Kawhi Leonard, Raptors Advance Toward Contract Extension Days After Trade Clears Record NBA Penalties

TORONTO — The Toronto Raptors and Kawhi Leonard are engaged in advanced discussions on a contract extension that could pay the 35-year-old forward roughly $124 million over two years, according to a report Thursday from Jake Fischer of The Stein Line, relayed by Hoops Rumors. The talks come less than a week after a trade sending Leonard back to Toronto was finally completed, closing out a saga that spanned nearly three months and coincided with the most severe disciplinary action the NBA has ever taken against a franchise.

A Trade Three Months in the Making

The Raptors and Los Angeles Clippers agreed in principle to a deal centered on Leonard in late June, but the transaction was put on hold in July amid a league investigation into whether the Clippers had circumvented the salary cap. The trade was officially finalized on Monday, with Toronto sending forward Brandon Ingram, guard-forward Gradey Dick, unprotected first-round picks in 2031 and 2033, two second-round picks and a 2027 first-round pick swap to Los Angeles in exchange for Leonard. He waived a trade kicker worth roughly $7.45 million to help the deal fit under the league's restrictions.

It is Leonard's second stint in Toronto. He spent the 2018-19 season with the Raptors after arriving in a trade from San Antonio, leading the franchise to its first NBA championship and winning Finals MVP before departing for the Clippers in free agency that summer.

How the Scheme Came to Light

The violations trace to a previously undisclosed endorsement deal: a four-year, $28 million agreement Leonard signed with Aspiration Partners, a Clippers sponsor, in 2021. According to an account of the case's origins on Wikipedia's summary of the scandal, the arrangement first surfaced in reporting that traced a Leonard-linked limited liability company listed as a creditor in Aspiration's bankruptcy filings, combined with an anonymous interview with a former Aspiration employee who alleged the deal was designed to circumvent the cap. Leonard was not required to perform promotional work in exchange for the money — a "no-show" structure, in the description used by investigators — and had been paid roughly $1.75 million of it by the end of 2022, before Aspiration collapsed into bankruptcy.

NBA commissioner Adam Silver addressed the findings directly. "I am deeply disappointed by the flagrant violations of our rules and by the Clippers' institutional and leadership failures that led to this misconduct," Silver said in a statement accompanying the league's September 2 findings. "The severity of the penalties reflects the seriousness of the violations."

The Findings Behind the Delay

The trade's holdup stemmed from an independent investigation by the law firm Wachtell, Lipton, Rosen & Katz, whose findings the league released in a detailed statement on September 2. Investigators concluded the Clippers had violated the collective bargaining agreement's salary-cap circumvention rules by arranging off-court endorsement opportunities for Leonard with four companies doing business with the team — Aspiration Partners, Boingo Wireless, Daktronics and Lockton Insurance — and by covering personal expenses on his behalf. The league called it a pattern of misconduct by an organization it identified as a prior offender of the same rules.

The penalties, among the steepest in league history, included the forfeiture of five Clippers first-round draft picks from 2029 through 2033, a $30 million franchise fine and a five-year league compliance-monitoring program, a scope of punishment independently confirmed by NPR. Owner Steve Ballmer was suspended from all league and team activities for one year. President of business operations Gillian Zucker drew a one-year suspension without pay for what the league said was her direct culpability and for providing misleading statements to investigators, while president of basketball operations Lawrence Frank was suspended six months without pay. Leonard himself was fined $700,000, though his contract was not voided and he was not suspended. Dennis Robertson, Leonard's longtime business manager, was banned from NBA team business for five years.

"This has been a very difficult time for everybody associated with the Clippers, and for that, I have sincere regrets."

That was Ballmer's response, issued in a written statement on September 14 in which he said the organization had accepted the league's findings. "We have communicated to the NBA that we are complying with the penalties assessed by the league, have paid the fine, and are moving forward," Ballmer wrote in the statement, clearing the final obstacle to completing the trade.

Fitting In Beside Barnes, and a Void in Los Angeles

Leonard has been careful in his early comments in Toronto to cast himself as a complement to the team's incumbent star rather than its new centerpiece. Speaking to the Raptors after his arrival, he said 25-year-old forward Scottie Barnes is "going to be a problem this coming year," and made clear he does not intend to take over the offense. "If it's Scottie's team, it's his team," Leonard said. The framing matters for a Toronto front office that has built around Barnes as its long-term core, betting that Leonard's two-way skill set can slot alongside him rather than compete with him for touches.

In Los Angeles, the rebuild proceeds without Frank, who remains suspended, and largely without Ballmer for the next year. General manager Trent Redden, who was authorized to execute the Leonard trade, and senior basketball executive Mark Hughes are expected to handle day-to-day basketball decisions in the interim, while head coach Tyronn Lue remains in place. Despite the loss of five additional first-round picks on top of those surrendered in the trade itself, the Clippers have signaled they intend to compete for a playoff spot around Ingram and Dick this season rather than fully rebuild.

What Happens Next

Any extension for Leonard is constrained by the NBA's extend-and-trade rules and by the so-called Over-38 provision, which limits long-term deals for players who will be well into their late 30s by the contract's end; Leonard is set to earn $50.3 million in 2026-27, the final season of his existing contract, before any new deal would begin. Toronto has not confirmed the talks publicly, and no agreement had been signed as of Thursday afternoon.

On the court, the Raptors open the preseason on October 3 against the Miami Heat in what is set to be the first NBA game played in Quebec City, before opening the regular season at home against the Chicago Bulls on October 21. Leonard is scheduled to face his former team twice during the regular season, with the Clippers visiting Toronto on November 2 and the Raptors traveling to Los Angeles on January 1 — the first meetings between the two sides since the trade and the investigation that delayed it.