The Toronto Raptors have navigated a hectic and exhilarating offseason, but general manager Bobby Webster and the front office know that the job is far from finished. As the franchise looks to make a resounding leap into the upper tier of Eastern Conference contenders, the clock is ticking loudly.
With training camp looming in early September, the front office faces a critical window to finalize their roster architecture. Here are the three massive priorities the Raptors must resolve before the team hits the hardwood for the new season.
1. The Kawhi Leonard Trade Saga: Clarity is Crucial
Arguably the most pressing and anxiety-inducing subplot of the entire NBA offseason revolves around the stalled Kawhi Leonard trade and the ongoing league investigation concerning the Los Angeles Clippers and allegations of salary-cap circumvention.
The blockbuster agreement framework would see Kawhi Leonard make a sensational return to Toronto in exchange for a package featuring Gradey Dick, Brennan Ingram, and multiple first-round picks. However, the pending investigation has left the Raptors trapped in administrative limbo. Reports suggesting a resolution might stretch all the way to the brink of training camp threaten to throw Toronto’s seasonal preparation into chaos.
The Raptors cannot afford to linger in uncertainty, nor do they want to awkwardly bring traded players back into the fold if the trade hangs in the balance. In an ideal world, the league investigation wraps up immediately, the trade gets pushed through, and Toronto can secure Leonard on a fresh contract extension. Achieving total clarity will finally allow the front office to pivot and explore alternative avenues if necessary.
2. Finalizing the Two-Way Slots and 15-Man Roster Depth
With roster construction requiring meticulous balance, Toronto still needs to address the bottom of its depth chart, specifically sorting out its three available two-way contracts.
The battle for these developmental slots is heating up nicely. Standout candidates include Oregon center Nate Bittle and former 2023 second-round pick Seth Lundy, who lit up the Las Vegas Summer League as the team’s leading scorer. In fact, there is growing momentum behind the idea of retaining both players within the two-way framework.
Should the Leonard blockbuster finally cross the finish line, it could trigger a cascading effect on the main roster. Promoting a young talent like Chucky Hepburn or Jaden Bradley onto the active 15-man squad as the vital 14th player would simultaneously free up a two-way slot, ensuring Bittle and Lundy both get crucial developmental reps at the professional level throughout the year.
3. Securing Hometown Star RJ Barrett to a Long-Term Extension
While external acquisitions capture the headlines, internal security is just as vital. Forward RJ Barrett is officially entering the final year of his current deal and is tracking toward unrestricted free agency in 2027.
Following a gritty, impressive postseason series against the Cleveland Cavaliers, Barrett firmly established himself as an indispensable cornerstone and a long-term fixture of the Raptors’ competitive core. As one of the emotional heartbeats of the team, locking down the hometown hero to a lucrative contract extension is an absolute must.
Waiting only drives his price tag higher. Securing Barrett now gives the star forward the peace of mind to focus entirely on basketball—free from the looming distraction of contract uncertainty—while anchoring Toronto’s wing rotation for years to come.
As Bobby Webster and the Raptors front office race against the September deadline, solving these three massive puzzles will determine whether Toronto enters the new campaign fully prepared to conquer the East.
