Bill Simmons Has Strong Take on Clippers’ Kawhi Leonard Era

Simmons was quickly reminded of the Luka Doncic trade that took place during the 2024-2025 NBA season. Many have dubbed the swap between the Los Angeles Lakers and the Dallas Mavericks as one of the shocking and worst trades of all time, from the Mavs’ perspective.

As Simmons looks back, he acknowledged that at the very least, the Mavericks ended up with a star player in Anthony Davis, and an assumed superstar Cooper Flagg, who was selected No. 1 overall after the Mavericks got lucky in the NBA Draft Lottery.

“Forget all of the dumb reasons behind the trade, would you trade Anthony Davis and Cooper Flagg for Luka?” Simmons added.

When it comes to the Clippers, they moved a lot of pieces and did plenty of heavy lifting to kickstart the Kawhi era in 2019. At the time, Leonard was coming off a spectacular run with the Toronto Raptors. It was a stint that was short-lived, but it was clear that Leonard was one of the top players in the game.

With the Raptors, Leonard averaged 26.6 points, 7.3 rebounds, and 3.3 assists in 60 games. During the playoffs, Leonard played 24 games for the Raptors, averaging 30.5 points, 9.1 rebounds, and 3.9 assists. He made 49 percent of his shots from the field as the Raptors went on to win the NBA Championship. Kawhi was the NBA Finals MVP for the second time in his career.

The Clippers bet big on Kawhi initially with a reported three-year deal, which was worth over $100 million. They were urged to land Paul George, as Leonard wanted to form a superteam with the star wing. The Clippers traded Shai Gilgeous-Alexander, Danilo Gallinari, and five first-round picks in order to land George. In hindsight, it was the wrong move.

Beyond the investigation, which suggests Kawhi got a lot more than a few contract extensions, the Clippers didn’t have any notable success during the Paul George era. The Clippers went five seasons with George on the court, and didn’t make the NBA Finals once.

George signed with the Philadelphia 76ers in 2024-2025, leaving the trio of Leonard, James Harden, and Norman Powell to try and get it done for LA in the playoffs. The Clippers were bounced early, adding another disappointing season to the Leonard era in LA.

Meanwhile, the Thunder won the NBA Finals in 2025. Shai Gilgeous-Alexander was also crowned the league’s MVP. Without making that trade, the Clippers could feel much better about where they at as an organization, even with the investigation going on. It could’ve been an easy transition away from the Leonard era, giving the keys to SGA.

Instead, the Clippers are banking on winning a title with a 34-year-old Kawhi, who has struggled to stay healthy long-term. Sometime soon, the Leonard era will be over for the Clippers, and they don’t have a quick and easy transition into a new phase. A full-blown rebuild could be on the horizon for the Clippers, and depending on their punishment (if there is one), the Clippers could end up losing some key assets.

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