Kawhi Leonard has hired new representation ahead of contract extension talks with the Toronto Raptors, bringing in a new agent to oversee negotiations as he prepares to begin what he envisions as the final chapter of his career with the franchise he led to its only NBA championship in 2019.
Leonard’s new agent, who has worked closely with him over the past year as his business attorney, will meet with Raptors officials in Toronto in the coming days to discuss a potential extension. Leonard has one year and $50.3 million remaining on his current contract and is eligible to sign a new deal worth up to two years and $123.7 million with his new team.
A trade that Leonard shaped with his preferences
The trade that brought Leonard back to Toronto from the LA Clippers was agreed on June 30, with the Clippers receiving Brandon Ingram, Gradey Dick, two unprotected future first-round picks, a first-round pick swap, and two second-round picks in exchange for Leonard. The deal cannot be officially processed until Monday.
What made the trade possible was Leonard’s explicit decision to steer his own market. When the Clippers began exploring trades with multiple teams ahead of the NBA draft, Leonard communicated clearly that he would only sign an extension with Toronto. That position effectively removed other interested franchises from the conversation, as teams unwilling to acquire a player on a one-year contract without a commitment to stay had no viable path to making a deal work.
According to sources, three factors drove Leonard’s openness to returning to Toronto. He has familiarity with and trust in the organization’s front office leadership, which has remained largely intact. He genuinely enjoys the city. And he believes the Raptors can compete for a championship in the Eastern Conference.
Making history with the return
Leonard’s reunion with the Raptors places him in notable company historically, making him the 53rd player in NBA history to win a championship with a team, go elsewhere in the league, and then return to that original franchise. What makes his case distinctive is the level at which he was still performing immediately before the move back. No player in any of the previous 52 such reunions averaged 20 points per game immediately prior to rejoining the team where they won their title.
Leonard averaged 27.9 points per game for the Clippers last season, his best year in terms of individual production since his 2018-19 season in Toronto, when he averaged 28.5 points per game during the championship run. He is 35 years old and has managed his playing time and health carefully throughout his career, giving him a realistic chance of contributing at a high level for the duration of a two-year extension if the deal is reached.
The representation change and the investigation backdrop
Leonard’s decision to change agents represents a significant shift in how he manages his professional affairs. He previously worked with representation that had handled his negotiations with the Clippers, including a three-year extension signed in 2024.
The change comes as the Clippers remain under NBA investigation regarding whether the organization circumvented the salary cap through a corporate endorsement arrangement that involved Leonard. The investigation, conducted by an independent law firm, has not produced any formal findings. Leonard has denied any wrongdoing, and the investigation’s outcome is separate from his move to Toronto and the extension discussions underway there.
The Raptors extended their head coach on a multiyear deal amid the Leonard return, signaling an organizational commitment to building around the incoming star for a period that both sides appear to view as long-term rather than transitional.
