Many factors at play for Ujiri as Raptors contract decision draws near

The last time Masai Ujiri was a pending free agent, his next move was decided at a posh mountain retreat in Vail, Colo., a two-hour drive west from Denver where he was in the final year of his contract as general manager of the Nuggets.

He met there with Tim Leiweke, then the decidedly up-tempo chief executive officer of Maple Leaf Sports and Entertainment. At the time, Leiweke was in the midst of a lightning-speed makeover of the company that owned the Toronto Maple Leafs, Toronto Raptors, Toronto FC and a range of other holdings, but no championship trophies.

Leiweke’s contacts in the NBA and across the sports industry in North America ran deep, and he’d determined in the spring of 2013 that Ujiri was the person he needed to right the ship that was the Raptors, seemingly drifting aimlessly into mediocrity in what turned out to be the final days of former Raptors president Bryan Colangelo’s run with the club.

Ujiri — who had worked as a scout and assistant GM for Colangelo in Toronto before taking the GM position with the Nuggets — had led Denver to three consecutive playoff appearances and a franchise record 57 wins in 2012—13. He was a star on the rise.

“We talked to other people,” said Leiweke, who revamped the front offices of all three of MLSE’s clubs in his brief-but-impactful 30-month stint in Toronto. “But we had done our homework, and [MLSE chairman] Larry [Tanenbaum] knew him from before so that helped, but we were laser-focused on Masai.”

Nearly eight years later, that day in Vail remains the pivotal moment in Raptors history. The Ujiri-led team made the playoffs in 2013–14, starting a streak that should run to eight seasons in 2020–21, barring anything unforeseen. The list of franchise records and firsts under his leadership is endless, but features most prominently Toronto’s NBA championship in 2019.

But Ujiri is a pending free agent again. His eighth season with the team is also the final year of his current contract, and all signals are that he is in no rush to sign an extension.

The people he works for? They would have signed him yesterday if they could.

“I can promise you, it’s not [MLSE],” said a source with knowledge of the ownership’s thinking. “They’d have to be nuts not to [want to sign him]. It’s not like there’s a Plan A and a Plan B. There’s only Plan A, and it’s him.

“But he’s a very deliberate guy, and the kind of guy you have to respect his space.”

Ujiri has kept his intentions close to the vest, speaking publicly only in broad terms.

On Saturday, in his address prior to the opening of training camp, Ujiri said he’s extended the contracts for all of his leadership team with the exception of general manager Bobby Webster whose deal is all but completed.

“I think we are sealing it,” he said. “I would consider that done soon enough.”

But on his own deal he was far less definitive, citing that the logistics of seeing the team through the relocation from Toronto to Tampa Bay as a short-term obstacle, just as seeing the team through the pandemic and the restart was an obstacle before that.

The two sides haven’t talked in depth about his contract since February, according to sources.

“I think there’s just been so much that I know I’ve pushed it out ’til I think we get through a lot of this,” he said Saturday. “There’s just so much going on with this relocation and the focus, and I don’t want to be distracted that way.”

But would he anticipate a new deal being reached in the next few months?

“I don’t know what the timeframe will be,” he later added. “I go into this thing with a very positive mind and attitude. And we hope it goes that way.”

So as the clock starts ticking on the final year of his current deal and Ujiri’s future, the central question hanging over the team he’s built in his image is how, one way or the other, history will repeat itself.

Either Ujiri will work to the end of his contract and move on to his next opportunity as he did leaving Denver for Toronto, or he will sign with the Raptors again — he has already signed one extension back in 2016 — and continue a run that has cemented his place in the city’s sports lore.

He will be paid handsomely no matter what direction he chooses.

In conversations with other NBA executives and other league insiders, the consensus is his track record — his teams have made 10 consecutive playoff appearances and averaged more than 50 wins — and league-wide profile, combined with the leverage he has, will almost certainly make him the highest-paid executive in the league for now and into the foreseeable future. The bidding will start at $12 million a year.

“Masai has gotten to the point where he’s maxed the market as it relates to someone in his position,” said one well-positioned league insider. “As far as a front-office person is concerned, he’s going to make the most money that a front-office person has ever made, and he’s probably going to be able to hold that, where no one is going to be able to usurp that number.”

The bigger question is what will it take for MLSE to convince Ujiri to stay in Toronto — or at least, why has he been hesitant to sign a deal so far — and for what reason would he want to leave?

In that case, how he got here in the first place might be instructive. Leiweke quickly understood what appealed to Ujiri was more than money or security — it was the ability to match his ambition.

“We just talked about life first. I got to know him and got to know his vision on what he would do differently if he were in Toronto. We spent a lot of time talking about Giants of Africa and Basketball Without Borders and how we could help. We talked a lot about the relationship between us and talked an awful lot about what it would take to win.

“And he came back and said: ‘Here are the things that are important to me.’”

Ujiri had a list. Looking back on it captures the size of the mountain he has been able to move in making the Raptors one of the most successful and respected organizations in the NBA over his tenure.

According to Leiweke, the list included: Helping him broaden his charity work; constructing a dedicated practice facility; starting a locally based G-League franchise; hosting the NBA All-Star Game; and Ujiri having unfettered control of basketball decisions. It all led to the No. 1 item: winning a championship.

“And I sat there in that meeting and said, ‘Here is how we’re going to do this.’ Done. ‘Here’s how we’re going to do that.’ Done, done and done. And went down the list and I showed him how I would get everyone on the same page,” said Leiweke.

“I knew one of the strengths we’d have as an organization is our ability to immediately show him a plan of action for how we were going to execute his vision. It was very refreshing for him.”

The deal was reached in principle before Ujiri headed back down the mountain to Denver.

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Maybe that’s the best way to look at what might keep Ujiri in Toronto: What mountains does he want to move next, and who is going to help him do the heavy lifting?

What’s on his list now?

Regardless of the details, if the MLSE board thinks Ujiri might be prone to easing up on the gas after a long stretch of unprecedented success, it would be a serious miscalculation, in Leiweke’s mind.

“I’m not going to get involved in any speculation with what’s going on with them. That’s a loss leader opportunity for me for someone to get pissed at me,” Leiweke said. “But I’ll say this about Masai: He challenges himself every day. He loves a challenge. The risk [for MLSE] is that there are great challenges out there in this league.

“[And] Masai loves that challenge. Tell him ‘no’ and that’s where Masai will go. Tell him he can’t do it and that’s where Masai will land,” Leiweke said. “The more impossible the challenge, the bigger the dream, the more Masai will want to do it, and that’s the challenge for Toronto.

“What they’ve accomplished now, that’s not good enough for Masai. He has to have the next five things. He’s going to want to have a higher place to go to, a greater challenge, and that’s just the way the guy is wired, and that’s why he’s so successful.”

What assurances might Ujiri be seeking in a new deal?

There have been changes at MLSE — owned by BCE and Rogers, each with a 37.5 per cent share, while Larry Tannenbaum owns the remaining 25 per cent — that might give Ujiri pause before committing to another long-term deal.

Former Bell Canada chief executive officer George Cope retired from the board last summer. Cope and Tanenbaum’s unwavering support meant that Ujiri could proceed confidently, knowing his vision for the Raptors would hold sway. While there’s no indication that will change with a new board configuration — Rogers deputy chairman Melinda Rogers-Hixon and Bell CEO Mirko Bibic are the new faces — that theory has yet to be tested.

If the board shares Ujiri’s passion to take the Raptors to even greater heights, then all good. But any whiff of complacency in a league where the Golden State Warriors have committed to a $175-million payroll and another $82-million in luxury tax after a 15-win season could potentially push Ujiri to keep looking for his next opportunity.

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Other reasons? It’s hard to imagine any of them being deal breakers but there have been some minor issues. Some close to the situation say that a report that the Washington Wizards were preparing a significant offer to hire him away from Toronto broke the night the Raptors won the championship in Oakland, “rubbed some people the wrong way.” Similarly, MLSE’s lack of haste in reaching out to Ujiri immediately after the title win provided Ujiri justification to slow play his hand keeping the pressure on while keeping all of his options open. There have been no meaningful negotiations since.

Ujiri said this past summer that he wanted to wait until his top lieutenants were rewarded before he sat down to talk, but with those deals done only his deal remains and now the clock ticks louder.

His bosses would love to have Ujiri back, and the door will remain open whenever he chooses to walk in and sit down. Until then, Ujiri is probably best served taking his time. The only problem?

Opportunities where Ujiri could make 10 figures while enjoying almost unlimited say over the basketball operation — “No one questions a single thing he does,” says one source. “He tells them out of respect, but that’s all.” — and having the freedom to pursue his other passions are few and far between.

“The list of teams that could afford him is very, very short,” said one Eastern Conference executive. “The Knicks, Brooklyn, Chicago, maybe Miami … the L.A. teams, Golden State — none of those jobs are available right now.”

As one source said to me: “In Toronto, he’s treated better than he would be treated in any other market where the expectations would be a lot higher in terms of his whereabouts and his presence. If he went to New York, would he have the autonomy to go to Africa for three weeks and no one knows where he is and that would be okay? No. Maybe he would be afforded that on a honeymoon basis? But not after that.”

Said another: “There may be places where Masai has as much flexibility as he does in Toronto, but he can’t have more. He does whatever he wants.”

So what could be Ujiri’s next move?

One possibility could be ownership. A theory that some league insiders have put forward is that Ujiri is waiting for the right opportunity to join a new ownership group — maybe even in a secondary market — where his cache and track record could be recognized with equity in a new venture. Even a five–per-cent piece of a franchise worth $2.5 billion would be significant.

And while MLSE would likely be willing to exceed any offer Ujiri might get around the NBA, a business with two publicly traded primary shareholders might have a greater challenge carving out an ownership stake, although there are other ways to mimic equity in high-end executive compensation packages.

Another route to ownership could come through expansion. The NBA hasn’t added a franchise since 2004, with owners reluctant to divide their lucrative revenue pie any further than the existing 30 teams. Given the hit the league has taken in the pandemic, that reticence might change simply due to the expansion fees.

“Trust me, the league will expand,” said a league insider.

Is it worth noting that Leiweke is the chief executive officer of the ownership group that is bringing the NHL to Seattle in a newly renovated arena, the former home of the Supersonics?

“The NBA has a hole to fill, and if you do two expansion teams, that’s $4.5 billion. Divided 30 ways, everyone gets $140 million,” said Leiweke. “Ironically, that is a very, very similar number to the losses in 2020–21.”

But in any scenario, expansion is years away, and Ujiri’s contract has only one more year to run. If Ujiri were to head up a group seeking an expansion team, he’d have to find something else to do in the meantime.

Other options? His interests in politics and social change run deeply, but roles in those areas don’t typically come with 10-figure paycheques.

The NBA’s growing interest in Africa would also seem like a fit for Ujiri, but — again — there isn’t a job available that would match the profile and money he can command in the league now.

His friendship with Barack Obama could bear fruit as the 44th U.S. President could be looking for proven leaders to help him with his entrepreneurial plans, but anything like that would likely be a sharp turn from Ujiri’s expertise in basketball.

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Add it up and maybe Ujiri will continue doing exactly what he’s doing right now: wait things out while surveying the landscape for the next opportunity. He can be confident that one of the best jobs in sports will remain available to him for as long as he wants it, whenever he chooses to commit.

“He knows that [MLSE] desperately want to sign him. I believe [they] are going to sign him, but you never know for sure,” said the source close to the MLSE board. “[But] there’s no hold up on their part.”

Said one league insider: “I don’t know what the next step is, and I will tell you — I don’t think Masai does either, otherwise he’d be positioning himself for it.”

So perhaps a compromise will win the day? Rather than a long-term commitment, Ujiri could make like LeBron and take a shorter deal that helps him stay flexible should things change.

But when the two sides do sit down to negotiate, the finer points won’t be money, those in the know expect.

Instead, it will be details that allow him maximum flexibility now and in the future — the ability to interview for other jobs without having to gain permission, or softer parameters around non-compete clauses if he does leave.

In the meantime, it’s up to the leadership at MLSE to identify ways that they can make sure the best leader the organization has ever had remains challenged and engaged and convinced the ownership is prepared to match his drive and ambition.

“The thing that’s unique about him is he’s always going to push himself and he’s always going to have the next step, next phase, next series of accomplishments, and he’s not going to rest on his laurels, and it’s never just about the paycheque,” said Leiweke. “He’s going to want to continue to be very dominant as an organization, and he’s going to want to be one of those franchises where players want to come play for that franchise, that marketplace and for Canada.

“The most important thing for him is: Is he going to have a partner that’s going to push as hard as he’s going to want to push and get things done?”

Eight years after seeing his future in Toronto from the mountains of Colorado, Masai Ujiri is still looking for his next horizon.