Why the Cavs Path to Contending Just Got Tougher with Kawhi Leonard in Toronto

After a hard-fought first round with Cleveland last year, the Raptors have officially re-acquired one of their all-time greats.

Mar 11, 2019; Cleveland, OH, USA; Toronto Raptors forward Kawhi Leonard (2) dribbles against Cleveland Cavaliers guard Collin Sexton (2) in the first quarter at Quicken Loans Arena. Mandatory Credit: David Richard-USA TODAY Sports | USA TODAY Sports

Now that the LA Clippers/Aspiration saga is over, Kawhi Leonard is now a Toronto Raptor again. The two-time Finals MVP had a short, but memorable run with the Raptors back in 2019, leading them to their only championship in franchise history. Since Leonard’s exit to the Clippers, Toronto has been rebuilding their way back up to relevancy.

That path led them to an excellent 2025-26 season, where the Raptors unexpectedly went 46-36, going fifth in the Eastern Conference. Toronto then faced the Cleveland Cavaliers in the first round of the playoffs, losing in seven games.

But it was far from easy for the Cavs, who looked vulnerable after the first two games. The fully healthy Cavaliers went to seven games with a Toronto team, without starting point guard Immanuel Quickley and All-Star forward Brandon Ingram for much of the series.

May 3, 2026; Cleveland, Ohio, USA; Toronto Raptors forward Scottie Barnes (4) goes for a loose ball against Cleveland Cavaliers center Jarrett Allen (31) during the second half of game seven in the first round of the 2026 NBA Playoffs at Rocket Arena. Mandatory Credit: Ken Blaze-Imagn Images | IMAGN IMAGES via Reuters Connect

So what does Leonard’s Raptors reunion mean for the Cavs?

Well, it could mean they are in some trouble.

Toronto is bringing in Leonard, one of the league’s best playoff performers, to replace Brandon Ingram, who was a non-factor in the first round. 

Leonard also fits the Raptors’ style perfectly.

Apr 8, 2026; Inglewood, California, USA; Los Angeles Clippers forward Kawhi Leonard (2) reacts after a missed basket in the second half against the Oklahoma City Thunder at Intuit Dome. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | IMAGN IMAGES via Reuters Connect

Over the course of their rebuild, Masai Ujiri and Bobby Webster have targeted tall, long and athletic wings and forwards - Scottie Barnes, R.J. Barrett, Brandon Ingram, Collin Murray-Boyles. The two-time Defensive Player of the Year certainly blends into Toronto’s program, while still providing high-quality offense at an efficient level.

As crazy as it may seem, Leonard is coming off the best scoring season of his career. In his 14th playing season, the 35-year-old averaged 27.9 points, 6.4 rebounds and 3.6 assists, shooting 51% from the field, 39% from three and a career-best 89% at the charity stripe. Kawhi Leonard gives Toronto the closer they were missing.

A MASTERPIECE FROM KAWHI LEONARD!

🖐️ 55 PTS (career-high)
🖐️ 11 REB
🖐️ 5 STL
🖐️ 3 BLK
🖐️ 5 3PM

That ties the Clippers franchise record for PTS in a game 🔥 pic.twitter.com/PMacnRiUxW

— NBA (@NBA) December 29, 2025

Scottie Barnes Poised For Another Leap

The biggest reason for Toronto’s success last year was the leap that Scottie Barnes took. Although his counting stats do not jump off the page, it was clearly Barnes’ most effective campaign of his five-year career.

The 25-year-old posted career-highs in shooting from the field, three and the free throw line. His defense was astounding, showing his ability to guard all five positions at times.

Most importantly, Barnes played his best when the stakes went higher in the 2026 playoffs. Against Cleveland, he averaged 24.1 points, 6.1 rebounds, an astounding 8.6 assists, and increased shooting percentages from everywhere. That even includes 38% from three! He was doing it all for Toronto offensively, from scoring and shooting to making the right reads for his teammates.

May 1, 2026; Toronto, Ontario, CAN; Cleveland Cavaliers guard James Harden (1) battles with Toronto Raptors forward Scottie Barnes (4) during the third quarter in game six of the first round of the 2026 NBA Playoffs at Scotiabank Arena. Mandatory Credit: Nick Turchiaro-Imagn Images | IMAGN IMAGES via Reuters Connect

Then at the other end, Toronto asked Barnes to guard Cleveland’s All-Star backcourt. His defense was superb against Donovan Mitchell and James Harden, so much to the point that the Raptors nearly came back and won the series.

I believe Barnes has a very similar archetype and playstyle to Kawhi Leonard, while also having the vision of a point guard. Those two together should make for one of the best two-way duos in the NBA.

So how does Cleveland combat Toronto in both the regular season and a potential playoff rematch?

Apr 20, 2026; Cleveland, Ohio, USA; Cleveland Cavaliers guard Donovan Mitchell (45) talks with guard James Harden (1) during the first half during game two of the first round of the 2026 NBA Playoffs against the Toronto Raptors at Rocket Arena. Mandatory Credit: David Dermer-Imagn Images | IMAGN IMAGES via Reuters Connect

Continuity

The Cavs will have this advantage over many of their Eastern Conference competitors. Besides Peyton Watson (who appears to be a seamless fit at small forward), Cleveland does not have to spend a bunch of time fitting in new star players. In fact, they already had that process last spring.

Outside of Detroit and New York, the Cavaliers will have the most continuity in the East. It may take some time for Toronto to adjust to having Kawhi Leonard back on their team. After an incredible leap that Scottie Barnes took last season, will he be okay with Leonard becoming the top scoring option? Can Barnes take another step if Leonard or R.J. Barrett control the ball a ton?

Good Health

As much as Leonard poses a threat on the court, he has not been very durable over the last few seasons, only passing the 65-game threshold once since 2017. The Raptors will most likely look to load manage him throughout the year, much like they did in Leonard’s previous stint.

Cleveland’s regular season got off to such a rocky start, because of the nagging injuries. Much like every other team, the Cavs and Raptors will need as many reps of their starting five as possible.

Jan 20, 2024; New York, New York, USA; Toronto Raptors guard RJ Barrett (9) and guard Immanuel Quickley (5) shake hands before a game against the New York Knicks at Madison Square Garden. Mandatory Credit: Brad Penner-USA TODAY Sports | USA TODAY Sports via Reuters Connect

Frontcourt Has To Dominate

Toronto’s Projected Starters: Immanuel Quickley, RJ Barrett, Kawhi Leonard, Scottie Barnes, Jakob Poeltl

Cleveland’s Projected Starters: James Harden, Donovan Mitchell, Peyton Watson, Evan Mobley, Jarrett Allen

Defensively, Raptors coach Darko Rajakovic may go back to the strategy of throwing Barnes on either Cavalier guard. When it matters most, I could see Barnes guarding Mitchell and Barrett taking Harden with his size.

With that, Toronto will hope to hide the 6’2 Immanuel Quickley on Peyton Watson, then match their old school center, Jakob Poeltl, with Cleveland’s Jarrett Allen. That leaves Kawhi Leonard to guard Evan Mobley.

Cleveland’s strategy offensively could be to matchup-hunt, and just attack whoever Quickley is guarding. That includes Harden and Mitchell running pick-and-rolls with Watson to get Quickley in the action.

But if the Raptors defend the Cavs this way, Cleveland’s frontcourt needs to pull through. Kawhi Leonard’s post defense has declined slightly with his age. Evan Mobley would have a chance to play well down low, both as a post threat and a passer in the short roll.

Jarrett Allen dominated the Raptors in Game 7 last year, posting a double-double in the third quarter alone. Against either Raptors big, whether it’s Poeltl or impressive sophomore Collin Murray-Boyles, Allen has to win that matchup.

May 3, 2026; Cleveland, Ohio, USA; Moondog performs during the first quarter of game seven between the Cleveland Cavaliers and the Toronto Raptors in the first round of the 2026 NBA Playoffs at Rocket Arena. Mandatory Credit: Ken Blaze-Imagn Images | IMAGN IMAGES via Reuters Connect

Cavs-Raptors Regular Season Matchups

January 5 - 7:00 (Cleveland)

January 29 - 7:00 (Toronto)

February 9 - 7:00 (Cleveland)

February 12 - 7:30 (Toronto)

Final Thoughts

On paper, the Cavaliers are the more talented team. But will they be the tougher team when it matters? We’ll have to see. Both teams will be in the mix for a top four seed in the East.