the defensive end and as an offensive connector. He was the exact kind of interior presence that Toronto needed in a tough series against Joel Embiid and the 76ers.

2. Greivis Vasquez to Bucks for Norman Powell and 2017 first-round pick (became O.G. Anunoby)

Just stare at that trade for a second. Vasquez for Powell and Anunoby? It was lopsided enough with just one of those guys.

Powell enjoyed five-plus seasons in Toronto, averaging 16.0 points on 49.5 shooting from the field and 39.9 percent from 3-point range after the title season. Anunoby has emerged as one of the best defenders in the league, and Ujiri may end up flipping him at the 2023 deadline for a huge package.

1. DeMar DeRozan, Jakob Poeltl and 2019 first-round pick (became Keldon Johnson) to Spurs for Danny Green, Kawhi Leonard and cash

Everyone knew where this list was going. Ujiri traded away a fan favorite in DeRozan, but he acquired an eventual Finals MVP in Leonard and a starting shooting guard in Green.

Considering the cost of All-Stars in recent transactions, this deal has only aged like a fine wine. This is the defining moment of Ujiri’s front office career.