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Josh Lewenberg

TSN Raptors Reporter

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TORONTO – Thirty-seven minutes into his virtual end-of-season media availability, it was suggested to Kyle Lowry that he might be approaching the longest player press conference in Raptors history.

“Who has the record?” he asked. “Who has the record? Me?”

Even in an age where the most obscure stats and milestones are tracked by somebody somewhere, this one would be difficult to dig up. But let’s go with it. Why not? Having just completed his ninth season with Toronto, the 35-year-old point guard already owns or has a share of most team honours and accomplishments. What’s one more? And who could have seen this one coming?

Not long ago, getting Lowry to stand in front of a backdrop and talk into a sea of microphones for even 45 seconds was like pulling teeth. On Tuesday, he took questions and held court over Zoom for 45 minutes.

He cracked jokes and challenged reporters to a round of golf. He reflected back on one of the most difficult seasons of his career, spoke highly of his Raptors teammates, shared some insight on his own personal evolution and what continues to drive him after all these years and, yes, he also looked ahead to his uncertain future.

“I'm just gonna go out here and enjoy my summer, train, get my body right, get my mind right, enjoy my family time,” said Lowry, an impending free agent. “With all that being said, I'm kinda BSing around your question because I don't have an answer for you.

“We'll see what happens. Of course, Toronto's always gonna be home to me. It's a situation I would love to be in, and if it works out, it works out. If not, then we make choices on what's best for myself and my family.”

There’s a reasonable chance that we’ve seen Lowry play his last game as a Raptor; there’s also a chance that we haven’t. If you’re trying to read the tea leaves, you can probably talk yourself into either direction.

Lowry wants to compete for more championships. That aligns with Toronto’s philosophy, but his timeline may not match the organization’s. There are teams that can and will offer him a better chance to do that over the next two or three years.

At the same time, and to his admission, money and term remain important. He’s not one to take less than what he believes he’s worth – whether that’s to stay with the Raptors or to go elsewhere.

“I’ll be honest with you guys, I would tell you if I felt old, but I feel great,” Lowry said. “I still amaze myself, like I’m still a young spring chicken. My age may not say that, but I still move and shake like I’m a young spring chicken.”

Even at 35, he’s shown he can impact the game at a high level and he wants his next, and perhaps final, big NBA contract to reflect that. Only three players have ever signed a deal worth at least $20 million for multiple years at age 35 or older: Kobe Bryant, Dirk Nowitzki and LeBron James. Lowry intends to add his name to that prestigious group, but it’s hard to see him getting that kind of money or term without the Raptors, who can offer more than any other team, or without their help in a sign and trade.

He acknowledged that there might be some “unfinished business” for him in Toronto, coming off a year in which the team missed the playoffs and spent the entire campaign playing its home games in Tampa. He also noted that the future of team president Masai Ujiri, whose contract is also set to expire, could also be a factor in his decision.

Where Lowry ends up will depend on how he weighs his priorities, what his market looks like in August and in which direction he and the Raptors decide to go when the time comes.

“I'm older [than when I was a free agent in 2017],” Lowry said. “That's one. [I’m coming] off one of the most difficult years in NBA history, with COVID, the relocation [to Tampa]. And then also this is way different with my family, and my kids being older. My kids, they're at a point where stability is going to be key. They've had some good stability in Toronto so far, and we'll see what happens with that. It's a big difference because of my family situation, where I'm at in my career. I want more championships, that's always been the goal. Yeah, the money comes with that and you'll get paid, but championships are a big key into why I play this game.”

The Raptors also have to decide what’s best for them. Re-signing Lowry would cut into most, if not all of their salary cap space. It’s no secret they’ve prioritized that flexibility; it’s motivated almost everything they’ve done, or haven’t done, over the past few years, from declining to offer Serge Ibaka a second season of guaranteed money last fall to signing players to short-term deals with team options. They’ve had the summer of 2021 circled on their calendar for a while.

But things change, that’s why there’s value in remaining flexible. Their presumed target, Giannis Antetokounmpo, is no longer on the board. Several other stars have also signed contract extensions, including Paul George and Jrue Holiday. Victor Oladipo is hurt. Suddenly, this crop of free agents has thinned out and Lowry projects to be one of the best players available.

They could bring him back, retain Gary Trent Jr. (a restricted free agent) and add a few depth pieces to the young core of Pascal Siakam, Fred VanVleet and OG Anunoby, as well as their lottery pick, which will more than likely fall in the top 10 of July’s NBA draft. But is that team good enough to get them back to where they want to be?

You could make the argument that they’re better off going younger and using that $20 million or so of cap space elsewhere. You could also argue that Lowry deserves to spend his final seasons chasing another ring or two with the Lakers, Clippers, 76ers or the Heat.

Maybe Lowry has in fact played his final game as a member of the team he’ll forever be synonymous with – and if that’s the case, that 37-point masterpiece against the Lakers will go down as one of his best ever. But we’ve been down this road before, most recently when they opted not to move him ahead of the March trade deadline.

“I told Freddy [in] January, I wanna finish the season out, I feel like we can do something special,” Lowry recalls. “I’m a man of my word. I’m not gonna force [a trade]. I trust the decision making of Bobby [Webster] and Masai. They decided not to do it.”

“[Ujiri] was in open communication with me about it. I’m not that guy. I’m gonna go out there. If I said something in January that I truly believed, I stuck with it. Those guys had the final decision, and they made the call not to [trade me]. I roll with what they’ve done the last eight years. I haven’t been happy about all the things they’ve done, but I rolled with it and figured it out.”

Over the years, something has always kept Lowry and the Raptors together, even in moments when a split seemed inevitable. Maybe it’ll happen again. There’s too much history and too much mutual respect between them to rule it out.

Even as they transition to a new era, the Raptors aren’t going to find a better leader and mentor for their young players. They’re not going to find a player who better represents their culture and what they stand for as a franchise. Even as he tries to figure out what he wants out of his last few seasons, Lowry isn’t going to find an organization, a city, country or fan base that appreciates him more.

Perhaps that’s what extends their already iconic relationship, but none of those things are going to change – even if the logo on the front of Lowry’s jersey does.​