Six years ago, in the summer of 2019, the NBA witnessed one of the wildest offseasons in its history. Many superstars decided to team up to chase an NBA title and one of the biggest of that summer was the pairing of Kawhi Leonard and Paul George with the Los Angeles Clippers .
At that moment, Leonard looked like the best player in the league, having almost single-handedly delivered the Toronto Raptors their first championship in franchise history while winning the Finals MVP. Alongside Leonard, George was considered one of the best two-way players in the NBA.
Still, looking back, Bill Simmons feels the two teaming up is probably the worst deal in NBA history.
"This whole Kawhi thing, getting into business with him, all the stuff it cost the Clippers, all the players and Draft picks, plus this scandal with Leonard," Simmons said. "It has to be the most damaging transaction in NBA history. I can't even compare it to anything else, honestly. It's already retroactively one of the worst trades of all time."
Although the word "worst" may sound a bit too hard, when you look at the fact that the Clippers gave up Shai Gilgeous-Alexander , Danilo Gallinari and several first-round picks in those trades — one of which turned into Jalen Williams — Simmons' words carry real weight.
Gilgeous-Alexander and Williams eventually became the leading duo that delivered the Oklahoma City Thunder their first championship in franchise history. Immediately after the season, they both received max contracts, and many already think of them as the leaders of another dynasty in the making.
On the other hand, Leonard only deepened his struggles with injuries, missing a total of 137 regular season games over five years. Although he still looked like an older version of his peak self whenever he played, the superstar forward missed too much time for the Clippers to make a real run at the Larry O'Brien Trophy.
Just a few days ago, ESPN's Baxter Holmes reported that the Clippers are done with Kawhi once his contract expires .
"Multiple GMs and other league executives said they expect Leonard to play out his contract with the Clippers, which is set to end after the 2026-27 season. But even then, one former staffer said, the organization's focus has shifted. 'They're done building around [Kawhi],' he said. 'They know that and he knows that,'" Baxter reported .
The final straw was certainly Leonard's circumvention of the salary cap through sponsorship deals. New reports about the case are coming out every day, and it's becoming increasingly clear that both the Clippers and Leonard will face heavy fines.
Still, it's hard to blame the Clippers for going after Leonard in 2019. After all, he was arguably the best player in the league at the time, coming off a historic postseason run in his lone season in Toronto. He was also relatively healthy, having played 60 regular season games and 24 out of 25 games in the playoffs with the Raptors.
Nobody could have predicted that Gilgeous-Alexander would reach the level he's at today. Nobody could have predicted that Leonard and George would miss so much time, especially in crucial moments of the season. But that's the reality the Clippers have faced. And it might be time to start over.
This story was originally reported by Basketball Network on Sep 20, 2025, where it first appeared in the Latest News section. Add Basketball Network as a Preferred Source by clicking here.
