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Josh Lewenberg

TSN Raptors Reporter

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TORONTO – Raptors fans know what it’s like to spend an entire season reading tea leaves, and it’s probably not an experience anybody wishes to relive.

For months, we all surveyed Kawhi Leonard’s every move. We analyzed his facial expressions and broke down each sentence word for word. It’s not like he gave us much to work with, after all.

What did he mean when he referenced the Raptors as “we”? How much does he seem to dislike the cold weather? He owns a Canada Goose parka – that’s got to be a good sign, right? Wait, was that a smile? Did he smile?

It was an exhausting exercise and one that yielded little in the way of actual results. Despite leading the Raptors to their first NBA title, Leonard left for his hometown of Los Angeles in the summer of 2019, and while many saw it coming, it wasn’t because of anything he did or said during his short time in Toronto.

Still, until the words came out of his mouth, until his decision to join the Clippers became official that morning in July, nobody would have blamed you for speculating. Everybody was doing it to some degree, even Masai Ujiri and the Raptors. Leonard was that important to the franchise. He was worth the anxiety.

Now, Ujiri could be headed into his contract season and a familiar nervousness is starting to creep in. The team president – who’s widely regarded as one of the premier executives in all of professional sports – is currently signed through 2020-21, and has yet to engage in discussion with ownership regarding a potential extension.

“Coming out of this, things are a little raw,” the 50-year-old Ujiri said in a news conference on Thursday. “I'm going to reflect a little bit and we will address it when it's time to address it. It's not something I'm going to do in the media and publicly, with respect, but no I haven't had conversations.”

“It's been an obligation for me to take care of my leadership team, obviously starting with [head coach] Nick Nurse. Super excited about that, and him. The future is bright. But in terms of me, I haven't had those conversations and I'll wait until those happen in the future.”

The clock is ticking. The Raptors signed Nurse to what’s believed to be a lucrative multi-year contract extension earlier this week. They’re also “close” to inking general manager Bobby Webster – who also has one year left on his current deal – to an extension, according to Ujiri.

There are still a few other members of Ujiri’s leadership team that will need to be taken care of, and some big decisions that will need to be made in free agency. The cloud hanging over it all is the uncertain future of the man making those decisions, though Ujiri doesn’t believe his contractual status will be a distraction heading into a crucial off-season for the organization.

“These things they come and go, they happen,” Ujiri said. “To me, there are no distractions with me, with my team, with the organization. I’m totally fine with it. I understand it gets talked about but there is a focus [and] when there is a time to have a conversation, we will have that conversation.”

If and when he’s ready to have that conversation, you would imagine Maple Leaf Sports and Entertainment will be all ears. Whatever it is that Ujiri wants – whether it’s to get his top lieutenants paid, or to maximize his leverage going into negotiations – he knows he’s in a great spot. Not only did he help take the franchise to new heights, he might hold the key to reaching the apex again.

These next few months will be critical in setting the Raptors up for the much-anticipated summer of 2021 – an off-season that Ujiri has spent years preparing for.

Can the Raptors retain free agent guard Fred VanVleet, who’s coming off a breakout campaign and is sure to command interest around the league, without eating into their coveted 2021 cap space? Can they sell either of their big men – Serge Ibaka or Marc Gasol, who are also unrestricted – on the idea of returning for one year?

It will be a balancing act for Ujiri, Webster and Co. – maximizing the present without jeopardizing the future. That’s one of Ujiri’s many strengths as an executive – he’s been walking that line for years.

“You know how we've dealt with this with our team, we have to really look at what is now, we have to look at the short-term future and we have to look at the long-term future, and after that, we have to look at a key year which is 2021 and free agency,” Ujiri said.

“That’s what our jobs are. We have to face them square on and we will deal with them as they come, as we have in the past. We do respect who are players are and, yes, they are a priority. Fred is a priority for us, our bigs are a priority, Serge is a priority. We have to really attack this head on and we know where their game is, we know how much they can improve, or we try to project that as much as we can.”

Ujiri has accomplished a lot in his seven seasons at the helm of the Raptors’ front office, but the one thing he still hasn’t done is recruit a big-name free agent to Toronto – a stated goal of his since he took the job back in 2013.

He’s built a stable organizational foundation and the type of winning culture that may end up appealing to a superstar player on the open market. He’s worked to free up and maintain cap flexibility for next summer.

Giannis Antetokounmpo – somebody Ujiri has a relationship with and has been pining over since before he was drafted – could be among the players available in a loaded 2021 free agent crop.

Ujiri’s put the Raptors in a position to try and finally land that big fish, the question is whether he’ll be around to make the pitch.

He has never hit a season-saving, series-winning buzzer beater. He hasn’t led the club in scoring or made an All-Defensive Team. He doesn’t have a Finals MVP award, let alone two. However, Ujiri is every bit as important as Leonard was, probably more so when you consider what he’s meant and continues to mean to the Raptors organization, the city of Toronto, and the country of Canada.

He’s the architect that turned the fortunes of a blundering franchise – albeit inadvertently at first – and built them into champions. His Rolodex and unique ability to connect with just about anybody on the planet create endless opportunities. His passion has empowered a fan base and a growing basketball market North of the Border, his charitable work with Giants of Africa – which is near and dear to his heart – has helped lift a continent, and his leadership in the fight for social and racial justice has inspired many around the world.

Ujiri spoke for nearly an hour on Thursday. He praised his Raptors team for their remarkable season and, even in defeat, he commended their efforts inside the bubble – both on and off the court. He said he was proud of them, and the rest of the league’s players, for taking a stand and protesting games in the hopes of affecting meaningful change.

He shared his personal struggle of being away from his family over these past few months, particularly when the security footage was released and brought back some of the emotions he felt after an altercation with the Alameda County sheriff’s deputy in Oakland last year, and after being falsely accused of initiating the encounter.

In terms of his future with the Raptors, he said very little that would indicate what his plans are following this coming season. Although Ujiri is certainly chattier than Leonard, reading the tea leaves won’t be much easier this time around.

Signing Nurse and, likely, Webster to extensions before considering his own – some might see that as a noble gesture from a great leader, a sign that he’s staying and wants a strong team that he trusts around him, others might see it as a succession plan, an effort to take care of his people before moving on.

Combing through a 55-minute news conference and looking for hints or clues is likely a fruitless endeavour, but until Ujiri signs on the dotted line and Raptors fans can start to look ahead to a long-term future that includes the valuable exec, you can understand why some might feel uneasy.​