Knicks report a sign Ujiri’s time with Raptors could be winding down

With rumours swirling (yet again) that the New York Knicks are interested in hiring Raptors President Masai Ujiri, NBA Insider Michael Grange joined Faizal Khamisa to discuss if there's a real possibility that could happen.

Another day, another shot from New York across the bow of the good ship Raptor.

But there’s a twist this time: Unlike past incarnations of what is now a four-year long conveyor belt of rumours connecting Toronto Raptors president Masai Ujiri to a mythical role with the New York Knicks, this time there’s actually a job opening.

The Knicks – winners of a single playoff round in the past 19 seasons and poised to extend their streak of lottery finishes to seven straight this year – fired their team president, Steve Mills, two days before the NBA trade deadline.

Did we mention that James Dolan’s tenure as Knicks owner almost perfectly overlaps with the past two decades of dysfunction during which the league’s wealthiest franchise has floundered almost without pause?

Or that when they didn’t flounder – notably a 54-win season in 2012-13 and that lone playoff series win – Dolan fired the general manager, current Canada Basketball chief executive officer Glen Grunwald?

Mills, the longtime lackey of Dolan, got the boot Tuesday morning after having traded Kristaps Porzingis for pennies on the dollar and cap room a year ago, and failing to use that cap room to sign – or even meet with – any significant free agents this past summer, then firing his head coach David Fizdale earlier this season when it became clear the dog’s breakfast of a roster couldn’t compete. Again.

It was noon on Tuesday when well-connected ESPN NBA insider Adrian Wojnarowski tweeted that Dolan was targeting Ujiri to “ultimately oversee New York’s operations.”

This is – of itself – not news. Similar reports were circulating before the Raptors’ NBA title defence began in October, and more earnestly back in December after Fizdale was fired.

On Tuesday night, longtime NBA insider Marc Stein reported that Ujiri might even bring along Raptors general manager Bobby Webster, whose contract matches the term of Ujiri’s and whose wife – while we’re connecting dots – is from a prominent family in the New York area.

A couple of key nuggets bubbled to the surface back in December, too.

I reported that Maple Leaf Sports and Entertainment — the conglomerate that owns the Raptors along with the Toronto Maple Leafs, TFC and other holdings — had never offered Ujiri an extension (later confirmed by MLSE minority owner Larry Tanenbaum to Sun Media) and that he was all but certain not to accept one if it were offered before 2021 when his contract is up. The expectation was that Ujiri — who had started off as an unpaid international scout barely 20 years ago — was going test free agency.

Another key detail?

That Ujiri may have an out on the five-year deal he signed in the summer of 2016 — which back then was in part a preemptive strike against the Knicks nosing around — that could allow him to hit the market this coming summer. Whether it’s a formal out or more of a gentleman’s agreement isn’t exactly clear.

But it’s not good business for an NBA team to have an executive of Ujiri’s stature going into the final year of his deal without some assurance about the future beyond that. Forcing him to stay the length of the deal if he’s determined to leave seems pointless.

One way or another, the expectation is Ujiri’s status will be cleared up well before the 2020-21 season.

As one league source put it to me recently: “If something is going to happen with Masai and the Knicks it will happen quick, probably a few days after (this) season is over.”

Taken together, a picture seems clear.

The Raptors haven’t offered Ujiri an extension, he’s determined to become a free agent and he may have an out on his deal this coming summer.

Short answer? Ujiri is gone.

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But here are some caveats: A person with deep NBA ties, and who is familiar with Dolan, said that betting on the Knicks owner to have the vision to see a scheme like this through is never wise.

“James is James. 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.”

Translation: Even if Ujiri was being set up for him on a tee, Dolan might go a different direction. He’s that unpredictable.

The source seemed to think that Dolan may have already gotten over his apparent infatuation with Ujiri and has become intrigued by another path — which fits with subsequent reports that the Knicks will be interviewing a prominent player agent for the job, copying a model that has worked successfully in Golden State and with the Lakers.

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Another key point? Raptors minority owner Larry Tanenbaum is chairman of the NBA’s board of governors, and who in that group likes the idea of rogue owners poaching valued executives still under contract?

“There are eyes all over this for tampering,” said my source.

But those caveats aside, it’s not hard to see a scenario where Ujiri’s term running the Raptors is winding down with the tick-tocks getting ever louder.

Would Ujiri subject himself to working under Dolan, who is loathed in his own market and has a two-decade track record of rash hires and even more rash firings?

Those close to Ujiri say that there’s no chance he’d be intimidated by the challenge, given the size of the opportunity.

Turning around the Knicks and winning the first NBA title there since 1973 would make Ujiri the modern-day Jerry West. He’d be the toast of a league that’s desperate for teams to be relevant in the biggest TV markets as viewership numbers slide.

The fact that he’d be able to do it as the highest-paid executive in sports would be nice, and that he’d be able to accelerate the momentum behind his Giants of Africa foundation by leveraging the Knicks and New York might be the ultimate carrot.

At the very least, Ujiri has created what any shrewd executive craves in their bones: multiple points of leverage.

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There’s the matter of compensation — presuming Ujiri doesn’t have a clean out this summer. It’s hard to imagine a scenario where the Raptors allow Ujiri to bolt to a team in their own division before the natural end of his deal without being significantly rewarded. How many draft picks that might be is a great question, as would how much deeper a hole that would put the Knicks in?

The possible threat to the stability of the Raptors extends beyond Ujiri and Webster. The entire front office staff, along with highly respected director of sports science Alex McKechnie and head coach Nick Nurse, are on deals that are up in 2021 as well.

Clearly Ujiri’s future with the Raptors hasn’t been felt on the court, where his club has won 11 straight and have the third-best record in the NBA.

But with three starters heading into free agency and franchise player Kyle Lowry going into the walk year of his contract, Ujiri’s status is understandably front and centre.

It’s a question that will linger until Ujiri puts a stop to it by signing an extension or the Knicks go ahead and appoint another team president.

So far, Ujiri has remained silent, and his presence around the team he put together so well has been — observationally at least — much more limited than in past years.

It could be he’s doing what confident executives do — allowing his hand-picked leadership team to take on bigger roles and grow into them.

Or it could be he’s beginning a transition of sorts. This shot might not be across the bow, but right to the heart of the Raptors ship.

We should find out soon enough.

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