Kawhi Leonard spent only one season of his 14-year NBA career with the Toronto Raptors and he made it count.

Leonard led the Raptors to their first NBA championship in franchise history, while securing the second Finals MVP award of his career. That led to his first contract with the Los Angeles Clippers, which was a three-year, $103.1 million deal.

Since then Leonard has signed two contract extensions with the Clippers, the first in 2021 after he declined his player option for that season and then re-signed with the team on a four-year, $176.3 million max extension.

The latest contract extension came in 2024, where Leonard signed a three-year, $152.4 million deal that kept the two-time Finals MVP in Los Angeles through the 2026-27 season.

However, there are rumblings about Leonard’s availability on the trade block this year.

The Raptors are interested in reuniting with the small forward and Leonard is reportedly open to signing an extension with Toronto, per NBA insider Jake Fischer.

While Kawhi Leonard’s preference is to remain with the Clippers, league sources say the two-time Finals MVP would be open to signing an extension with Toronto, amid the Raptors’ own interest in reuniting with Leonard.

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— Jake Fischer (@JakeLFischer) June 25, 2026

The Detroit Pistons and Miami Heat have also been linked to Leonard, but the 34-year-old wouldn’t have interest in inking an extension with either team.

Perhaps Leonard is also nostalgic about his former teams as he is reportedly only considering signing an extension with either Toronto or the San Antonio Spurs.

Ultimately, a reunion scenario would only transpire if the Clippers made Leonard available on the trade block. Currently, the team believes they “still have avenues to fortify their roster around Leonard and remain in Western Conference contention,” according to Fischer.