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Josh Lewenberg

TSN Raptors Reporter

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TORONTO – Masai Ujiri has had his hands full recently, so you can understand why his contractual status may not be top of mind.

After advising the NBA on its return-to-play strategy early in the pandemic and spending months with his team in the Orlando bubble, while continuing to embrace a leadership role in the ongoing fight for racial justice and equality, the Toronto Raptors president remained busy navigating the draft and free agency.

At the same time, Ujiri was working closely with the Canadian and American governments in the hopes of securing the necessary clearance for his team to host games north of the border this coming season. Once the bid was denied, he helped oversee their temporary relocation to Tampa.

He and his not-for-profit organization, Giants of Africa, just finished planning their seventh annual event honouring the life and memory of former South African president Nelson Mandela, which was held virtually last week – a cause that is near and dear to Ujiri’s heart.

Meanwhile, his stated goal of securing new contracts for his Raptors staff is nearly completed – starting with the extension for head coach Nick Nurse in September and culminating in general manager Bobby Webster’s deal, which, according to Ujiri, is “pretty much done.”

As the Raptors get set to open training camp this week – their first team practice is scheduled for Sunday – and tip-off the 2020-21 campaign at “home” to New Orleans on December 23, the elephant in the room is Ujiri’s own future with the club.

One of league’s top executives, the 50-year-old Ujiri is going into the final season of his current contract. In September, he told the media that he still hadn’t spoken to ownership regarding an extension, and on a Saturday morning conference call, he gave no indication that anything had changed in that regard.

“There’s just been so much [going on],” he said. “Honestly, it’s not a matter of not doing it, I think there’s just been so much [and] I’ve pushed it [back] until, I think, we get through a lot of this. There’s just so much going on with this relocation, and the focus, I don’t want to be distracted that way.”

With his people taken care of and the team getting comfortable in its new home, the time is approaching for Ujiri to sit down and evaluate his next move.

Already among the association’s highest paid execs, Ujiri should have all the leverage he needs to essentially craft the terms of his new deal. Short of sliding a pen and blank cheque across the table – or however contracts are drawn up in the COVID-19 era – it’s hard to imagine Maple Leafs Sports & Entertainment balking at anything Ujiri could or would ask for, not only because of what he’s accomplished in Toronto or even the number of interested teams that have come calling, but because of how crucially important he is to where the franchise wants to go from here.

Ujiri and the Raptors have made no secret of their ambitions for the summer of 2021. Maintaining cap flexibility, and the option of opening up the requisite space to offer a max contact, has been a top priority – it’s motivated nearly every decision they’ve made, or haven’t made, over the past couple years.

Since taking the job atop Toronto’s front office back in 2013, Ujiri has checked off a lot of boxes on his list of goals. He wanted to build a state-of-the-art practice facility and get the franchise its own G League – at the time, D-League – affiliate. He wanted to change the culture of an organization that had fallen on hard times and was mired in a team record five-year playoff drought. He wanted to build a winning foundation, and yes, he promised to bring the city a championship. He’s delivered on all of those things, and then some.

Just about the only thing he’s yet to accomplish, and another stated goal of his, is to finally lure a star free agent – at or close to the peak of his career – to Toronto. In 25 years, it’s never been done.

For the bulk of their existence, the Raptors have been haunted by the stigma that star players don’t want to be in Canada. That many of their own stars left or engineered their exists, particularly in that first decade – Damon Stoudamire, Tracy McGrady, Vince Carter and Chris Bosh – certainly didn’t help dispel that narrative.

Under Ujiri, these Raptors are looked at very differently – within their own city and country, but also around the league. Keeping their own stars no longer seems like an impossible task – DeMar DeRozan and Kyle Lowry both signed multiple contracts to stay in Toronto and, most recently, Fred VanVleet did the same – and they’re confident that the reputation they’ve built is strong enough to attract the league’s best players on the open market.

It’s been a while since they’ve had the chance to test that theory. Operating as an above cap team for most of Ujiri’s tenure, the Raptors haven’t had significant money to spend in free agency since they signed DeMarre Carroll to an ill fated four-year, $60-million deal in 2015.

They’ve set themselves up to be major players in the highly anticipated 2021 free agency sweepstakes, which could include the reigning two-time MVP – and long-time Ujiri target – Giannis Antetokounmpo, among other stars. The question is, will Ujiri be around to make the sales pitch?

If Ujiri is succession planning, the Raptors would be in capable hands with Webster and assistant GM Dan Tolzman - a couple of rising stars in the executive ranks – steering the ship. Still, there aren’t many people in the business that can replicate Ujiri’s presence and salesmanship. He’s the guy you want leading any meeting with a star free agent, especially if that free agent happens to be a certain Greek forward, with whom Ujiri already has a relationship. But what if Ujiri, himself, is also a free agent?

Simply put, the Raptors can’t let that happen. Assuming there hasn’t been any progress made on the extension front, it’s hard to believe that’s an ownership choice. Meaning, Ujiri will decide if and when the time is right to start the conversation.

Now that the dust is settling on an eventful 2020, this would seem like as good a time as any.

“I don’t know what the timeframe will be,” said Ujiri, who was asked if he anticipates getting a new deal done over the coming months. “I go into this thing with a very positive mind and attitude. And we hope it goes that way.”