TORONTO — Masai Ujiri’s signature on-camera moment during his tenure didn’t come in Oakland when Adam Silver presented the franchise the Larry O’Brien Trophy. Rather, it came before that season ever started.
On media day before the 2018-19 season, Ujiri delivered his instantly viral motivational speech, encouraging Torontonians to believe in themselves and their city. Perhaps lost to some memories: The response was one question removed from a reporter asking him about the challenge of selling the Raptors, the city and the country to Kawhi Leonard, one of the NBA’s best players. With the exception of the heights of Vinsanity, the Raptors never truly had a superstar at the peak of his powers. They certainly had never been able to acquire one in free agency. Sometimes, they couldn’t even retain their own home-grown stars.
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While Ujiri bristled at the notion that the perception of Toronto could hurt the Raptors at the time, it ended up impacting him on a personal level.
“The day we won the championship, the only thing I was thinking about (was), ‘Are we going to re-sign Kawhi?’” Ujiri recalled at his end-of-season press conference on Wednesday. “There’s no time to enjoy it.”
His incident with a Sheriff’s deputy in Alameda County contributed to this too, but Ujiri said he doesn’t believe he enjoyed his professional pinnacle as much as he should have.
“I guarantee you I’m going to enjoy (the next title),” Ujiri said. “And I guarantee you we are going to win here.”
It’s a bold, if familiar, claim, given Ujiri’s Toronto Raptors backed up a 25-win season with 30 victories in 2024-25. They have a 7.5-percent chance of winning May’s Draft Lottery and the right to pick projected franchise fulcrum Cooper Flagg. Their young star, Scottie Barnes, advanced as a defender and leader this year, but his potential as an offensive, floor-tilting stud took a huge hit.
In a way, Ujiri is back at a podium from the past, but not the one he sat behind in 2018. Rather, it’s 2013, when Ujiri became Raptors president, all over again, with Ujiri trying to figure out how to create a winner in a place where the stars aren’t going to come to him.
Masai on the team’s culture… 💯 pic.twitter.com/1LjFlQvsKl
— Toronto Raptors (@Raptors) April 16, 2025
If Leonard taught him anything, it’s that you can do everything right — prioritize a player’s health and win a title — and still not get the outcome you could argue the Raptors earned.
“At the end of the day, you have to acquire talent,” Ujiri said when he was asked about the surprise midseason acquisition of Brandon Ingram, which came with a three-year, $120-million extension, after he said last year that he was ready for a multi-year rebuild. “We have to do it in a unique way in the market that we’re in and we’ve got to jump on opportunities that come our way, sometimes after we really study them.”
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Implied, but not said out loud: Ingram is the type of player the Raptors wouldn’t be able to get to come to Toronto in free agency, even if they had the financial flexibility to do that, which they wouldn’t have had in the absence of the trade. In an effort to amass enough talent to eventually put the Raptors in a position to chase a championship again, Ujiri cannot afford to wait for the ideal player to hit free agency or demand a trade. The Raptors have been in conversations for star players over the last few years, and the interest has not always been mutual. It’s true: All these years later, some players still don’t want to come to Toronto.
Accordingly, Ujiri has to stack talent, and Ingram’s acquisition cost was low enough that he felt the opportunity cost — the Raptors now have one less first-round pick to throw in a bigger trade and are in a dicey financial situation for a 30-win team — was worth it.
We’ll see. It’s a big bet on an injury-prone player with at least some overlap with the team’s other two top scorers. It’s a big bet on his coach, Darko Rajaković, who has been pristine in getting his players to buy-in to his message but will now need to get Ingram to eschew holding the ball, the biggest criticism of his game.
Most strikingly, it’s practical. It is no longer daydreaming about making the next Kawhi trade, although perhaps a similar opportunity will present itself. It is no longer about setting the Raptors up for a run at Giannis Antetokounmpo in free agency as it was a few years back, although Ujiri certainly wouldn’t be shy if he hit the trade market. He’s hoping the Raptors get lucky on lottery night, but isn’t banking on it, which is perhaps why the front office was quite as angsty as the media and fans were with every win this year.
Aside from hoping that the NBA’s European push results in Toronto becoming a more desirable market — Ujiri’s predecessor, Bryan Colangelo, had the same hope almost two decades ago — Ujiri is trying to make marginal gains, however he can. This past season, the Raptors were hopeful those gains came from the draft, with Ja’Kobe Walter, Jonathan Mogbo, Jamal Shead and Jamison Battle showing signs they could be viable rotation players on a good team. Given how expensive the Raptors’ starting lineup is, that supplementary roster-building is huge.
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It seemed as if Ujiri wanted to take a victory lap for potentially nailing a weak draft, as the Raptors’ developmental reputation has come under fire since the championship, but he mostly played it cool.
“I was really happy with the way these guys played and hopefully their development comes up more and more,” Ujiri said. “Yeah, we tried to attack the odds in the lottery and see what we can do. It’s a good draft. And honestly, wherever we fall, we feel very confident. Our guys have done a lot of work all year. We’re extremely excited.”
The Raptors seem hemmed in by their financial situation this offseason, with little to do beyond making their picks. Ujiri seems excited by the prospect of exploiting whatever opportunities arise. Although more muted (all things are relative) than usual, Ujiri seems energized by the Raptors’ complicated positioning.
Obviously, Ujiri wants his championship moment back. Who wouldn’t? Maybe, he wants his reputation as one of the league’s savviest organization builders back, too.
(Photo: Kevin Sousa / Imagn Images)
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