The Toronto Raptors are among the winners of the ongoing 2026 NBA offseason, which has been dizzying with all the trades and free agent signings.
Earlier this offseason, Toronto executed a blockbuster deal to bring back one of the greatest players in Raptors history — who also played just one season with the franchise.
Seven years after leading the Raptors to their first ever NBA championship, Leonard is back in Canada ready to lift Toronto back to title contender status. With the nostalgia already overflowing, many fans are calling for another reunion. Why not also bring back Leonard’s predecessor, DeMar DeRozan?
Raptors to Reunite With DeMar DeRozan? A Team Icon Says the Star Free Agent Can Still Make an Impact
GettyKyle Lowry #7 and DeMar DeRozan #10 of the Toronto Raptors during the second half of Game 4 of the second round of the Eastern Conference playoffs against the Cleveland Cavaliers at Quicken Loans Arena on May 7, 2018.
On the topic of reunions, another one happened after Leonard was brought back in a trade. Ex-fan favorite point guard Kyle Lowry signed a one-day contract with the team to retire as a Raptor. While Lowry believes his buddy DeRozan isn’t far from retiring himself, the former six-time All-Star believes DeRozan has plenty of basketball left in the tank.
“He’s getting close (to retirement) but he still has a lot of basketball left in him,” Lowry said, according to Raptors insider Michael Grange.
DeRozan, who turns 37 next month, was the face of the Raptors for nine seasons before an acriminous split. After the 2017-18 season — where the Raptors were swept out of the playoffs by LeBron James and the Cleveland Cavaliers — DeRozan was traded to the San Antonio Spurs in exchange for Kawhi Leonard and Jakob Poeltl.
A four-time All-Star in Toronto, DeRozan was stung by the trade — as were Raptors fans, who embraced DeRozan unlike any franchise star in the past because of his willingness to commit to Toronto.
Although it has been eight years since DeRozan was traded, has he let go of the past enough to come back to Toronto? Recent rumblings suggest DeRozan — who is now a free agent after being waived by the Sacramento Kings — would be open to a reunion.
The DeRozan-Lowry Era Fell Short, But One Reached the Mountaintop
GettyKyle Lowry delights during the Toronto Raptors’ 2019 NBA championship parade.
For years, the DeRozan and Lowry led Raptors were among the top teams in the Eastern Conference. The only hump they couldn’t get over was James.
The 2017-18 season felt like it was finally Toronto’s turn to snatch the Eastern Conference crown. After all, the Raptors finished with the top record in the conference with 59 wins, while the rival Cavs had lost Kyrie Irving, their second best player, in the previous offseason.
Instead, the DeRozan era hit a new low. The Raptors were swept. The head coach was fired. DeRozan was gone.
But Lowry stayed. And he received a new running mate.
Just one season later, Lowry cemented himself as an all time great Raptor after winning the 2019 NBA championship behind the brilliance of Leonard, who won Finals MVP for the second time in his career.
Lowry won it all. DeRozan, meanwhile, could only sit back and watch his bestie do it without him.
How fitting would it be if DeRozan, who was traded for Leonard, joined Leonard in Toronto next season while Lowry looks on as a supporter?
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