
Kawhi Leonard could just be counting down the days before the Toronto Raptors tender him a contract extension after returning to the franchise this offseason.
However, NBA analyst Tim MacMahon of ESPN is warning the Raptors of possibly absorbing Leonard’s baggage once they commit to him in the foreseeable future.
ESPN Analyst Warns Toronto Raptors About Kawhi Leonard

According to MacMahon, signing Leonard to a contract extension could mean bad news for the Raptors, considering Leonard’s health history and durability as he enters his late 30s.
“The risk that the Raptors are taking with Kawhi has nothing to do with this entire investigation. It’s just Kawhi Leonard with his durability issues in his mid-30s, and you’re about to give him a fat extension. Like, how is that going to age?” said MacMahon on the Hoop Collective podcast.
Leonard is currently eligible to sign a two-year max contract extension worth up to $126.1 million with the Raptors. That would keep him under contract through the 2028-2029 season.
Following his trade back to Toronto, both sides have engaged in advanced discussions and are reportedly nearing an agreement on the extension.
Leonard’s current contract would earn him $50.3 million for the 2026-2027 NBA season, the final year of his previous deal.
Since joining the Clippers in 2019 through the 2025-2026 season, Leonard’s availability had been impacted by health issues.
His most notable absence was missing the entire 2021-2022 season recovering from a partial ACL tear in his right knee suffered during the 2021 postseason.
He has also dealt with right knee stiffness, foot sprains, and ankle injuries that regularly sidelined him for stretches of seasons throughout his Clippers tenure. Leonard missed roughly 40% of possible regular-season games during his time in Los Angeles.
Nevertheless, Leonard is coming off a relatively healthy season. Leonard appeared in 65 games and averaged a career-high 27.9 points per game to lead the Clippers en route to him being named to the All-NBA Second Team.
Kawhi Leonard Loves To Be In Toronto

Kawhi Leonard has grown to love Toronto after playing for the Raptors in 2019 and leading them to their first-ever NBA championship.
In a video posted by the team, Leonard opened up about playing again with the Raptors.
“I’m not really championship chasing… I didn’t want to put on a thousand jerseys,” Leonard said. “This city took a liking to my family, and I took a liking to this city. I really liked it. My son was born here, and he’s been asking me forever when he’s going to come back. Now he’s back, and he’s able to see it rather than me tell him the great stories that happened.”
“This city always gave me love and showed support from everybody. I’m happy that they love what I did here. I gave this city everything. I was coming in that year injured, and I just gave them my all,” Leonard added.
Now at 35 years old, Leonard is coming in as the team’s leader as he looks to steer the Raptors’ young core led by Scottie Barnes to greater heights next season.
Last season, the Raptors finished sixth in the regular season but lost in seven games in the first round against the Cleveland Cavaliers, a team that went on to the Eastern Conference Finals.
Potential Bad News Warns Raptors About Signing Kawhi Leonard To New Contract