How Will the Raptors Pivot Following Kawhi Leonard’s Departure?

Now that Kawhi Leonard has signed with the Clippers, what's next for the reigning champion Raptors? Is an all-out rebuild coming in the near future? Or should they keep their roster intact and remain competitive in a weaker Eastern Conference?
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Not even a championship could keep Kawhi Leonard north of the border. The two-time Finals MVP left Toronto for Los Angeles on July 6, marking an unprecedented move in free agency history. Never before had a superstar left his team directly after winning the Finals outside of retirement. But as we’ve been reminded since his Spurs holdout, Kawhi is just a different dude. 

We’ve discussed Leonard’s fit with the Clippers at length, detailing the potential dominance of the Leonard-Paul George pairing. But where does Kawhi’s blockbuster decision leave the Raptors? Even as Toronto fans bask in the glow of the 2019 Finals, an uphill climb awaits. Can the Raptors compete for a second straight run to the Finals, or is a teardown imminent? Toronto’s complicated future lies somewhere in the middle.

We should hold on the calls for a Toronto teardown in 2019-20. The Raptors still boast a deep core in a weakened East, situated in a similar spot to Boston entering next season. Neither team is a legitimate title contender, but a friendly bracket could land them in the conference finals. Perhaps another deadline deal like February’s Marc Gasol trade can lift Toronto’s ceiling back into the Finals discussion. The current roster sans Leonard is headlined by Pascal Siakam, Kyle Lowry, Serge Ibaka and Gasol, a strong, cohesive core even given the latter trio’s age limitations. 

Toronto would be smart to ride its wave of Finals goodwill through one more year, slated to reach the Eastern Conference playoffs in 2020 for the seventh consecutive season. Such a decision comes as much from practicality as sentimentality. Lowry, Ibaka and Gasol all have limited value even as expiring contracts in 2019-20. Lowry could fetch a late first, but Gasol and Ibaka are likely in pair-of-seconds territory. Dealing the trio of veterans won’t swing the franchise’s future in the 2020s. Stripping the roster for parts is presently unnecessary just one season after winning the Larry O’Brien Trophy. The harder decision will arrive in July 2020.

Gasol and Ibaka won’t land sizable contracts in free agency, and a return to Toronto doesn’t vault the Raptors back into the conversation for the East crown. The Raptors will be just fine letting the frontcourt veterans find a new contender. Their major question in the backcourt will have a much more complicated answer. 

Leonard is clearly the most talented player to ever don a Raptors uniform, but Lowry is in the conversation of Greatest Raptor Ever. Toronto reached the postseason just five times before Lowry’s arrival in 2012. The franchise has now appeared in the playoffs in six straight seasons, adding the 2019 championship to boot. Lowry ranks fourth on the franchise all-time points list and second in assists. Saying sayonara to a future jersey retiree is never easy. 

Would keeping Lowry be prudent as Toronto transitions into its post-Leonard era? A short-term contract could be worthwhile from the Raptors, but anything approaching Lowry’s previous three-year, $100 million deal is a complete non-starter. Lowry will be 34 by the 2020 postseason. Small point guards don’t necessarily age well, and Lowry is two seasons past his peak. Finals hero Fred VanVleet should be ready to take over the starting role sooner than later, and he’s also in line for a new contract in July 2020. Shelling out big bucks for a pair of undersized point guards feels foolish. VanVleet’s upside could leave Lowry searching for a payday elsewhere in a weakened free-agent class. 

Lowry’s free agency will be a fork in the road for Toronto. The Raptors could string out their core through the next few seasons and attempt to keep its playoff streak alive. But an underwhelming half-measure doesn’t appear to be in Masai Ujiri’s DNA. Toronto’s president was ready to tear down the team’s core before the Leonard deal emerged, tired of falling short with Lowry and DeMar DeRozan each spring. Trading for Leonard became Ujiri’s Get Out of Jail Free card. Keep Leonard after 2018-19 and a contender would be in place for the next half-decade. Lose him in free agency and a rebuild can begin in earnest. Ujiri should seize the opportunity once Lowry’s contract expires. 

Raptors fans will likely bask in the glow of the 2018-19 season, blissfully watching Leonard’s postseason heroics on a loop as Toronto’s veteran core makes another playoff push. But delaying the inevitable is a recipe for disaster, and next summer should provide the clear pivot point for Ujiri and Co. Toronto has an enticing young core with Siakam, VanVleet and OG Anunoby. The trio should increase its role in 2019-20 with Leonard in Los Angeles, and the organization will be fully theirs by July 2020. This season can provide a satisfying gap year before the start of a new era. A rebuild should begin in earnest by next offseason.