‘Tis the season… for reuniting with exes?

The Toronto Raptors are reportedly in serious trade discussions to acquire Kawhi Leonard from the Los Angeles Clippers. The two-time Finals MVP departed Toronto in free agency in 2019 shortly after leading the Raptors to the franchise’s first NBA title.

Before you roll your eyes, these aren’t your run of the mill rumours to fill up airtime in the summer. ESPN’s Shams Charania and longtime NBA insider Marc Stein have both reported that the deal is at an advanced stage. With the former Finals MVP entering a contract year, Charania is also reporting that Leonard would only sign an extension with the Raptors if he were traded.

The Ringer’s Zach Lowe believes that the trade could be completed by Monday’s end. It just so happens to be Leonard’s 35th birthday.

The reported deal would send all-star Brandon Ingram, Gradey Dick, and some level of draft compensation for Leonard. After some initial worries that Leonard may just be using the Raptors as leverage to re-sign a deal with the Clippers, it appears that Los Angeles wants to trend in a younger direction and that doesn’t appeal to him.

Naturally, Raptors fans are losing their collective minds. There are a good chunk who feel this could take the team back into title contention while others see great risk and don’t want to entertain the idea of bringing him back at this late a stage in his career considering his injury history.

Kawhi Leonard made the All-NBA Second Team last season, averaging 27.9 points, 6.4 rebounds, 3.6 assists, and 1.9 steals. He shot 50.5 per cent from the field including 38.7 per cent from three, as well as 89.2 percent from the free-throw line. He played exactly 65 regular season games, the minimum required to be eligible for end of season awards.

He played 37 games in 2024-25 and 68 in ’23-24.

It should also be remembered that Leonard and the Clippers are still under investigation for possible cap circumvention, with Los Angeles reportedly paying him under the table to help sign him in free agency in 2019.

Leonard looked like one of the best players in the league again last season, finishing seventh in MVP voting. The potential of Leonard playing with Scottie Barnes is certainly tantalizing. So intriguing in fact, that even former Raptor Serge Ibaka couldn’t help but take notice of the rumours that are swirling.

Another point of concern has been offering Leonard an extension at age 35. The injury concerns are obvious, having to manage a chronic, degenerative knee condition. Raptors Vice President of Player Health and Performance Alex McKechnie was instrumental in introducing the NBA world to load management during the ’18-19 season, a concept that had Leonard sitting one end of back-to-backs and being very careful about the demands made of his body.

There were questions that arose regarding the process over the course of the regular season, but all was forgotten and forgiven when Leonard was healthy enough when it mattered most to lead the Raptors to a championship.

Leonard is owed $50.3 million next season and would be eligible to sign a maximum extension of approximately $125 million over two years and has reportedly been open to doing so with the Raptors.

The extension possibility has also been a sensitive subject in Raptor-land, as he could have it all in Toronto in 2019 but departed in free agency.