The Toronto Raptors’ trade for Kawhi Leonard is official as the 2019 Finals MVP returns to the North ahead of the 2026-27 season. Leonard returns to the Eastern Conference, where a handful of teams have made major roster changes this summer, including the Philadelphia 76ers, Detroit Pistons, Cleveland Cavs, and Miami Heat. The Raptors followed suit by bringing Leonard back.

But how do they stack up against the defending champion New York Knicks and the aforementioned three teams, positioned to reach the upper echelon of the Eastern Conference standings? Looking to build off their first playoff appearance in four years, the Raptors’ reunion with Leonard is a step in the right direction. Still, outperforming three out of the four teams that finished the 2025-26 season with better records will be a challenge.

The Raptors’ 46-36 mark was the fifth-best record in the Eastern Conference standings last season. However, the 76ers’ trade for All-NBA forward Jaylen Brown and All-Star LeBron James should re-enter Philadelphia into the top tier for the first time since 2022-23. Roster depth is critical, as the Sixers also added Dean Wade, Kentavious Caldwell-Pope, and Anfernee Simons to their supporting cast for Brown, James, All-Star Tyrese Maxey, Joel Embiid, and budding star VJ Edgecombe.

The Cavs, who sent the Raptors home in their opening-round series of last season’s playoffs, are entering their first full season with James Harden. After a 4-0 sweep in the Eastern Conference Finals by the hands of the Knicks, Cleveland acquired 3-and-D specialist Peyton Watson. Harden and Watson both signed long-term deals.

Toronto’s newly formed trio of All-Star Scottie Barnes, RJ Barrett, and Leonard will be an intriguing counter to the Cavs’ All-Stars Donovan Mitchell, Evan Mobley, and Harden. However, shooting could prove to be the difference, along with how Raptors’ Collin Murray-Boyles looks after an impressive rookie season. Murray-Boyles has the potential to evolve into the best defender of his draft class.

He’s also an efficient scorer, averaging 8.5 points on 57.9% shooting, including 34% from deep last season. If Murray-Boyles can improve his 3-point touch, it’ll go a long way for the Raptors, but he’s on track to become a double-digit scorer. Immanuel Quickley connected on 37.4% of his 3-point attempts last season, which could spike up with Leonard back in the fold.

The Pistons prioritized shooting and flexibility during the offseason, adding sharpshooter Isaiah Joe, John Collins, Taurean Prince, and Gary Harris while parting ways with Isaiah Stewart, Caris LaVert, and Tobias Harris. The Pistons won their season series, 2-1, against the Raptors in 2025-26. Detroit’s depth was a significant advantage, and it could be again.

Could Kawhi Leonard, 35, close the Raptors' gap? He made the All-NBA Second Team for the first time in two years, averaging 27.9 points, 6.4 rebounds, 3.6 assists, and 1.9 steals for the LA Clippers last season. And what could be more motivating than coming back to the city he led to its first and only championship in 2019? Kawhi hasn’t come close to competing for a title since.

As for the Heat, which gutted its supporting cast for two-time MVP Giannis Antetokounmpo and joined forces with Bam Adebayo and Andrew Wiggins, the Raptors’ star-studded trio gets the edge on paper; Miami also signed four-time champion Klay Thompson. However, Barnes and Barrett are on the cusp of entering their prime, which takes the weight off Leonard, who led the Clippers to one of the greatest regular-season turnarounds in NBA history last season.

The defensive tandem of Leonard and Barnes makes the Raptors' upcoming games against the 2026 Finals MVP Jalen Brunson and the Knicks all the more intriguing. It'll be fascinating to see if Toronto can draw first blood in a pair of matchups against the defending champions in the first two weeks of the regular season.

While the Raptors, who will host the Heat, Clippers, and the Knicks before heading to New York and Detroit in their first two-game stint on the road, could start slow out of the gate, Toronto is talented enough to secure a top-5 seed. And in a best-of-7 series, with positive momentum in the final month of the regular season, could make a deep playoff run in 2027.

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Marc Spears’ honest take on Raptors’ Kawhi Leonard's upcoming season

Toronto Raptors forward Kawhi Leonard (2) celebrates with the Larry O'Brien Trophy after the Golden State Warriors in game six of the 2019 NBA Finals at Oracle Arena.
Kyle Terada-USA TODAY Sports

The Raptors pushed the Cavs to seven games in the first round of last season’s playoffs, which was the kind of experience Scottie Barnes and RJ Barrett can build off, considering the Cavs went on to compete in the Eastern Conference Finals. Kawhi Leonard’s championship pedigree of winning the 2014 Finals with the Spurs came in handy in 2019. The Raptors are hoping he can do it again.

While Leonard and the Raptors may not be considered favorites to win the Eastern Conference this upcoming season, they could be a dark horse worth keeping an eye on in 2027, according to ESPN’s Marc Spears.

“I saw the Toronto Raptors when they lost to the Cleveland Cavaliers, but they took them to seven games. This was certainly a team on the rise without Kawhi,” Spears said. “Scottie Barnes, RJ Barrett, and a lot of young talent. Now, Kawhi gets to go back to the Six and teach them how to win. Are they the favorites in the East? No. Are they scary in the East? Yes, I definitely think they are.”

Although the Raptors could be a year or two away from competing for a title, their short-term trajectory could push them closer to the Eastern Conference Finals sooner than most expect.