The Dallas Mavericks shocked the basketball world on Monday morning by hiring veteran executive Masai Ujiri as their new President of Basketball Operations and Alternate Governor. Ujiri enjoyed largely successful stints as the top decision maker with the Denver Nuggets and Toronto Raptors throughout the 2010s, winning both an Executive of the Year award and an NBA title during that time. He was let go by the Raptors in June of 2025.
Though Ujiri’s track record through 2019 is virtually bulletproof, the last few years of his Toronto tenure were tumultuous to say the least. After winning the 2019 title, the Raptors became imprisoned in mediocrity from 2020 to 2023 before finally embarking on a long-overdue rebuild. According to reporting around the organization, this was in large part due to a mandate from ownership group Maple Leaf Sports & Entertainment. Chairman Ed Rogers had no interest in a rebuild so soon after winning the title, and Ujiri was prevented from hitting the reset button at an ideal time.
But even factoring in the troublesome Toronto ownership piece, Ujiri’s final six years in Toronto can’t be described as anything less than a failure. Is this guy cooked? Has the game passed him by? OR was Ujiri fed up with Toronto ownership, mentally checked out during the final years of his tenure, and desperate for a break and change of scenery? With these questions in mind, let’s take a hard look at all the major moves Ujiri made after winning the 2019 title. Through the good, the bad, and the neutral, we might be able to discern whether Ujiri can rediscover his fastball and build a winner around Cooper Flagg.
June 2021- Toronto selects Scottie Barnes fourth overall in the NBA Draft
This is by far the best move of Ujiri’s post-title tenure. Barnes has blossomed into a superstar for the Raptors, a top-15 player worth building a franchise around. And while it may seem like giving Ujiri credit for hitting on the fourth overall pick is a bit generous, Barnes wasn’t the consensus best player available when Toronto made their selection. After Cade Cunningham, Jalen Green, and Evan Mobley were off the board, many assumed the Raptors would take Jalen Suggs with their pick. Others argued for guys like Jonathan Kuminga or Franz Wagner. At the time of the draft, The Ringer, The Athletic, and SB Nation had Barnes ranked fifth, sixth, and seventh, respectively, on their big boards. This wasn’t a no-brainer pick at fourth overall, and Ujiri nailed it.
August 2021- Toronto signs & trades Kyle Lowry to Miami for Precious Achiuwa and Goran Dragic
You could argue that Toronto should have traded Lowry a year earlier, but Ujiri did well to avoid paying him a three-year mega contract while getting something in a sign-and-trade. Lowry was a franchise legend and had played an instrumental part in delivering their first title, so he had a lot of say in whether he stayed or went. When it became clear that his time as a Raptor was over, Ujiri worked with his preferred destination to facilitate a deal. And though Dragic infamously did not work out, Achiuwa did enough to establish himself as a rotation player in the league. Ujiri dodged a bullet by not paying Lowry, who declined dramatically in Miami. This should have launched the rebuild in earnest, but OG Anunoby and Pascal Siakam were too young to trade and too good to bottom out.
June 2024- Toronto acquires Davion Mitchell, Jamal Shead, Sasha Vezenkov, and a 2025 2nd round draft pick from Sacramento for Jalen McDaniels
If you want to fleece someone, call the Sacramento Kings. This return was highway robbery for Jalen McDaniels, a player not to be confused with his much more talented brother. Sacramento made this trade to duck the luxury tax, and Ujiri smartly preyed on their desperation, snagging a good role player in Mitchell and a rookie flyer in Shead. The latter’s defensive prowess should allow him to maintain a rotation role in Toronto for a long time. This was a nice bit of business from Ujiri that went under the radar when it happened.
February 2025- Toronto acquires Brandon Ingram from New Orleans for Bruce Brown, Kelly Olynyk, a 2026 1st round draft pick (from Indiana), and a 2031 2nd round draft pick
The last major deal of Ujiri’s Raptors stint was a blockbuster. And though it may be a controversial take, I think this was a good deal from a process and value standpoint. Ingram’s value was depressed at the time, and Ujiri saw an opportunity.
As I’ll detail later, the Raptors have had a tough time attracting free agents, and Ingram represented a chance for them to add an All-Star on the relatively cheap. They essentially gave up one first-round pick and some garbage. And look, here’s where it gets thorny— that pick is currently slotted as second in the 2026 NBA Draft. Now, it looks like Toronto paid a hefty price for Ingram. But a year ago, who could have foreseen Tyrese Haliburton tearing his Achilles in the NBA Finals, triggering a supertank gap year from Indiana, and exponentially inflating the value of their draft pick? I suppose that’s the danger in dealing those assets, but I think this was solid process by Ujiri. Ingram was fantastic for Toronto this season, making the All-Star team and helping them to the fifth seed before injuries ended his season.
November 2020- Toronto drafts Malachi Flynn 29th overall over Desmond Bane
Ujiri has mostly nailed the draft throughout his career, and lots of people passed on Bane, but this one hurts. Flynn was a bad basketball player, and he wasn’t even the usual archetype Ujiri goes for. You would have hoped that he would have recognized Bane’s obvious talent instead. Making the wrong pick one slot before Bane went adds insult to injury.
March 2021- Toronto trades Norman Powell to Portland for Rodney Hood and Gary Trent Jr.
This was the first big blunder of Ujiri’s 2020s run. I understand the process here— Ujiri decided he didn’t want to pay Norman Powell entering his age-28 season and flipped him for a guy (Trent Jr.) of a similar archetype who’s nearly six years younger. Trent had a couple of good years in Toronto, but it’s clear that Toronto gave up on Powell too quickly. Paying him the modest $18 million AAV contract he got from the Clippers would have been a solid investment.
February 2022- Toronto trades Goran Dragic and a 2022 1st round draft pick to San Antonio for Thaddeus Young, Drew Eubanks, and a 2022 2nd round draft pick
While this trade wasn’t that consequential, it was bad process. Toronto was on a hot streak heading into the deadline and looking to bulk up for the playoffs, and Ujiri thought that Thaddeus Young was the guy to put them over the top. They dangled Dragic’s expiring contract and the 20th overall pick (essentially moving down 13 spots) to acquire the veteran forward. Young gave Toronto very little during his tenure, and Ujiri was wrong in believing he had more left in the tank. The pick they gave to San Antonio ended up being Malachi Branham, who stinks. But they missed the opportunity to draft Walker Kessler, Andrew Nembhard, Christian Braun, or Peyton Watson, all of whom would have been great additions for the future.
February 2023- Toronto acquires Jakob Poeltl from San Antonio for Khem Birch, a 2023 2nd round draft pick, a 2024 1st round draft pick, and a 2025 2nd round draft pick
Again, value-wise, this isn’t a bad deal. Poeltl was still a very good player at the time, and Toronto only gave up one significant pick for him. And the 2024 draft was horrible, so the eighth-overall pick they gave up (Rob Dillingham) doesn’t hurt that much. Ultimately, this trade was a failure because of what it represented in a timeline sense. Toronto was clearly staring a rebuild in the face, and trading a lottery pick for Poeltl, a good, not great center, didn’t make any sense. He didn’t make the team any better, and they had to rebuild the next year anyway.
July 2023- Toronto loses Fred VanVleet for nothing in free agency
VanVleet has opened up about his desire to leave Toronto before the 2023 offseason. The Raptors weren’t good that year, but they didn’t trade VanVleet at the deadline because Ujiri wanted to push for the playoffs. Maybe the offers weren’t great, but they likely could have gotten something. Instead, they finished .500, lost in the Play-In, and let a franchise legend walk for nothing.
December 2024- Toronto trades OG Anunoby, Precious Achiuwa, and Malachi Flynn to New York for R.J. Barrett, Immanuel Quickley, and a 2024 2nd round draft pick
There’s no way around it; this was a disastrous trade for Ujiri. He dealt Anunoby when his value was at its lowest in years and failed to get back a single first-round pick. Sure, Barrett has turned into a nice player for them, but the contract Ujiri gave Quickley after the deal basically negates that. After seeing the leap Anunoby took in New York, it’s painful to see just how little Toronto got back for his services.
July 2024- Toronto signs Immanuel Quickley to a 5-year, $162.5 million contract
This was just a crazy overpay by Ujiri. Quickley isn’t a bad player, but he’s a one-way guy who doesn’t guard at 6’2. Giving him $32.5 million per year never made sense because that’s a number you give someone if you anticipate a star leap on the way. Nothing about Quickley’s game made it seem like that was possible. A contract like this on the books for a non-star player (with injury issues) makes team building really difficult.
February 2025- Toronto trades Davion Mitchell to Miami in a five-team deal that nets them PJ Tucker and a second-round pick (Jimmy Butler trade)
2025 PJ Tucker was unquestionably cooked like the Christmas goose. Why did Ujiri feel like he had to force his way into the Jimmy Butler trade so he could give up a good role player for this guy? It was apparently just salary dumping Mitchell and getting a second-rounder in the process. After Ujiri was fired, they flipped that pick to the Warriors for Trayce Jackson-Davis, who stinks. I bet they wish they had Mitchell back, because they didn’t use that cap relief for anything.
Most of the transactions Ujiri made in the 2020s fall into this category. Here are some highlights:
Trading a first-rounder for Kelly Olynyk and Ochai Agbaji: This is one of the more “sure, why the hell not” deals in league history. Ujiri traded the 29th pick in a bad draft (Isaiah Collier) for two okay role players who played decently in Toronto, and Olynyk helped them get Ingram later. Perfectly adequate.
The Pascal Siakam Trade– Toronto got three picks for Siakam. One was used to acquire Olynyk and Agbaji. One was used on Ja’Kobe Walter in 2024 (19th overall). He’s fine! And one was used to trade for Brandon Ingram (2026). It’s not a great return for a star player, but given how long they waited to do the deal, this wasn’t bad value.
Selecting Gradey Dick 13th overall in the 2023 NBA Draft: Dick had a decent sophomore season before regressing in a big way this year. While he might not be very good, it’s not like the Raptors whiffed on a bunch of other players to take him. Sure, they could have drafted Keyonte George or Jaime Jaquez Jr., but that’s hardly a franchise-ruiner. And Dick is still just 22 years old with plenty of time to figure things out.
Every Single Free Agency Signing: The Raptors free agency history in the 2020s is hilarious. They could not get anyone to come to Canada. Here is a list of some marquee names they added:
- Stanley Johnson
- Rondae Hollis-Jefferson
- Aron Baynes
- Alex Len
- Khem Birch
- Svi Mykhailiuk
- Otto Porter Jr.
- Will Barton
- Jalen McDaniels
- Dennis Schroeder
- Garrett Temple
- Bruno Fernando
Ujiri just wasn’t interested in free agency. None of those guys got big deals, none of them were any good. It’s remarkable. At least we know he won’t be counting on Plan Powder!
Objectively, this is a pretty poor run for any executive. Most of the moves made during this time didn’t work out, and it’s fair to wonder if Ujiri’s philosophy is still congruent with winning basketball in today’s game. However, when you consider the context of the entire post-title Raptors ecosystem, I think it’s easy to take a glass-half-full approach toward Ujiri’s next chapter in Dallas. Here, he has complete control with new organization, one with a generational superstar tailor-made for Ujiri’s sensibilities. If this doesn’t re-energize him, he’s probably got nothing left.
