The biggest story of the NBA offseason wasn’t whether stars would re-sign with their teams or move to new squads, or which draft picks might turn into the next generation of elite talent. Instead, it was the fallout of the Aspiration situation involving the Los Angeles Clippers, Steve Ballmer, and Kawhi Leonard.
A quick refresher: Leonard signed a four-year, $28 million endorsement deal (that was actually worth up to $48 million) with a company called Aspiration, which sponsored the Clippers. Upon investigation, this appeared to be a “no-show” job for Leonard, and it seemed the Clippers were actually using this deal to funnel additional money to Leonard beyond what the team could do through the NBA’s salary cap. In total, four sponsorship deals carried as much as $66 million in potential compensation, including $18 million that was confirmed to be paid to Leonard. All of them violated the NBA’s salary cap circumvention rules.
The punishment for the Clippers was steep. Ballmer was fined $30 million, and the team has to forfeit five first-round draft picks. They’re likely going to struggle for a long time. However, Leonard emerged from everything fairly unscathed: He was fined $700,000 but did not receive a suspension, so he won’t miss any playing time due to a league punishment.
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In fact, Leonard got out of Los Angeles entirely. Earlier this month, the Clippers traded him to the Toronto Raptors—where he famously led the team to a 2019 title during his lone season in Canada—for Gradey Dick, Brandon Ingram, two first-round picks in 2031 and 2033, two second-round picks in 2030 and 2033, and a first-round pick swap next year.
And now, Leonard has signed a two-year contract extension with the Raptors worth $115 million. The deal includes a player option for the 2028-29 season. Leonard, 35, is entering this season on the final year of his Clippers deal, so he’s under contract for $165 million over the next three seasons. His plan is to finish his career in Toronto.
Interestingly, Leonard could have made even more. According to ESPN, he agreed to take $11 million less than the maximum extension Toronto could have given him, with the two sides discussing the move as a way to give the Raptors more flexibility with their growing payroll. Leonard also separately waived a $7.45 million trade kicker connected to his move from Los Angeles to Toronto.
In other words, after years of scrutiny over whether the Clippers found creative ways to funnel Leonard money outside the salary cap, Leonard’s return to Toronto actually involved him voluntarily leaving millions of dollars on the table. He still has $165 million guaranteed over the next three seasons, but apparently maximizing every available dollar wasn’t his priority this time.
Though Leonard’s on-court career has been mired by injuries, he’s coming off his highest-scoring season ever. Last year, he averaged 27.9 points in 65 games, though it didn’t translate into a postseason appearance. He’s still one of the league’s top defenders and has made seven All-NBA teams while winning two championships and two Finals MVPs in 2014 (with San Antonio) and 2019 (with Toronto).
Could Leonard help the Raptors return to postseason glory and earn another championship for the franchise? That remains to be seen, but signing a $115 million deal makes that $700,000 fine feel incredibly insignificant.
