Amid rumours, have Raptors missed chance to keep Ujiri from free agency?

NBA Insider Frank Isola joined Tim and Sid to discuss what the New York Knicks would need to do if they were going to make a push for Toronto Raptors' president Masai Ujiri.

They will keep coming.

Every time an NBA franchise goes through a wave of dysfunction and is seen casting about for a saviour, Toronto Raptors president Masai Ujiri’s name will surface.

Since the New York Knicks seem to be setting new standards for dysfunction, Ujiri’s name gets attached to the sagging flagship franchise all the time, seemingly.

The latest came when the Knicks fired coach David Fizdale Friday and well-connected NBA media voices immediately – and not for the first time — suggested that management changes are bound to follow and Knicks owner James Dolan has his heart set on prying Ujiri away from the Raptors.

Get in line. The Washington Wizards came after Ujiri hard last spring. The Los Angeles Lakers made some backchannel inquiries as they tried to gain traction in the early stages of the LeBron James era.

There will be others between now and the summer of 2021, when Ujiri’s contract is set to expire and he will arguably become the NBA’s hottest free agent not named Giannis Antetokounmpo.

The Raptors’ ownership, Maple Leaf Sports and Entertainment, could have avoided some of this noise by simply giving Ujiri an extension and a blank cheque this past summer but – contrary to a report that Ujiri turned down an extension – there has never been one been offered, according to sources.

Which is understandable in some ways. It’s not like Ujiri’s current deal didn’t have lucrative bonuses tied to winning a title. And in most businesses – even with NBA stars – discussion doesn’t typically begin for extensions until a year before a current deal expires.

From MLSE’s point of view, having to talk contract with their well-compensated executive every time a trainwreck of a franchise has a tantrum elsewhere is hardly a way to run a business.

The downside is that even with Ujiri under contract through 2021, the door is open for speculation about what happens next – no differently than a slow news day around the league can be filled projecting where Anthony Davis and James were going to end up in years past or Antetokounmpo will in years to come.

Could Ujiri not being locked up even plant the smallest seed of doubt in his mind about how he’s valued?

Who knows, but as Ujiri’s end date grows closer the drumbeat about his future will likely only get louder.

It comes with the territory when your career winning percentage as a general manager or president in your 10th year with two franchises is .651 – a 53-win pace – and your teams have made the playoffs every year on your watch.

Or that you assembled a team that won the 2019 NBA title without a single lottery pick on the roster – an NBA first.

Or that with 11 picks over 10 drafts — and only one selection higher than 20th — you have overseen the selection of nine NBA rotation players; including Pascal Siakam, a budding superstar taken 27th in 2016.

Or that your undrafted free agent signings – Fred VanVleet and now Terence Davis — perform like lottery picks.

Or that you have a habit of making bold, high-impact trades, smart coaching decisions and sensible contract signings.

Or that you have an off-court persona that somehow perfectly balances a confidence bordering on arrogance – the kind needed to have a franchise and even a city change how they see themselves — with a genuine people-first humility.

Or that your greatest passion is a charitable foundation – Giants of Africa – that is contributing to basketball as an agent of change on the continent and African basketball as an agent of change within the NBA.

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The question is what MLSE should do to keep the wolves – or in particular, the Knicks – at bay.

The answer is everything, but that may not be enough. And it may even be too late.

The last time the Knicks were in the market for an executive named Masai was in the summer of 2017 when Dolan realized the unprecedented five-year, $60-million deal they lavished on Phil Jackson – a Hall-of-Fame coach with zero front-office experience – was a bad investment.

The threat was real, but MLSE was in a strong position at the time.

After the Raptors made the Eastern Conference Finals in 2016 – at the time a franchise high point – Ujiri’s existing deal was torn up with two years remaining. Instead, he was rewarded with his current five-year contract through 2021, elevated to president and placed among the upper tier of NBA executive salaries.

Ujiri’s hand-picked executive team and scouting staff were rewarded with new deals, titles and raises as well.

It was recognition for a job well done and also defence against a potential raid from the Knicks, whose interest began floating around NBA circles during the 2015-16 season.

So, when the corporate headhunters and backchannel whispers eventually came, MLSE called the Knicks’ bluff and demanded multiple draft picks as compensation, confident of Ujiri’s loyalty.

The Knicks got the message and slinked off.

In the meantime, the Knicks’ situation has gotten more desperate and Ujiri’s star has only risen higher.

The real question is not whether Ujiri was offered an extension or not, but why would he sign one?

Why would he not explore free agency?

It would not be about creating leverage or posturing to squeeze an extra few dollars. All the leverage Ujiri needs is on his resume at this point.

He would simply be an ambitious professional at the peak of his career, pausing to consider all of his options. Not doing so is the more unlikely scenario.

And betting that Ujiri would shy away from the chaos the Knicks currently represent would be folly.

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In my opinion, there is every reason for MLSE and the Raptors to consider the Knicks a very real threat to hire away Ujiri when the time comes.

Some of the reasons are obvious:

• It’s hard to imagine the Knicks would lose a bidding war, if it came to that. Ujiri would be positioned to be the wealthiest executive in all of professional sports. Certainly MLSE is a well-heeled ownership group, but their majority owners are a pair of publicly traded companies; there may be limits. The Knicks? Restraint isn’t their thing.

Even with nearly 20 consecutive years of dazzling dysfunction, the Knicks are the NBA’s most valuable franchise at $4 billion, according to the most recent calculations by Forbes. The Knicks’ issue has never been money, but rather what they have spent it on.

• The notion that Ujiri would somehow be unwise or even scared to go to work for the combustible Dolan doesn’t hold water, even if a lot of highly regarded basketball people have had their career low points working for him.

Ujiri spends his spare time going to war-torn regions in Africa in the name of basketball. He broke into the league by working for free, spending his savings to travel the world and prove his worth as a basketball talent evaluator. His first task as a rookie general manager was to trade then-Denver Nuggets superstar Carmelo Anthony. With the Raptors at a precipice, he went all-in on Kawhi Leonard while the rest of the NBA fiddled. In short: he’s not going to be frightened about the challenges presented by working at Madison Square Garden.

For good reason there is nothing in basketball that would frighten him, both because of how he got this far and because he’s worldly enough to know what being scared really is. The challenge would intrigue him, the downside risk wouldn’t deter him.

• There is probably no city in the world that would provide a greater opportunity for Ujiri to further the ambitions of his foundation than New York, where he could walk to the United Nations for lunch and meet potential billionaire donors for breakfast. It’s a global nerve centre for business and politics and it would be impossible for Ujiri to fail to expand his already considerable network there.

If his ultimate goal is to further his causes in Africa, New York is a better base to work from.

The question, really, is if there is anything MLSE can do to make Ujiri a semi-permanent piece of the Toronto landscape, to make the Knicks or other threats distant or far-fetched?

On that front, their best chance to put the coming drama to bed may have passed.


In the Raptors’ champagne-soaked locker room after the Game 6 win over Golden State to clinch the NBA title, MLSE part-owner and longtime chairman Larry Tanenbaum was asked about reports that had come out that night of the Wizards’ mega offer for Ujiri.

“I know Masai. He’s like my son,” Tanenbaum said at the time. “There’s no chance he’s leaving Toronto … I think if you ask Masai, he’s got everything he wants.”

And sure enough, Ujiri made clear his commitment to the franchise and the city in his post-championship press conference. It was sincere, as his actions the past six years and counting demonstrate.

But perhaps that post-champagne glow might have offered an opportunity to talk about Ujiri’s long-term future.

Regardless, Ujiri’s tenure has been without question the most successful in Raptors history and the most riveting of any major Toronto sports franchise in more than a quarter-century.

It’s still going strong and may yet run well into the future.

But the opportunities are going to keep coming, and nothing this good lasts forever.

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