Three Directions: Assessing Kyle Lowry’s future with the Toronto Raptors

Photo credit: Douglas P. DeFelice, Getty Images (2021)

If there were one word to describe Kyle Lowry’s impending free agency, that word would be uncertain.

The Toronto Raptors are 27-41 on the season, on the brink of elimination from playoff contention, and their most beloved player is set to become an unrestricted free agent at the end of the season. The Raptors have battled a myriad of obstacles this season and ultimately weren’t able to overcome the odds. The trade deadline in particular was a large point of contention, with several pundits around the league convinced Lowry would be dealt.

To everyone’s surprise, the Raptors opted to keep the franchise icon at the deadline, which at the time was taken as a sign the team would give it one last go with Lowry at the helm.

However, since the trade deadline, Lowry has only suited up for nine of the team’s 24 games. Of those 15 games missed, nine injury reports listed Lowry as out due to rest or injury management. The team has definitively fallen out of the playoff race, and in what could be his final week with the franchise, it is uncertain if Lowry will even play.

If he were to miss the remainder of the year, it would mean his last game of the season, and possibly his Raptors tenure, was one of his finest: a 37-point, 11-assist outing in a resounding victory over the Los Angeles Lakers.

So, where do the Raptors – and Lowry – go from here? The 35-year-old has a hefty salary cap hold of 43.75 million dollars, which essentially restricts the Raptors from making any official signings until that gets resolved.

There are three possible directions the Raptors and Lowry can take this summer, with each of them bringing implications of what the past two months have meant, and what it could mean going forward:

Of course, the first and most obvious option would be for Lowry to return to the team on a contract that benefits both the team and Kyle himself. The Raptors need his leadership in the organization, he is an icon in the city of Toronto, and for both sides to keep going makes sense for a lot of reasons, making this the likeliest option of the three.

If Lowry were to return, he would become the first Raptor ever to have played for the team ten seasons or longer, surpassing DeMar DeRozan’s nine-year career with the team. For the team to continue this partnership would be significant, and it would solidify Lowry’s Raptor lore even further as he would overtake DeRozan’s records for games played and minutes played. For the greatest Raptor of All-Time, this would mean something to both Lowry and the city.

As the owners of his bird rights, the Raptors can offer Lowry the most money. Given that they would want to resolve this quickly to eliminate his large cap hold, they should work quickly to get this deal done and retain a valuable asset in Lowry.

On the 45 million dollars, the team could front-load this contract in order to preserve cap flexibility for next summer and give Lowry more money now, finessing a split of 25/20 or even steeper at 28/17. The Raptors project to have their flexibility more so from the low cap hold on Gary Trent Jr. and by using the non-guaranteed contracts to absorb a player from another team, so there are plenty of options with Lowry too.

What It Means

The Raptors’ plan to rest Lowry would then indicate that they’re preserving him for when the team hopefully returns to Canada for the 2021-22 season with a healthy and revamped roster, ready to compete once again.

The team figures to be one of the more aggressive this summer in pursuing improvements to the roster, with a high draft pick and several trades to make. Outside of the core pieces, there will likely be wholesale changes to the depth beside Malachi Flynn and Chris Boucher.

The fact that he rested in the team’s most implicit game of the season on Thursday should have been telling this is the case.

Ultimately, there is still more in this partnership for both Kyle Lowry and the Raptors. It also stands to reason that they will more than likely continue down this road together. For the city to have somebody to call Mr. Raptor for the next decade would mean a lot to the next generation of Canadian basketball fans. Barring any massive changes, there is no reason this shouldn’t stay the same for years to come.

Two teams that were rumoured to be in hot pursuit of Kyle Lowry at the trade deadline, they could once again make a run at the guard this summer.

Lowry isn’t getting any younger and he wants to compete. In the event that he is serious about vying for a championship, a possible scenario is moving in a sign-and-trade to a team that should be closer to contention immediately, such as the Miami Heat or Philadelphia 76ers.

Miami has only five players with guaranteed money for next season, and the remaining ten either have team options or are set to become unrestricted free agents. While they project to have a max free agency slot available, it would require renouncing the cap holds and declining team options on every single player, meaning they’d be compromising their entire depth to sign Lowry. Thus, a sign-and-trade would be ideal in which they’d pick up a team option and flip the player in a three-team trade, with draft compensation coming back to the Raptors.

With this, the Heat could field a dangerous starting five of Kyle Lowry, Tyler Herro, Victor Oladipo, Jimmy Butler, and Bam Adebayo. The Heat were strong in their courtship for Lowry at the deadline due to his championship intangibles and strong relationship with Butler. This summer could be an opportunity to bring all of them together, and Pat Riley has always been a bold executive.

Conversely for Philadelphia, they are capped out, and the only feasible sign-and-trade would be to attach draft picks or Matisse Thybulle to George Hill and Seth Curry. Hill’s contract is only partially guaranteed for 1.3 million dollars next season and the Raptors could pick up a quality depth piece in Curry, plus whatever draft compensation they yield. The Sixers, meanwhile, would get a serious upgrade at the guard spot and find an excellent fit next to Ben Simmons as an off-ball, do-it-all guard.

What It Means

If Lowry asks to move to a contender, it would certainly be understandable from his position and it simply means that he wants the best chance to win another championship.

As for the end of this season, Lowry leaving in a sign-and-trade would indicate the team was indeed intent on making one final run with Kyle at the helm, and when it became apparent that it wouldn’t happen, he rested more to avoid injury for his next contract and remain fresh for the upcoming season.

Although the Raptors will undoubtedly yield a lesser return than they would have had they moved Lowry at the deadline, but they will still be able to salvage some type of asset return on a deal. For many reasons, the team’s success never came this season, but the start of next season would be a true passing of the torch to the new era of Raptors.

It’s tough to imagine a world where the team doesn’t have Lowry or DeRozan, but the good news is the team should be improved next season regardless with improved depth, health, and not playing 72 road games.

While this would be the worst possible outcome, it also stands as the least likely by an extremely wide margin.

While the chances are slim, as it would require an immense sacrifice on both ends, Kyle Lowry is still a free agent and will have the right to sign with any team of his choosing, should they have the means to do so.

Contending teams will not have more than the mid-level exception to offer due to being capped out, and Lowry would be giving up a significant chunk of change to do that. Not only this, but after balking on trade offers at the deadline, the Raptors would be losing Lowry for nothing.

Neither side would be willing to sacrifice so much just to end a nine-year partnership this way. And nor should they, it would be disingenuous to Lowry, everything he’s accomplished for the franchise, and equally non-beneficial to the team in terms of maximizing assets. Both sides owe it to each other to find a way to continue down the path together, or to find Lowry the right situation where he gets paid, accomplishes his goals and the Raptors recoup assets.

What It Means

To decide to not pull the trigger at the trade deadline only to have Lowry rest the majority of the second half and then leave without getting any compensation at all would be… puzzling, at best. Something would need to have gone catastrophically wrong for that to happen, as the Raptors don’t want to lose their most beloved player for nothing.

It would also mean Lowry would be taking significantly less money on the market, which goes against everything he believes about the NBA being a business and players needing to do what is best for them. Given that there is absolutely zero benefit to either side, the Raptors and Lowry would never approach this unless things soured badly for whatever reason (they won’t).

Regardless of the outcome, Kyle Lowry’s career with the Raptors is immortalized as the heart and soul of the team who gave Canada its first NBA championship. There is zero doubt that the number seven — HIS number — will never be worn by a Toronto Raptor again after he is gone.

If these truly are Lowry’s final days in a Raptor uniform, it is important for fans to cherish his time before it disappears, and ensure his legacy is remembered in only the best of lights.

By the same token, should Lowry stick around to become the longest-tenured Raptor ever, fans shouldn’t take that for granted and give him his flowers while he’s still in front of them. Lowry has given the Raptors everything throughout his time here, and the organization will remember what he did for a long time to come.

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