Why confidence is mounting that Raptors can re-sign Masai Ujiri

Toronto Raptors President Masai Ujiri speaks to media. (Frank Gunn/CP)

The season is over and the time is now.

The largest single question looming over the Toronto Raptors will be answered soon — not in the coming days, necessarily, but almost certainly within weeks.

With apologies to Kyle Lowry, Raptors president Masai Ujiri is the franchise’s No. 1 priority in free agency. And after pushing aside multiple invitations to discuss his future with the club that have been simmering since the champagne was still wet on the floors of the visitors’ locker room at Oracle Arena in June of 2019, he can’t delay things any further.

“He’s always said at the end of the season he’ll start communicating [on his contract],” said one source with insight into how Ujiri is expected to approach the process. “He feels like he owes it to MLSE to think of them first.”

There is a mounting confidence that there is a clear path for Ujiri’s return, and there will be a good-faith negotiation to find common ground on a deal that will extend the Raptors president’s tenure with Maple Leaf Sports and Entertainment from eight years until as far into the future as he wants to stay.

It’s not like MLSE has a plan B to replace the person more tightly woven into the fabric of the franchise than any player.

Their position is straightforward. There are no tactics or posturing.

“They love him, and they believe in him,” said a source close to the MLSE board. “He’s won them a championship and they believe he’s going to win them some more.”

Can a deal be done? Optimism is increasing.

“Masai doesn’t share a lot; he’s very private and strategic in his own way,” said the source close to MLSE. “But if you were asking ‘Are they going to sign Masai?’ I would put it at 95 per cent yes.”

That’s the view of an informed handicapper, it should be stressed, rather than something based on any indication given by Ujiri, who has played his cards close to his chest since the first bombshell about his future landed in the moments after the Raptors won the title over Golden State, when it was reported the Washington Wizards had pursued him to run their organization, offering an ownership stake as enticement.

And there is still that five percent, which allows for a lot of room for ‘what ifs’ until a deal is signed.

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In terms of timing, it is believed that, pre-pandemic, Ujiri’s contract ran until June 30, but since the entire NBA calendar has been pushed back by about six weeks, there is likely some flexibility on that. There is even the possibility of extending the existing deal while terms of a new one are being finalized.

But given the significance of the Raptors’ off-season — with a high lottery pick in play; franchise icon Lowry heading to free agency; and the potential to have significant cap space to use — getting the Ujiri question resolved is at the top of the agenda.

For logistical purposes, the draft is July 29 and free agency begins on Aug. 2, but a lot of groundwork is laid well in advance of those dates. The club would benefit from certainty, and after giving Ujiri the space and time he wanted, conversations about his future with the team will be starting imminently.

As of late last week, specific times and dates to meet hadn’t been worked out. But after Ujiri finishes tying up loose ends in Tampa this week he is expected to return to Toronto ready to talk, and MLSE chair Larry Tanenbaum and the rest of the ownership group will be eager to listen.

And while the ball remains in Ujiri’s court, there is good reason to give good odds, in part because Ujiri’s hardly given the impression he’s on his way out the door.

There is a sense that Ujiri’s been more forward looking and engaged in recent weeks than at times over the Raptors’ draining and irregular regular season, according to those who have had dealings with him.

Certainly general manager Bobby Webster has more than ever become the first point of contact, which hasn’t gone unnoticed around the league, and having his staff grow into their responsibilities has always been one of Ujiri’s goals. Whether that’s being a good leader empowering his staff or laying the groundwork to leave without unnecessarily disrupting the Raptors business is something that league insiders have speculated about.

But as the Raptors’ critical off-season rounds into view, Ujiri is giving the impression he plans to be in the thick of it.

“We talked about winning and winning another title with the Raptors,” said one player agent who met with him recently. “He seems like he’s in a really good place.”

He’s been more active communicating with players, both in-person and via text, according to another source.

Certainly those that have gone to battle with him want to stay the course.

“He’s been the focal point of everything that’s Toronto Raptors ever since I’ve been here. Kyle Lowry is obviously the greatest Raptor of all time, and No. 2 might be Masai,” Raptors point guard Fred VanVleet said on Sunday. “He challenges every player and he rewards most of the players when you do what he asks you to do. He paid me twice so you’ll never hear me say nothing bad about him, and obviously we’d love to have him going forward…. He’s shown no signs of anything other than commitment towards us throughout this entire year, so obviously he is a part of what we think going forward, but contracts are contracts and you gotta negotiate. We’ll see where he ends up, and hopefully he’s back with us.”

Raptors head coach Nick Nurse was signed to a lucrative extension by Ujiri during the off-season a year ago, and the 2020 NBA Coach of the Year who Ujiri first hired as an assistant coach out of the G-League eight years ago wants that relationship to continue.

“All I know is I think we make a really good team,” said Nurse. “And I hope that team stays intact, and I enjoy working for him every day…. He thinks and talks in terms of championships.”

Ujiri and MLSE have met only once about his future, and it was back in February of 2020 when reports connecting him to the New York Knicks were swirling. That job was eventually filled by Leon Rose, and Ujiri has since said only that he would discuss his next contract with the Raptors at the end of the 2020–21 season.

So why put the chances of Ujiri returning so high, given he’s waited this long to become a free agent?

His relationship with Tanenbaum is strong, and they communicate regularly; his connection with Toronto is real; his job offers both opportunity and flexibility to pursue other passions close to him, such as his foundation work in Africa; and the Raptors are determined to keep him.

“There is nothing he can get somewhere else he can’t get here,” said the source close to MLSE. “His family loves Toronto. Toronto loves Masai. They’re going to pay him a lot of money. Like, why would he [leave]?”

Ownership, maybe? That’s the peak of the NBA food chain and something that is unlikely to be available with MLSE given the breadth of properties it includes, and the complexities of the ownership structure that has two public companies as primary shareholders. A deal can be structured to mimic shareholder value, according to sources, but actually having equity in an enterprise worth multiple billions is unlikely.

But ownership stakes aren’t exactly low-hanging fruit, and teams aren’t routinely up for sale, so it’s not likely going to be a make-or-break issue.

By becoming a free agent rather than signing an extension, Ujiri has allowed the market to play out to see if a next-best opportunity would materialize, but the number of NBA jobs as good or better than running the Raptors are few and far between, especially given there is no chance MLSE is going to let money be the reason Ujiri leaves.

Running one of the league’s glamour franchises — the New York or Los Angeles-based teams, say, or maybe Miami — could be attractive, but those positions are filled. Even a team like the Philadelphia 76ers conceivably could have been an option coming off a disappointing 2019–20 season, but their needs were urgent and they snapped up former Rockets president Darryl Morey on a deal believed to be worth $12 million a year, which will be the starting point for any Ujiri negotiations.

Could the Wizards resurface as a possibility? Tommy Sheppard is in the last year of his contract as general manager, but the Russell Westbrook trade has them trending positively, and Washington owner Ted Leonsis has typically shown considerable loyalty to his staff in both his NHL and NBA operations.

There is also the matter of the revenue hit that all teams have taken during the pandemic. The Wizards have never been one of the NBA’s big spenders, and it seems unlikely that this would be the off-season they would pay to make Ujiri the richest executive in North American sports.

 
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If Ujiri is determined to find a different opportunity, his main play at this point may simply be taking time off. He’s not a man without interests or connections — a quick phone call to his pal Barack Obama could land Ujiri on an engaging project or two, undoubtedly.

He’s often told people close to him about his fascination with European soccer — his first love growing up in Nigeria — and the recent Super League fiasco proves that there is a demand for more forward-thinking leadership at the top of the sport. Someone with Ujiri’s resumé and network in North America, Europe and Africa would have to be taken seriously, but it might take time for the right fit to emerge.

A more tangible option might be NBA expansion and the opportunity it could provide to become part of an ownership group.

The obvious connection is with Tim Leiweke, who recruited Ujiri to the Raptors in 2013 when he ran MLSE. Leiweke is now co-founder of the Oakview Group, who helped land the NHL’s Seattle Kraken expansion franchise and redevelop Key Arena, and whose brother, Tod, is one of the Kraken’s owners.

It’s widely believed the NBA will expand for the first time since rounding out to 30 teams in 2004 partly to recoup losses from the pandemic. Returning to Seattle as part of the process is almost a given (with Las Vegas as the other likely city) now that the arena issues that led to the Supersonics leaving for Oklahoma City in 2008 have been resolved.

“If there is expansion, he’s definitely going to get his opportunities,” said one league insider.

But there is no timetable for that, and typically there is a minimum two-year lag between franchises being awarded and play beginning. And given the league hasn’t formally announced any plan to expand, it makes little sense for Ujiri to remain on the sidelines passing up an opportunity to be the highest-paid executive in the sport while waiting for a day that could be years in the future.

A shorter-term deal with some flexible language included could offer the best of both words, and the Raptors likely won’t balk at that.

“They’re going to try to sign him for as long as they reasonably can, [but] if they have to sign him for less [years] they’ll sign him for less,” said the source close to MLSE. “They don’t have a lot of leverage. They want him. If he wants [a shorter deal], what are they going to say, no?”

The answers will be forthcoming soon enough.

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