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“He’s a Gangster”: Stephen A. Smith Slams Kawhi Leonard on National Television After Raptors Trade

Sep 16, 2026, 6:40 AM CUT

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Earlier, Stephen A. Smith had demanded that the Clippers void Kawhi Leonard's trade entirely. He insisted that "your ass is gonna stay right there in L.A." rather than let Leonard walk away to Toronto with a fresh start. That demand went unanswered, as the trade has now officially been completed.

With the Clippers finalizing the deal, sending Leonard to the Toronto Raptors for Brandon Ingram, Gradey Dick, two first-round picks, a first-round swap and two second-round picks, Smith gave his take on the entire saga in blunt terms. 

"He's a gangster," Smith said on ESPN's First Take. "I mean, to sit up there, he broke the rules, got caught, pointed the finger at somebody else, threw the organization under the bus, got his money, and left the country. I mean, damn, how much better can it get than that?"

The label isn't really praise. It's Smith's way of describing an outcome he still clearly finds unjust, and at how favorably it broke for Leonard.

Each piece of Smith's rundown maps onto something that actually happened over the past year. The NBA's investigation confirmed that Leonard received improper compensation tied to his uncle, Dennis Robertson, who was banned from all NBA business dealings for 5 years as a result.

Leonard was fined just $700,000 in restitution. He avoided any suspension entirely and, per Shams Charania's reporting, had no prior knowledge of the salary circumvention scheme, a finding that effectively let him walk away from the league's harshest punishment in recent memory while the organization and its ownership absorbed nearly all of it.

The Clippers were fined $30 million and stripped of five future first-round picks. Owner Steve Ballmer was suspended for a year without pay. President of business operations Gillian Zucker was suspended for a year, and president of basketball operations Lawrence Frank was suspended for six months.

Against all that, Leonard completed a trade to a new team with his checkbook barely dented. "Kawhi Leonard got off easy," Smith said in an earlier segment. "He owes tens of millions of dollars for the amount of time he's taken off work... Kawhi Leonard should give master classes for how to get paid for not working."

After the league's ruling came down, Smith had called for the Raptors trade to be nullified altogether. He argued that Leonard should "suffer the consequences" in Los Angeles rather than get a clean exit to a new franchise.

Charania reported that the trade was cleared to proceed almost immediately once the investigation concluded.

For the Clippers, the trade closes out what Smith and others have repeatedly called one of the most damaging single-player sagas in recent NBA history.

Five years and one championship-caliber core built partly around a player now gone, with five first-round picks and $30 million in penalties as the lasting cost.

For Leonard, it means a fresh start in Toronto. The same city he delivered a championship to in 2019, arriving with his reputation dented but his career, and his money, fully intact, the exact outcome Smith's comments suggest he still can't quite believe the league allowed to happen.

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Ubong Archibong is an NBA writer at BasketballNews, bringing over two years of experience in basketball coverage. Having previously worked with BasketballNews, Sportskeeda and FirstSportz, he has developed a strong foundation in delivering timely and engaging content around the league. His coverage focuses on game analysis, player performances, and evolving narratives across the National Basketball Association. Blending statistical insight with storytelling, Ubong aims to go beyond the immediate headline by placing performances and moments within a broader context, helping readers better understand the dynamics shaping the game. His work prioritizes clarity, accessibility, and a fan-first approach that connects audiences to both the action and the personalities behind it. Before joining BasketballNews, Ubong covered the NBA and WNBA across multiple platforms, building experience in fast-paced reporting and deadline-driven publishing. His background in content writing has strengthened his ability to balance speed with accuracy, ensuring consistent and reliable coverage for a global audience.

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Tanay Sahai

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