One Offseason Decision the Raptors May Already be Regretting

The Toronto Raptors acquired Kawhi Leonard this offseason, but giving up multiple unprotected first-round picks could hurt them in the long run if their championship window closes quickly.

Feb 1, 2026; Phoenix, Arizona, USA; Los Angeles Clippers forward Kawhi Leonard (2) talks with NBA referee Scott Foster against the Phoenix Suns at Mortgage Matchup Center. Mandatory Credit: Mark J. Rebilas-Imagn Images | IMAGN IMAGES via Reuters Connect

The Toronto Raptors made one of the biggest moves of the NBA offseason when they brought Kawhi Leonard back to Toronto. Leonard undoubtedly makes the Raptors more competitive right now, as he brings extensive playoff experience and will play high-level basketball on both ends of the floor.

However, the price that Toronto ended up paying to acquire Leonard may haunt them in the long run.

The Raptors didn't simply add Leonard. They gave up Brandon Ingram, Gradey Dick, and two future unprotected first-round picks. That investment poses quite the risk when the return is an injury prone Leonard. For a team that is still trying to build around Scottie Barnes (Leonard won't be around forever), losing a significant amount of future flexibility is a large commitment.

Why the Trade Still Makes Sense for Toronto

Apr 26, 2026; Toronto, Ontario, CAN; Toronto Raptors forward Scottie Barnes (4) celebrates with forward RJ Barrett (9) after a win over the Cleveland Cavaliers in game four of the first round of the 2026 NBA Playoffs at Scotiabank Arena. Mandatory Credit: Dan Hamilton-Imagn Images | IMAGN IMAGES via Reuters Connect

It would not be fair to look at the trade exclusively from the perspective of what can go wrong.

Leonard's presence allows everyone else on the Raptors to grow into their roles. Barnes does not have to feel the weight of carrying Toronto on both ends of the floor. RJ Barrett and Immanuel Quickley don't have to feel the weight of carrying the offense when Barnes is facing a tougher matchup.

The Raptors added an established star who will completely change the way the team is defended. Everyone else will get easier matchups as a result of Leonard being on the floor. For a team like Toronto who believes that they are on the brink of being a contender in the Eastern Conference, making a blockbuster trade for an established star makes a lot of sense.

The Real Risk is What Happens After Leonard

Jan 14, 2026; Indianapolis, Indiana, USA; Toronto Raptors forward/guard Scottie Barnes (4) in the first half against the Indiana Pacers at Gainbridge Fieldhouse. Mandatory Credit: Trevor Ruszkowski-Imagn Images | IMAGN IMAGES via Reuters Connect

Due to Leonard's age, their championship window with him is relatively small. If the Raptors are able to become a contender in the next 2-3 years, then the draft picks that were sent off in the trade will essentially be a nonfactor.

But what happens if the Raptors remain a good team that can't quite make it over the hump?

That is where the decision to make this trade could come back to haunt Toronto. Unprotected first round picks can become extremely valuable if a team falls out of the playoff picture.

The picks the Raptors gave up are for 2031 and 2033, which is well after the Leonard era. There's no telling what this Raptors team will look like in five years, so while it is obviously too early to classify the Leonard trade as a mistake, it is certainly a gamble that may or may not pay off.

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