Kawhi Leonard‘s second act with the Raptors now has a contract to match. Leonard agreed to a two-year, $115 million extension with Toronto, plus a player option for 2028-29, his agent Harrison Gaines told ESPN. The news broke on September 22, 2026, and it settles one of the strangest offseason sagas in recent NBA memory.
The numbers
Counting the extension, Leonard now has three years and $165 million on his Raptors deal. He gave up some money to get it done. He took $11 million less than his maximum extension and waived a $7.45 million trade kicker as the two sides worked around the Raptors’ rising payroll.
The length of the deal comes from his age. The over-38 rule capped the extension at two years, but Leonard can sign a multi-year contract in 2028 if he still has the value to command one. The player option gives him a way to test that market.
The deal also uses up much of Toronto’s flexibility. Before it, the Raptors had roughly $87 million of luxury tax room heading into 2027-28, and Leonard’s salary will take up most of it.
How he got here
Leonard arrived in Toronto through a trade that took months to finish. The Clippers first agreed to send him to the Raptors on June 30 for a package that included Brandon Ingram, Gradey Dick, and picks, but the deal wasn’t finalized until September. That trade came after a year of turmoil around the Clippers. The NBA’s cap circumvention investigation over Leonard’s endorsement deals ended with the Clippers losing five first-round picks and paying a $30 million fine, while Leonard was fined $700,000 and not suspended.
Leonard also reshuffled his business team. He fired Robertson and agent Mitch Frankel in June and hired Gaines a few weeks later. The NBA has banned Robertson from all business dealings.
Other teams were interested. Minnesota and Detroit both wanted to trade for him and extend him in June, but with one year left on his old deal Leonard had leverage and preferred Toronto.
Why Toronto
The reunion has a good story behind it. Leonard led the Raptors to the franchise’s only championship in 2019, then left for the Clippers the following summer. Seven years later, he expects to finish his career in Toronto, and the two sides have been talking about his long-term future since July.
The bet is on a player who is still producing. Leonard is older and has dealt with injuries, but he averaged 27.9 points, 6.4 rebounds, 3.6 assists and 1.9 steals in 65 games last season with the Clippers. He is now 35, and the health question that has followed his career hasn’t gone away. Toronto is committing real money to a player whose availability has never been guaranteed.
The bigger picture
The contract also says something about the market. With Kevin Durant and Leonard both signing for less than the max, the market appears to have reset for players in their late 30s. That puts pressure on the next star in line, and CBS Sports pointed to Stephen Curry and the Warriors as the obvious example.
For Toronto, the questions are about the roster and the standings. The Raptors face a stacked Eastern Conference, though pairing Leonard with Scottie Barnes should keep them in the mix. Leonard is signed through at least 2028, and he doesn’t have to be the player he was in 2019 for that to work. The Raptors mostly need him on the floor and close to what he showed last season. If he stays healthy, this could be one of the better pieces of business of the offseason. If not, Toronto has spent a lot of its future flexibility on him.
Leave a Reply