Stress over Masai Ujiri’s future with Raptors just beginning

Tim and Sid breakdown the NBA trade deadline as it pertains to the Toronto Raptors, including the New York Knicks hiring of Leon Rose as president of basketball operations, and why fans shouldn't celebrate just yet.

For the moment, there is time to exhale, breathe deeply, and exhale again.

The Toronto Raptors were never likely to make a significant move before the NBA trade deadline passed Thursday afternoon.

But now the focus can be entirely on the group at hand, the one that has a chance to win a franchise-record 60 games, the one that has the third-best record in the league.

From Toronto’s point of view the biggest deal of all is the one that’s not going down, at least for now.

The New York Knicks no longer have a job opening with Masai Ujiri’s name on it.

All indications are that the Knicks have opted to replace former president Steve Mills with prominent player agent Leon Rose.

The move should temporarily quell the fevered speculation around the possibility of Ujiri bolting – either to the Knicks, where there no longer appears to be an obvious job available, or anywhere else at the moment.

That Knicks owner James Dolan was so easily distracted from his widely-reported determination to lure Ujiri to dig New York out of 20 years of dysfunction is telling.

Basically Dolan is going to Dolan.

“You can give him all the advice, all the guidance, all the background and he’s still going to do what he wants to do. He moves to the beat of his own drum,” a source familiar with the Knicks’ search told me Tuesday when the rumours bubbled up again.

Even if the wheels were being greased to ease Ujiri to the Knicks at some point – and multiple league sources have confirmed to me that the Raptors executive has seen the Knicks as a viable destination, depending on timing – there was always the possibility that Dolan would veer into another direction, and he did.

It probably didn’t help that Larry Tanenbaum — Raptors minority owner and chairman of the NBA board of governors – was not about to make it easy for the Knicks to poach the architect of the Raptors’ success.

Whether that involved Tanenbaum appealing directly to Dolan or to NBA commissioner Adam Silver or both, the sense is Raptors ownership was emphatic: there would be no cooperation from them to make Ujiri’s exit at any time in advance of the natural end of his contract in the summer of 2021 any easier.

Faced with the possibility of massive demands for compensation, obstacles to granting permission to talk, and the message that the tampering radar would be on full, Dolan has apparently chosen the bird in the hand rather than waiting to see when Ujiri could be flushed out.

Back in Toronto there remains some toothpaste to push back in the tube, however.

The immediate question is if and when Ujiri will sign a new deal with the Raptors – the only measure that would put to rest speculation on his long-term future with the team he is poised to lead to the playoffs for the seventh straight season, this time while defending an NBA title.

My understanding of the situation is that though there have been some preliminary discussions between Ujiri and the ownership group at MLSE, nothing has changed in the past month regarding the Raptors president’s desire to not address his contract status until the summer of 2020 at the earliest and maybe all the way to 2021. That doesn’t mean MLSE won’t get a chance to pitch him on a new deal, but there’s no guarantee Ujiri won’t push his decision as far out as possible.

Why was ownership slow off the mark in initiating contract talks with Ujiri?

That he had two years left on his deal, a championship bonus to spend and the principals were all embarking on a compressed, post-championship summer schedule is the best explanation I’ve come up with.

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Ujiri certainly has no incentive to push things along in the meantime. The longer he waits the more his leverage will build. Not only will he be entering the final year of his deal in 2020-21, all his top basketball staff are in the same boat.

Not that he should need it, but it’s impossible to navigate NBA waters as successfully as Ujiri has over his career without understanding the benefits of negotiating from a position of strength.

But considering how strong a relationship Ujiri has with Tanenbaum (“he’s like a son,” the Raptors chairman said in the championship dressing room back in June when reports of the Washington Wizards’ play for Ujiri surfaced), it’s interesting to speculate about what might be holding Ujiri back even now with the opportunity in New York apparently past.

One clue could be the future status of the eight-member MLSE board and what kind of company Ujiri would be signing up to spend the prime years of his career with.

Since being recruited from the Denver Nuggets – where it should be pointed out, Ujiri passed on opportunities to sign an extension and worked through to end of his contract before leaving for Toronto – in 2013, Ujiri has enjoyed a charmed corporate existence.

The Raptors are owned by MLSE, which in turn is owned by Tanenbaum (25 per cent) and Rogers Communications and BCE (37.5 per cent each), and which owns the Maple Leafs, Toronto FC and Scotiabank Arena among other properties.

As it relates to the basketball operation, Ujiri’s reporting structure has been fairly streamlined.

Tanenbaum could always be counted on to be in his corner. Tanenbaum was in the bidding to bring the NBA to Toronto in the early 1990s. The 2019 title was a dream come true. He has always been all in.

Over the years, Bell chief executive officer George Cope became a staunch ally too. Cope played basketball at the university level and is a passionate and knowledgeable NBA fan. The potential for basketball’s growth in Toronto and Canada didn’t have to be explained to him. Moreover, as one of the driving forces behind the Bell Let’s Talk Day initiative to raise funds and awareness around mental health, he could appreciate Ujiri’s passion for his Giants of Africa Foundation.

With Tanenbaum and Cope in his corner, Ujiri could feel confident that his vision for the basketball operation could unfold relatively seamlessly. The Raptors’ new practice facility, the addition of the G-League franchise, a commitment to reward staff and to go into the luxury tax when needed are all evidence.

But Cope retired as Bell CEO last month and his term on the MLSE board is up this summer.

Will the incoming Mirko Bibic replicate his predecessor’s basketball passion?

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Given that the Rogers side of the ownership group haven’t been as directly tied in with the day-to-day operations of the team, it makes sense that Ujiri might be looking for reassurances that the new-look board of directors will share his vision and passion, neither of which come cheap.

For the first time since Ujiri came to work in Toronto there is some uncertainty.

In that same vein, the status of Tanenbaum could be worth watching.

Tanenbaum is 75 and in robust health, but it’s fair to wonder if his influence within MLSE is forever. Is there a timeline during which a change of control could be required? What would MLSE look like then?

More broadly: after a period of aggressive expansion and a fairy tale championship, you can assume Ujiri would want to feel confident about MLSE’s future ambitions and their willingness to compete in a world where payrolls crack $200-million and beyond.

Do they want to stand out? Not just in the NBA, but beyond?

Suggesting that Ujiri would be satisfied working for a nice Canadian NBA franchise that won a title once and is content to string together a few winning seasons here or there is to suggest you don’t understand the man.

And on that subject, how much do they really value the charitable work he does? Enough to make a donation and provide some back-office logistical support as they do now?

Or enough to help him make it as big as Ujiri wants it to be? To have a presence throughout Africa, rather than a handful of countries? To help grow the sport and move the needle across the continent?

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The trade deadline is over and the Raptors can now get on with the business of winning games and positioning themselves for what is looking like a spirited title defence.

For the moment, concerns about Ujiri’s immediate status have passed.

But in the meantime, MLSE will need to figure out what kind of organization they are and what kind of basketball franchise they want to have when the time comes to talk about the future with their most forward-looking employee.

Catch your breath, things are just getting started.

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