The only thing missing was the champagne.
When the MLSE corporate jet arrived in Miami, the deal was finally done.
Masai Ujiri was going to stay with the Toronto Raptors and for the first time in nearly two years questions about the status of the team president could be put to rest and the focus could move firmly to the future.
Maple Leaf Sports and Entertainment chairman and minority owner and his right-hand man, Dale Lastman arrived in Miami to pick up Ujiri in early August to ferry him back to Toronto to sign a deal that would make him the richest executive in the NBA – if not all North American sports – but also connect him to the franchise in a way almost unheard of in the industry.
Ujiri isn’t charged only with nailing down contracts and digging up trades and hitting home runs on draft day, his role will continue to be all those things but also to raise the profile of the organization within the league and throughout sports globally.
It was a celebration of a negotiation that had been intense though amicable and the start of a new chapter in an ongoing story that is in its early stages.
The plan was to toast the deal on the flight back to Toronto for the final paperwork, but the champagne never made it on board.
It was an oversight, but perhaps the only detail that didn’t get covered in a comprehensive negotiation that began in early June and lasted nearly two months.
No matter. Ujiri was on the plane and the deal got signed. And in his first public comments since his contract was announced on August 5th; he confirmed that his plan is to see this through.
The exact terms of the deal have been vague and even after Ujiri’s press conference on Wednesday afternoon, they remain that way.
For example: What, precisely, does ‘vice-chairman’ – his new title in addition to president -- mean?
“It’s sexy, it’s cool,” was Ujiri’s eventual summary after speaking broadly about everything from his role helping grow the Raptors business internationally, to infrastructure upgrades locally to the Raptors and MLSE’s push to create more opportunities for the BIPOC (black, indigenous and people of colour) community.
But sometimes the spirit of the thing speaks louder than the details.
How long is Ujiri’s new contract for?
“Forever. Put pressure on Larry [Tanenbaum], here,” Ujiri said. “Forever, man. Forever. No, honestly, I’m not going to put out things there. I’m home, man. This is it. We’re going to try to win the best way that we can. It’s a commitment. I’ve always said that when you make that commitment, you make that commitment. That’s what I said eight years ago. I think we honoured it as a family. And that’s what we intend to do always.”
My best guess? Given the deal was announced as “multi-year” and “significant” and given that Ujiri has not hedged about Toronto being home, there’s no chance the contract is for three years or less. But given the rapidly changing business climate in sports, Ujiri would be unwise to lock himself into something like seven or 10 years. Just like the best players in the NBA, you always want to be in a position to negotiate again the time is right.
Does five years sound right? Seems reasonable to me. But even if we’re doing this dance again in 2026 it’s clear that Ujiri's heart is here.
The heavy lifting on the deal was done by Lastman and Ujiri’s advisor, Robbie Robinson of Pendulum holdings, who also advises former U.S. president Barack Obama. Tanenbaum and Ujiri began participating more directly in the final few weeks as the momentum for the deal grew.
The negotiation was challenging, for exactly that reason, Ujiri said. At 51 he was at a crossroads professionally and personally – Ujiri’s wife and two school-aged children were at the press conference; they decided not to risk the fussy factor of their infant son – and the next step had to be just right.
“I understood that this process was going to be difficult and that’s why I left it until the end of the season,” Ujiri said. “Negotiating is difficult, that’s what comes in the terrain. Me and my family really looked at this and you get different offers that come to you, but it comes a point where you have to weigh those options and what’s best as a family and for me. Everything we went through always came back to Toronto and what Toronto means to me as a city. I call it home. It’s home for me and my family. When it comes to negotiating, we just have to talk about some of the things that are not only important to me but are also important to the organization too. And you bring it together.”
Which is Ujiri’s task now. He’s got to bring it all together.
He’s been given the keys to the kingdom – or he’s earned them. Multiple sources have confirmed that there’s no ownership arrangement but in addition to a handsome salary believed to be among the highest in pro sports, there is likely some ‘equity-like' elements to the deal. According to executive compensation experts that could mean Ujiri earning bonuses based on revenues or even participating in the growth in the valuation of the company over the course of his deal. Given the revenues MLSE has enjoyed, not to mention the trajectory of NBA franchise values – $2 billion and climbing, even at the low end – Ujiri is in position to be richly rewarded.
But winning drives the bus. Tanenbaum is as low-key an owner as you’re going to find in the ego-driven world of professional sports, but it was hard not to notice the diamond-encrusted ring he wore from the 2019 Raptors championship as he looked on from the front row as Ujiri spoke.
“I said it from the beginning when I came here, we want to win in Toronto, we want to win another championship,” Ujiri said. “All that stuff [the 2019 title] is from the past. Yeah, you can celebrate and be cool about what you’ve done in the past, but the NBA is about now.
“We have to put ourselves in a position to win another championship. In some ways there’s unfinished business,” Ujiri said, alluding to the moment when he was inappropriately man-handled by an Oakland police officer as he made his way to celebrate after the Raptors eliminated Golden State in Game 6 of the NBA Finals at Oracle Arena in 2019, an incident that sparked headlines, lawsuits and marred what should have been a career-defining moment.
Tanenbaum nodded his head in approval of the message.
If Ujiri can get the Raptors back to that stage again it will be his greatest feat yet and will justify every penny and every perk and every freedom his new contract provides. He’s starting with a young team, largely unproven, and once more is faced with flying into the headwinds against superstars and super teams in a league that caters to both.
But he believes it can be done and the Raptors have given him a deal that expressed their full confidence that he can make history again.
“I want to celebrate properly one day when we win a championship,” Ujiri said. “… And it’ll happen, by the grace of God.”
There will be champagne then. You can guarantee it.