It’s been a while since Kawhi Leonard won a playoff series—five years, to be precise. After leading the Raptors to their first championship in 2019, Leonard signed with the Clippers. He and his new team won their 2020 first-round series against the Mavericks, but lost to the Nuggets in the second round. A year later, they beat the Mavericks again, but lost to the Jazz in the second round after Leonard tore his ACL in Game 4.
That second first-round win against the Mavericks in 2021 was the last time Leonard won a playoff series. He missed the 2021-22 season, tore his meniscus two games into a first-round series against the Suns, which the Clippers lost, in 2023, suffered a first-round loss to the Mavericks in 2024 and one to the Nuggets in 2025, and missed the playoffs altogether this year after a play-in tournament loss to the Warriors.
Not winning a playoff series in five years isn’t a great look for an All-NBA-level player, and it heavily contributed to Bill Simmons questioning what the Raptors gave up for Leonard compared to what it took for the 76ers to get Jaylen Brown.
However, because of that trade, Leonard is in a great position to put an end to his string of postseason losses—and the Raptors need him to do just that. Otherwise, the trade will age badly.
If Leonard is healthy, the Raptors can be dangerous in the playoffs
The Raptors almost beat the Cavs in the first round without Immanuel Quickley and Brandon Ingram. Three of their leaders in minutes per game in the playoffs—Jamal Shead, Ja’Kobe Walter, and Collin Murray-Boyles— had never even been to the playoffs before, and Scottie Barnes had only seen four games of playoff action as a rookie before going into this series as the most important player on the team. And yet, they were just one win away from moving on to the second round.
With a veteran superstar in the mix and all of their most important players from the series still on the roster and more experienced, there’s no reason to believe that the Raptors can’t win a playoff series, especially if they’re good in the regular season and stay out of New York’s path for as long as possible.
A huge reason for Leonard’s disappointing playoff streak since 2019 has been his health, and it will also dictate his second stint with the Raptors. The franchise kept him healthy enough to lead the NBA in playoff minutes in 2019, and he played 65 games this past season. Both are good signs that he will be available enough for the Raptors to make a real difference, but it’s not guaranteed.
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