Facing familiar story after playoff elimination, Raptors may be best turning to a familiar face: Kawhi Leonard

Eight years ago, Toronto traded for Leonard to break out of a rut and ended up winning the title -- could it work again?

Sam Quinn

May 3, 2026

11:01 pm ET

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7 min read

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Stop me if this sounds familiar, Raptors fans. You've just overachieved in the regular season. You're facing the Cleveland Cavaliers in the playoffs. Your best overall player has largely held his own, but your designated star scorer just couldn't replicate his regular-season success. Your young players flash upside that you think might materialize into greatness on the right roster. A promising season ends because you ran into an opponent with more star power.

Cheer up. At least it wasn't LeBron James this time. The pieces otherwise fit cleanly. The Raptors built an identity around defense, transition and depth this season that launched them into a surprise playoff berth. Scottie Barnes acquitted himself very well in his first postseason since his rookie year, much as Kyle Lowry typically held up his end of the bargain in those LeBronto losses. What's more, Toronto's injuries may have inadvertently shown the Raptors what the best version of their team should ultimately be. With starting point guard Immanuel Quickley out, Barnes functioned as the point guard in this series, taking advantage of his playmaking while minimizing his shooting woes. He just needed more scoring help.

But playing the role of DeMar DeRozan this time around was Brandon Ingram, a surprise All-Star choice this season who struggled mightily against Cleveland before getting knocked out with a heel injury. RJ Barrett held up his end of the bargain in a supporting role but just can't be expected to match baskets with the NBA's best scorers. Collin Murray-Boyles was one of the breakout players of the first round, but Jamal Shead and Ja'Kobe Walter were also defensive menaces. Squint hard enough and you'll see shades of Fred VanVleet, OG Anunoby and Pascal Siakam. They just need to be put in the right situation.

The Raptors took two notable steps to address their last handful of playoff losses to Cleveland. The first was a coaching change. Don't count on another. Darko Rajaković impressed in both the regular season and playoffs. He proved strategically adaptable against Cleveland and installed a motion offense that made the most of Toronto's limited shooting. He shouldn't go anywhere.

The second move? That one's a bit more repeatable. They traded for Kawhi Leonard.

We all remember how it went last time. Toronto, stuck in a regular-season rut with a LeBron-shaped playoff ceiling, broke up its Lowry-DeRozan pair to add Leonard on an expiring contract. James moved West, but Leonard proved productive enough to carry Toronto through a newly deep Eastern Conference and ultimately past LeBron's frequent Finals foe, the Warriors, to give the Raptors their first championship.

Leonard left soon after to sign with the Clippers, who are now under investigation for circumventing the salary cap to overpay him. Whether that investigation forces Leonard out of Los Angeles or not, the Clippers are already moving in another direction. They traded James Harden for Darius Garland at the deadline, then swapped Ivica Zubac for Bennedict Mathurin and picks. They're getting younger, preparing for whatever the next iteration of their team looks like. Leonard, who will turn 35 this offseason, no longer fits that vision.

Why trading for Kawhi Leonard makes sense despite the risks

Trading for Leonard this time around would probably be a bit more costly, at least in terms of picks. Ingram likely doesn't hold the trade value DeRozan did at the time, when the Spurs were just trying to remain competitive. The Clippers tend to prioritize championship equity, and a floor-raiser like Ingram is better-suited to a team like this year's Raptors, who are just trying to get in the dance. They'll want picks and they'll probably want Toronto's young big, much like San Antonio did. Jakob Poeltl was a worthwhile sacrifice for Leonard in 2018. Murray-Boyles is not. He will surely be untouchable in any Toronto offseason dealings unless perhaps they take a run at Giannis Antetokounmpo.

Hence, more picks. The Raptors have picks to spend. They control all of their own moving forward and, given Leonard's age, their picks deep into the future would probably appeal to the Clippers. Pinning down his exact value is tricky. He's coming off one of his best and healthiest seasons, but at his age, he's a risk moving forward. Regardless, there will be a market for him. Too many teams need wing defense and high-level playoff shotmaking. He's not netting the massive, four- or five-pick hauls that younger wings have been getting in recent years. It's probably taking multiple picks, though.

The Raptors will explore alternatives. They were linked to just about everyone at the deadline