The Los Angeles Clippers were on cloud nine when they signed Kawhi Leonard back in 2019, but things haven’t quite gone according to plan since. The Clippers haven’t had much success with Leonard and now find themselves embroiled in one of the biggest scandals in recent NBA history.
All of this has led to The Ringer’s Bill Simmons making quite an interesting claim about the Leonard signing on The Bill Simmons Podcast.
“The entire thing of going into business with this dude, 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… It’s already retroactively one of the worst trades of all time.”
Podcast guest Joe House disagreed with Simmons as he felt the Luka Doncic trade between the Dallas Mavericks and the Los Angeles Lakers deserves the top spot. While that was indeed an awful move by the Mavericks, this has the potential to be worse. Let’s see why.
It has been widely reported that one of Leonard’s conditions to sign with the Clippers was that they had to trade for Paul George from the Oklahoma City Thunder. George had just finished third in voting for MVP and DPOY in 2019, and his stock was at an all-time high at the moment. It was always going to take a massive haul to acquire him.
The Clippers would end up parting with Shai Gilgeous-Alexander, Danilo Gallinari, and five first-round picks for George. They also agreed to two first-round pick swaps. This was seen as a bit of an overpay, but the thought was that this would all be worth it if Leonard and George led the Clippers to glory one day. That wouldn’t happen, though.
The farthest the Clippers ever went in the Leonard and George era was when they made it to the Western Conference Finals in 2021. The former didn’t even play in that series against the Phoenix Suns, as he was out with an ACL tear.
George dropped the curtain on this era when he left for the Philadelphia 76ers in free agency in 2024. The Clippers won just three playoff series in the five seasons he was with them. This would have been disappointing regardless, but the haul they gave up made this all the worse.
Gilgeous-Alexander just won MVP in 2025 and led the Thunder to the NBA championship. Jalen Williams was his partner in crime, and he was selected with the 2022 first-round pick that they got from the Clippers. The Thunder should probably send a thank-you card to the Clippers for gifting them a title.
All this was bad enough, but we now get to the scandal. The Clippers have been accused of circumventing the cap by paying Leonard $28 million via Aspiration. The now-bankrupt environmental company gave the star what was essentially a no-show endorsement deal months after Clippers owner Steve Ballmer had invested $50 million in them.
The NBA could drop the hammer on Leonard and the Clippers if they are found guilty of cap circumvention. If the team does get slapped with harsh penalties such as losing multiple first-round picks, then you can very well make the case that signing Leonard ended up being the most damaging transaction of all time.
