With Kawhi Leonard's trade back to the Toronto Raptors officially completed Monday, ESPN personality Stephen A. Smith delivered a strong reaction to how the star forward departed the Los Angeles Clippers following the NBA's investigation into the franchise.

During Tuesday's episode of “First Take,” Smith labeled Leonard a “gangster” while discussing the penalties handed down to the Clippers and Leonard before the blockbuster trade became official.

“For him to cause all the trouble that he’s caused for this organization and to walk away with nothing more than having to surrender $700,000 worth of restitution, is a crime,” Smith said. “Kawhi Leonard… he’s a gangster. 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?”

Smith's comments came after the NBA concluded its investigation and issued significant punishment to the Clippers two weeks ago. Los Angeles was fined $30 million and stripped of five future first-round draft picks, while owner Steve Ballmer received a yearlong suspension. Leonard was fined $700,000.

"Kawhi Leonard… he's a gangster. 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" – Stephen A. Smith pic.twitter.com/eRoy3uTLpt

— Awful Announcing (@awfulannouncing) September 15, 2026

The penalties cleared up the investigation that had previously left Leonard's future and a potential trade to Toronto in limbo. Thirteen days after the ruling, the Raptors and Clippers officially completed the deal.

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Kawhi Leonard returns to Raptors in blockbuster Clippers trade

Toronto acquired Leonard in exchange for Brandon Ingram, Gradey Dick, two unprotected first-round picks, one first-round pick swap and two second-round picks. The package gives Los Angeles two established players and significant draft capital as the franchise begins moving forward without Leonard.

The trade also brings Leonard back to the organization where he experienced the greatest success of his NBA career. Toronto originally acquired Leonard from the San Antonio Spurs before the 2018-19 season.

Leonard spent only one season with the Raptors but led them to their first NBA championship. Toronto defeated the Golden State Warriors in six games in the 2019 NBA Finals, with Leonard earning his second Finals MVP award.

He then left Toronto in free agency to join the Clippers, beginning a seven-season tenure in Los Angeles that ended under drastically different circumstances.

Leonard now returns to Toronto ahead of the 2026-27 season, while the Clippers move forward with Ingram, Dick and additional draft assets. For Smith, however, the circumstances surrounding Leonard's departure stood out just as much as the blockbuster return to the Raptors.