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Why Ujiri’s bombshell exit felt inevitable for Raptors

June 28, 2025
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He is not going to win again in Toronto. 

Winning in Toronto has been Masai Ujiri’s mantra almost since he arrived like a molten ball of kinetic energy prior to the 2013-14 NBA season. 

And with the champagne barely dried in celebration of the 2019 NBA championship run he was instrumental in orchestrating, delivering an epic and unforgettable climax to what was then a six-year run of unprecedented success for the Toronto Raptors, the mantra became: ‘We will win again in Toronto.’

The pledge only became more urgent since he signed a five-year contract in the summer of 2021 and the team’s on-court success receded into the rearview mirror. 

In what were his last public remarks in his capacity as Toronto Raptors president and vice-chairman, Ujiri said at his post-season media availability that his goal was to win, in part because the pure bliss that should have accompanied the 2019 championship was interrupted — both by a courtside confrontation with a law enforcement officer working security at the Oakland Coliseum that triggered a lengthy legal battle and the imminent departure of then-Raptor Kawhi Leonard in free agency. The Raptors’ title defence was then interrupted by COVID. 

Ujiri wanted to win again, but to feel it more this time, to revel in the joy that so many millions of Raptors fans were able to bathe in during those magical two months six years ago last week. 

It’s not going to happen. The Raptors may, or may not, win again in Toronto, but Ujiri won’t be part of it.

On Friday morning, in news that was somehow at once a bombshell and inevitable, MLSE — the Canadian sports giant that owns the Raptors, Toronto Maple Leafs of the NHL and Toronto FC of MLS, along with other sports holdings — announced that the Raptors had parted ways with Ujiri after 13 seasons. 

It was a bombshell because ‘parting ways’ with your top basketball decision maker less than 12 hours after the NBA Draft was completed and barely three days before the start of free agency is not the normal time for basketball executives with a year left on their contract to be sent on their way. 

“You knew it was coming, there were rumblings,” said one long-term NBA insider. “But the timing was weird.”

Sources close to the Raptors described a ‘business as usual’ atmosphere in the build-up to the draft Wednesday and Thursday. The first person to speak with Collin Murray-Boyles, the forward from South Carolina that the Raptors selected with the No. 9 pick, was Ujiri via FaceTime. An agent said he was talking with Ujiri about future business in the wee hours of Friday morning. “He didn’t sound like a guy who was going to lose his job in the morning.”

Another agent with players the Raptors were considering taking in the draft, and with players on the current roster, said he was talking with Ujiri in the lead-up to the draft.

“It’s shocking,” he said. 

Or just proof that Ujiri can keep a secret. 

The timing was explained by MLSE president Keith Pelley at his media conference Friday shortly after the news broke that it was the result of a mutual decision based in part on Ujiri’s desire to see the draft through and avoiding unnecessary disruption and distraction, and that the decision had been made sometime before Friday.

“Masai and I spoke over a month ago and he asked if a change were to happen, that it was post-draft. And that made the most sense — not to disrupt the draft process,” said Pelley, praising Ujiri’s integrity for keeping the news under wraps during the process. “We were holding the ninth pick, a top-10 pick. And of course, not only (is the draft) Masai’s area of passion, his area of expertise, he’s prolific when it comes to the draft. And we were grateful to have him as a person with (general manager) Bobby leading our draft.”

And going forward, given the Raptors roster and payroll situation — tight against the luxury tax threshold, and with only a few roster spots to play with, likely ticketed for minimum contract filler — there likely aren’t any significant basketball decisions looming in the short term, so even with free agency pending, Ujiri leaving on the eve of it likely won’t be an issue. 

The inevitability of the decision? The why?

There are a number of reasons why Ujiri’s tenure with the Raptors was coming to an end, with only the timing — the ‘when’, not ‘if’ part — looming as the primary question to be answered. 

But perhaps the simplest reason is that forget about the Raptors winning again in the future, the Raptors weren’t winning now and haven’t done much of it for the past five years. 

Any other executive coming off five seasons with one first-round playoff exit to show for it, and two years of ‘tanking’ with only the ninth overall pick as the prize for the pain, and having traded away the Eastern Conference Finals MVP in Pascal Siakam and an All-NBA defender in OG Anunoby — a year too late, in retrospect, most would agree — only to watch them thrive on playoff teams, would have some explaining to do heading into a contract year. 

Ujiri had a massive amount of credibility and equity built up over the Raptors’ performance from 2013-14 when — in addition to their championship — they went to the playoffs seven straight years, won nine playoff series and set franchise marks for wins four times. 

It’s why he was able to land one of the most lucrative executive contracts in all of sports in the summer of 2021: A five-year deal with a base salary of $15 million (USD), along with a long-term incentive plan tied to the annual increase in franchise value, among other benefits, per multiple sources. 

With only one year remaining on that deal, it was going to be — as one source put it to me — unlikely that Ujiri would be in a position to command an extension, let alone a raise when his deal was up. 

With the writing on the wall, it made more sense for all concerned to ‘part ways’ now, rather than have the issue hanging over the team for the next 12 months.

As for what it means for the Raptors in the short-term, it will be status quo, or as much as is possible without the band’s lead singer. 

Raptors general manager Bobby Webster and the rest of the front office have had their contracts extended, although — per a league source — Webster’s extension is on the shorter side. 

One of the twists emerging Friday was that MLSE would begin a search for a new president immediately, engaging with Los Angeles-based CAA Executive Search in the process, with Webster also being interviewed for the president’s job. Pelley didn’t hire a president to replace former Maple Leafs president Brendan Shanahan, whose contract was not renewed after the NHL season, but according to sources, that was in part due to Pelley’s relative comfort level and familiarity with the inner workings of the NHL. 

The NBA is a different industry, and Pelley — according to sources — decided that another layer of leadership with specific NBA expertise would be the wise path.  That could end up being Webster, with perhaps assistant general manager Dan Tolzman bumping up to the general manager role, or it could be a new president altogether. 

“We are hiring another president. Whether that’s Bobby is to be determined. But we’re not hiring a president and a general manager. We’re hiring a president. We will have a general manager,” Pelley said. “… We’re looking for an experienced, prominent, strong, successful personality.”

Raptors fans know all too well what a president with an ‘experience, prominent, strong, successful personality’ profile looks like. Ujiri checks all those boxes and then some. 

He used those traits to build a championship team. He used them back in 2013-14 to almost instantly shed one of the most moribund periods in Raptors history when he took the stage outside what was then the Air Canada Centre and dropped the ‘F-Brooklyn bomb’ on the eve of the playoffs, minting Jurassic Park. 

He used them when he was able to convince Kyle Lowry that his best interests were to embrace being in Toronto and leading the team he was already on, or in his determination to use the platform the Raptors and the NBA provided to advocate for African development, for community development here in Toronto and elsewhere in Canada. He was as comfortable talking to past presidents (he calls his pal, former US president Barack Obama, ’44’) as he was 19-year-olds on their first day in the NBA; as at home addressing the United Nations as he was sitting in a cramped bleacher seat scouting future second-round picks. 

Everything comes to an end, and Ujiri’s 13-year run in Toronto — the profoundly great, the not-so-great and the unlucky — wasn’t bound to last forever. But it’s over now, and it will be someone else — walking in a very long shadow — charged with figuring out how to win in Toronto again.



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Tags: bombshellexitFeltinevitableRaptorsUjiris
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