TORONTO — Harrison Gaines did not walk into this negotiation by accident. Leonard hired the agent in July, two months before the NBA formally approved his trade to Toronto, and the timing was its own kind of statement: Gaines was not retained to manage the exit from Los Angeles. He was brought in to handle what comes next. That work is now underway. The Toronto Raptors and Kawhi Leonard have held what league sources described as “advanced discussions,” with both sides nearing an agreement on a contract extension, NBC Sports reported Wednesday. Leonard is eligible for up to two years and $126 million. The number is still being resolved.
That gap between the maximum the collective bargaining agreement permits and what the Raptors are prepared to commit is the only remaining obstacle. Multiple reports indicate Toronto is targeting something notably below $100 million for two years. For a 35-year-old with Leonard’s medical history, that reluctance is not posturing. It is the question the Raptors have to answer before they sign anything: which version of Kawhi Leonard are they actually buying?
Last season offered the Raptors their most encouraging evidence in years.
Kawhi Leonard averaged 27.9 points over 65 games for the Clippers—the highest scoring average of his career and his healthiest season since 2018–19, when he led Toronto to its first NBA championship.
For Leonard, 65 games is significant. He has reached that mark only three times in 11 seasons. His other absences have included a torn ACL that cost him two full seasons, a knee procedure that erased another, and a thumb injury that limited a fourth.
Toronto is not simply buying 27.9 points on faith. The Raptors are weighing those 65 games against a career defined as much by the games Leonard missed as by what he produced when available.
That production remains difficult to replace. Leonard shot 38.7 percent from three-point range on substantial volume last season, continued defending at a level that earned him assignments against top opposing scorers, and repeatedly raised his play in close games.
For a Raptors team whose preseason begins October 3, those late-game situations are precisely what its championship hopes will require.
The Raptors paid for that access already. The trade package to Los Angeles included Brandon Ingram, Gradey Dick, two unprotected first-round picks in 2031 and 2033, a 2027 first-round swap, and two second-rounders, assets representing years of organizational inventory. The NBA approved that trade on September 14, closing a months-long administrative pause caused by the league’s salary cap investigation into the Clippers. That investigation concluded with five stripped first-round picks and a $30 million fine against owner Steve Ballmer, the largest franchise penalty in league history. Once that ruling landed, the final obstacle cleared. Leonard was in Toronto. Now the question is for how long.
The extension, if completed, would not begin until the 2027-28 season. Leonard is earning $50.3 million this year in the final year of his Clippers contract, and any extension signed now would run through 2028-29. Two years: his age-36 and age-37 seasons are what the Raptors are pricing. The disagreement is not about the term. It is about whether those particular seasons are worth approaching $126 million or something closer to a figure that accounts for what a body like Leonard’s has absorbed over eleven professional years.
“I didn’t want to put on a thousand jerseys,” Leonard said in a Raptors video released last week, speaking publicly for the first time since his return. He came back, he explained, because his son was born in this city and because he wanted to contribute to Barnes’ development rather than redirect the franchise around himself. “I just want to win.” That framing does not resolve the number. What it signals is that Leonard walked into Toronto with a specific intention, not a one-year audition.
The agent hire carries the same message. Gaines was brought in specifically for the Toronto chapter. An agent retained for an exit phase is a different conversation. What Gaines and the Raptors front office are now engaged in is a negotiation about what two more years of Kawhi Leonard costs, and whether the figure Toronto has in mind and the figure Leonard’s camp believes reflects his market value are close enough to sign.
They are close enough, sources told NBC Sports, to call the talks advanced. What remains unresolved is the precise distance still separating them.
