This once again feels like the end for Kyle Lowry in Toronto

If it feels like Toronto fans are prepared for every single scenario when it comes to Kyle Lowry’s free agency, it’s because they already went through the entire emotional roller coaster of potentially bidding goodbye to the greatest Raptor of all-time four months ago.

A day before the trade deadline in late March, Lowry got his send-off: one final iconic performance in a win over the Denver Nuggets, a wave to the camera as he walked off the court, and a 20-plus minute post-game presser that felt like a farewell to the local media connecting virtually miles away back in Toronto. —

We already know what happened next. Well, we don’t know exactly what happened on trade deadline day. Lowry was apparently headed to Philadelphia, and then he wasn’t. Miami seemed like a logical destination. But maybe Pat Riley and Masai Ujiiri played a game of chicken and no one dialled the other back at 3 p.m. The Lakers appeared to be a late bidder, but that went nowhere too. Lowry stayed a Raptor, and spent the final weeks of his season mostly playing golf in Tampa and cheering on his teammates from the bench.

Even at age 35, Lowry’s approach to free agency hasn’t changed. At his exit interview after the season, he talked about the importance of money and years, and the ability to continue providing for several generations of his family. Lowry mentioned stability, a positive for anyone hoping for his return to Toronto, but also the desire to win a championship, which could portend a departure from the franchise where he’s spent the past nine seasons.

Philadelphia and Miami remain the most logical destinations for Lowry this summer should he decide to move on, but New Orleans, Chicago and other suitors have emerged. There will be significant demand for Lowry, and why not. For most of the past decade, the Raptors have been able to roll out Lowry with any four players and win 50 games every season. He can vault teams like the Pelicans and Bulls into playoff contention. The Sixers and Heat would further solidify their status as serious contenders with Lowry.

The main question will be what exactly Lowry’s priority is? If it’s to be on a championship timeline right away, Toronto will not be the first choice. Even with an incoming No. 4 pick, the Raptors do not project as serious title contenders next season. If it’s stability and money, Toronto can provide both.

It leads to the next question. Are the Raptors willing to pay whatever it takes to bring Lowry back? They can go over the cap to re-sign him. At the trade deadline, reports suggested Lowry was looking for an extension in the range of around $25 million annually. Given the number of suitors and the lack of other premium options in free agency, and the fact the league just watched two teams who were elevated by the acquisition of new point guards (Jrue Holiday and Chris Paul) in the Finals, you have to imagine that’s the starting bid and not the closing price.

From a sentimental standpoint, it would appear to be a no-brainer for the Raptors to outbid everyone on the market to bring Lowry back. But we know even though Ujiri loves to embrace and push the idea of the Raptors franchise as a family, he has never let those feelings get in the way of business. That’s how DeMar DeRozan left town in exchange for Kawhi Leonard and a legitimate shot at the championship. It’s why Serge Ibaka left for the Clippers.

In the end, it’s always business, never personal. Ujiri professed his desire to chase another championship at his own exit interview after a forgettable season in Tampa Bay, and scoffed at the idea of making a play-in tournament. Ujiri dreams big. He always has. On a team that has seen most of its championship roster turned over since 2019, does paying a 35-year-old point guard a premium price make sense?

In a perfect world, the two sides agree on a price and Lowry returns to Toronto, reunited with the city that has grown to worship him as the most important player in franchise history. Lowry remains on the team for the next three years while Ujiri reshapes the roster and gets the Raptors back into contention.

Or, Lowry decides to take a bigger payday elsewhere when the Raptors draw a line in negotiations, or he simply decides the desire to compete for a championship right away outweighs all of the other factors in consideration. And both sides agree to move on, and perhaps the Raptors recoup a few assets via a sign-and-trade on Lowry’s way out.

Set the sentiments aside, and the latter feels like the more realistic scenario. It doesn’t always have to end with a bitter fallout, a trade request or a failed negotiation. Sometimes, things just have a natural and logical endpoint. That’s what it felt like at the trade deadline in March for Lowry and the Raptors. As the start of free agency approaches, it still feels very much the same.

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