Skip to main content
All Raptors

The Most Important Trade in Toronto Raptors History

The Toronto Raptors proved how one trade can change everything and win a championship if the stars align.
San Antonio Spurs guard DeMar DeRozan controls a ball as Toronto Raptors forward Kawhi Leonard tries to defend.
San Antonio Spurs guard DeMar DeRozan controls a ball as Toronto Raptors forward Kawhi Leonard tries to defend. | USA TODAY Sports

It's been eight years since the Toronto Raptors made the biggest trade in franchise history, acquiring Kawhi Leonard in a blockbuster deal with the San Antonio Spurs.

In the full trade, the Raptors acquired Leonard and Danny Green in exchange for Jakob Poeltl, DeMar DeRozan and a 2019 first-round pick. The deal helped the Raptors win their only NBA championship less than a year later and it has also affected how the franchise does business to this day.

How the Kawhi Leonard Trade Impacted Raptors' Championship

The Raptors knew their championship window was running out, but they also needed a change after losing deep in the playoffs in 2016, 2017, and 2018. This prompted Masai Ujiri to make the tough decision to part ways with an All-Star in DeRozan and a 2016 first-round pick in Poeltl to acquire Leonard, who had just one year left on his contract.

It was a tough decision, but it was high risk and high reward, and it all paid off in the end. Leonard proved to be the exact upgrade the Raptors needed at the time, and they were able to utilize his skill set on both ends of the floor to create a team that was better built for the postseason.

That was extremely evident during the team's second-round series against the Philadelphia 76ers, when Leonard hit one of the most exhilarating game-winners in league history. It bounced off the rim multiple times before going down the bottom of the net.

Why a Kawhi Leonard Reunion Makes Sense for Raptors

A big reason why the trade was controversial was that Leonard was unwilling to sign a long-term extension with the Raptors. Toronto took the chance anyway, and it paid off as they won the championship. They lost Leonard in free agency to the hometown Los Angeles Clippers, where he had always wanted to play.

After seven years with the Clippers, Leonard is looking to move on once again. He has one year left on his deal, and he's only willing to sign an extension in one place: Toronto. That wouldn't have been possible without his championship run in 2019, and now Toronto might be able to parlay that success eight years later.

On June 30, the Raptors agreed to a trade with the Clippers that would have sent Brandon Ingram, Gradey Dick and multiple first-round picks to Los Angeles, but the deal has been paused until the investigation regarding the Clippers' alleged salary cap circumvention is complete.

Leonard's defence would mesh well with Scottie Barnes and Collin Murray-Boyles, and he could take some of the pressure off of creating on offence from Immanuel Quickley and RJ Barrett.

Very few teams get the opportunity to win multiple championships in different eras off of one trade, but this could be possible if Toronto hoists the Larry O'Brien Trophy once again with Leonard as the catalyst.

Sign up for our free newsletter, which will bring all Toronto Raptors On SI stories every weekday to your email.

Add us as a preferred source on Google

Loading recommendations... Please wait while we load personalized content recommendations


Published
Jeremy Brener
JEREMY BRENER

Jeremy Brener is the publisher for Toronto Raptors On SI. He has been with the website since October 2025. He has appeared on the "Basketball North" podcast and TSN 1050 talking about the Raptors. He graduated from the University of Central Florida with a Bachelor's degree in Broadcast Journalism minoring in Sport Business Management. Brener can be followed on Twitter @JeremyBrener.

Share on XFollow JeremyBrener