Of course, the LA Clippers have been making headlines with the NBA investigating their situation with Kawhi Leonard's "no-show job" with Aspiration. However, many people are starting to look back to question whether the Clippers' biggest mistake came in 2019.
In the 2019 offseason, Kawhi Leonard was coming off a legendary championship run with the Toronto Raptors, becoming one of the most highly anticipated unrestricted free agents in recent NBA memory. Leonard's top three destinations became the Clippers, Raptors, and Los Angeles Lakers, but ultimately, Steve Ballmer and company won the Kawhi sweepstakes.
There were some concerns about how legitimate the Clippers' signing of Leonard was, and questions about whether or not there were some under-the-table agreements between the two, but regardless, the superstar forward was a Clipper.
Through six years in LA, Leonard has played over 60 games just once, including the 2021-22 season that he missed entirely. Leonard's health seems to always be a concern, and now these Apsiration accusations have backed the Clippers into a tight corner completely.
Since Leonard signed with the Clippers, the team has made one Western Conference Finals appearance in 2021, but has not gotten past the first round since. The Leonard-led Clippers have seen minimal success, especially relative to what they had to give up to make it happen.
Greatest trade in OKC Thunder history:
— Jake Weinbach (@JWeinbachNBA) June 23, 2025
• Clippers
Paul George
• Thunder
Shai Gilgeous-Alexander
Danilo Gallinari
2021 first-round pick via MIA (Tre Mann)
2022 first-round pick via LAC (Jalen Williams)
2023 first-round pick via MIA
2023 first-round pick swap via LAC
2024…
As part of Leonard's request from the Clippers before he signed, he wanted the franchise to trade for Paul George, who was coming off an MVP-caliber season with the OKC Thunder. However, it turned out to be one of the most lopsided trades in NBA history, especially after Shai Gilgeous-Alexander won both NBA MVP and Finals MVP last season.
The Ringer's Bill Simmons recently called the Clippers' decision to sign Kawhi Leonard the most "damaging transaction in the history of the league."
"The entire thing of going into business with [Leonard], all the stuff it cost them, all the players and the draft picks, plus this scandal. It has to be the most damaging transaction in the history of the league," Simmons said. "I don't even think you could compare it to anything."
Will the Clippers' Kawhi Leonard signing go down as one of the most damaging NBA transactions? pic.twitter.com/TBP0k34tHo
— The Ringer (@ringer) September 19, 2025
Simmons' podcast guest, Joe House, brought up how the Dallas Mavericks' decision to trade Luka Doncic to the Los Angeles Lakers is worse, but Simmons held his ground.
"[The Mavericks] end up with Cooper Flagg. In a roundabout way, it somehow worked out," Simmons said. "Just forget all the dumb reasons behind the trade. Would you trade Anthony Davis and Cooper Flagg for Luka?"
Of course, when the Mavericks traded Doncic, the NBA was sent into a frenzy immediately. The Clippers' decision to trade for Paul George and bring in Leonard was not as devastating at the time, but over the last few years, it has grown into one of the worst things the franchise could have done, with no success to show for it. Still, time will tell if the Doncic trade is on that same level or not.
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