Winner: Kawhi Leonard. Loser: LA Clippers.

UPDATE • SEPTEMBER 22, 2026: Kawhi Leonard has agreed to a two-year, $115 million extension with Toronto, according to ESPN reporting confirmed by multiple outlets. The deal includes a player option for 2028-29. Combined with the final year already on his contract, Leonard now has three years and $165 million tied to the Raptors.

Winner: Kawhi Leonard

Kawhi Leonard just had arguably one of the best individual seasons of his career. He averaged 27.9 points, 6.4 rebounds and 3.6 assists in 65 games while nearly joining the 50/40/90 club.

And somehow, maybe even more importantly...

He actually played 65 games!

The Clippers moved the 35-year-old Kawhi while his value was still high, and now he heads back to Toronto — the place where he won his most recent championship.

Kawhi may not be as explosive as he once was. He may not be the same terrifying defender he was during his prime. But let’s not get it twisted: he is still one of the best players in the world.

His Clippers tenure will probably always be remembered as one big “what if?” What if Kawhi and Paul George stayed healthy? What if that group actually reached its ceiling? What if the Clippers didn’t mortgage so much of their future to build that team? And, of course, what if Shai Gilgeous-Alexander never left?

Kawhi never brought a championship to LA, but this move back to Toronto feels completely different. There isn’t the same pressure. This feels more like a celebration.

In one season, Kawhi delivered Toronto its first championship and became one of the most beloved players in Raptors history. That’s why he could win a title there, leave after one year for Los Angeles — and somehow still be loved in Toronto.

Now he gets to return without having to prove anything.

Toronto Made It More Than A Reunion

And now the story has changed again. This is no longer just Kawhi coming back for one nostalgic season. Toronto has made a real commitment.

Leonard has agreed to a two-year, $115 million extension that includes a player option for the 2028-29 season. With the final year of his existing deal included, he now has three years and $165 million connected to Toronto.

That tells you how the Raptors view this move. They did not give up Brandon Ingram, Gradey Dick and draft capital just to rent Kawhi for a year. They believe the version of Leonard who averaged 27.9 points last season can still be the veteran star who raises the ceiling of a young team built around Scottie Barnes.

There is obvious risk. Kawhi is 35, his injury history is real, and this deal takes him deep into his late 30s. But Toronto also knows exactly what a healthy Kawhi can mean to a franchise. The first time around, one season ended with a parade. This time, the Raptors are betting on more than one run.

This ain’t a one-year nostalgia tour anymore. Toronto is telling Kawhi: finish it here.

Kawhi is da fuckin GOAT!! No wonder this man has been outside more this summer than we’ve ever seen him. 😂

Loser: LA Clippers

Read the Kawhi section above for about 95% of why the Clippers are here.

For the other 5%?

Ask Pablo Torre. Lol.

But seriously, what happened to the Clippers this summer goes way beyond losing Kawhi Leonard.

On September 2, the NBA announced the results of an independent investigation and concluded that the Clippers violated the league’s salary-cap circumvention rules through off-court income arrangements connected to Leonard.

The league’s findings said the Clippers initiated off-court income opportunities between Leonard and companies doing business with the team, facilitated endorsement arrangements, offered team business connected to some of those deals and failed to report improper solicitations made on Leonard’s behalf.

The Bill Came Due

5 picks

The Clippers forfeited one first-round pick in each draft from 2029 through 2033.

$30M

The franchise was fined $30 million.

1 year

Owner Steve Ballmer was suspended from all league and team activities for one year.

5 years

The organization was placed under a five-year league compliance and monitoring program.

$700K

Leonard was required to pay the league $700,000.

Ballmer came into Los Angeles with unlimited enthusiasm, unlimited money and championship expectations. He got Kawhi. He got Paul George. He built Intuit Dome. He spent. He screamed courtside. He did everything possible to make the Clippers feel like a serious operation.

And yet the Kawhi era ends without a Finals appearance, with SGA becoming a transcendent star somewhere else, and now with five future first-round picks gone.

That’s a hell of a bill to pay for an era that never even produced a Finals trip.

Kawhi escaped the scene like nothing happened. 😂

4DK Verdict

The Kawhi era was already going to be remembered as one of the NBA’s greatest “what if?” stories. Now it has an investigation attached to it too — while Kawhi’s next chapter keeps getting better.

No championship. No Finals appearance. SGA became a superstar somewhere else. Kawhi went back to Toronto, and Toronto immediately committed another two years and $115 million to him. Five first-round picks disappeared. And Steve Ballmer got sent home for a year.

Yeah... the Clippers lost the offseason. And Kawhi may have won it even bigger than we first thought.

Reporting note: Investigation findings and penalties are based on the NBA’s official Sept. 2, 2026 announcement. Contract-extension terms are based on Sept. 22 reporting from ESPN via Leonard’s agent and multiple national outlets; the reported deal is two years, $115 million with a player option for 2028-29. Pablo Torre’s reporting is referenced as part of the commentary.