Kawhi Leonard’s NBA contract extension with Raptors will look terrible in 2 years

The Toronto Raptors are betting on Kawhi Leonard long-term to lead them back to the top of the NBA .

On Tuesday, the Raptors and Leonard reached an agreement on a two-year, $115 million extension that could keep him in Toronto through the 2028-29 season. Leonard is coming off one of his best seasons in recent memory, averaging 28 points in 65 games for the Clippers last season.

But the Raptors are making a massive commitment to an aging player with a long injury list, and this contract could look very different two years from now. The contract extension is going to look terrible in years to come, and here's why:

The Raptors aren't contenders in the East

Apr 5, 2026; Sacramento, California, USA; LA Clippers forward Kawhi Leonard (2) before the game against the Sacramento Kings at Golden 1 Center. Mandatory Credit: Darren Yamashita-Imagn Images

Toronto improved this off-season by adding Leonard, but so did the rest of the Eastern Conference. Multiple teams in the Eastern Conference either jumped into contention or strengthened their already talented rosters.

The Knicks are coming off a championship, the Heat added Giannis Antetokounmpo , and the 76ers added LeBron James and Jaylen Brown . Cleveland also returns a core that reached the Eastern Conference Finals, while Detroit and Boston are both coming off 60-win seasons.

Toronto has Scottie Barnes , Kawhi, and a solid supporting cast, but that doesn't automatically put the Raptors in championship contention. If Leonard struggles to stay healthy, Toronto could find itself fighting for a spot in the play-in tournament.

This is where the contract could become a potential issue.

Leonard's extension doesn't begin until the 2027-28 season, when he'll be 36. He'll have aged even more and will be putting a massive hit on the salary cap, making it harder for them to acquire talent. This could be an issue, especially if Leonard begins to deal with injuries.

His contract extension will also make it harder to re-sign young talent and build around Scottie Barnes. The Raptors are taking a huge gamble on Leonard, hoping that his health and production will hold up.

That bet could pay off. If it doesn't, Toronto could be stuck with an expensive contract and limited flexibility just as the rest of the Eastern Conference gets better.