Why Kawhi Leonard should have stayed with the Raptors

Leonard’s tenure as a Clipper has certainly not gone according to plan, and it makes you wonder whether the six-time NBA All-Star made the wrong decision in 2019. 

Despite spending just one year with the Toronto Raptors back in 2018-19, it felt like the perfect fit, and the Klaw might have made a mistake bolting so quickly. 

It may be revisionist history to look back on his decision, but now feels like the appropriate time to do just that. Here's two reasons why Leonard should have stayed in Toronto.

Championship roster

First off, the team had just won the championship; what else can you want? Led by Leonard, the Raptors brought the Larry O’Brien Trophy to Toronto, and Canada, for the first time ever. It was a special season with a great team, full of depth from top to bottom. Forward Pascal Siakam, guard Fred VanVleet, forward OG Anunoby and forward Norman Powell were all just entering their primes, while veteran point guard Kyle Lowry still had multiple elite years left in him. 

It fit perfectly around Leonard, and the roster was built to continue competing for titles had he stuck around. The Eastern Conference was wide open for the taking for years after LeBron James went to the Los Angeles Lakers in 2018, a big reason why Toronto won the East in 2019, and it should have been the Raptors seizing full control of it moving forward. 

Health and medical staff

Injuries have overshadowed a lot of Leonard's career, and he's struggled mightily to stay healthy since leaving Toronto, playing more than 57 games just once in five seasons as a Clipper (68 games in 2023-24). Even while missing a lot of regular-season action, his body has often worn down come the playoffs, forcing him out of action at the most critical time of the year. 

Leonard was load-managed throughout the 2018-19 regular season with the Raptors, playing in 60 games, and that strategy appeared to work best for him. He managed to play in all 24 postseason games averaging 30.5 points per game en route to an NBA title and Finals MVP. He formed a trust with the medical staff in Toronto, something he’s had difficulty finding anywhere else. 

We'll never know how things would have played out if Leonard had re-signed with the Raptors in 2019, but what's certain is that it couldn't have gone any worse than the debacle that's been his time with the Clippers.