Does Bobby Webster have another trick up his sleeve?

How does the guru continue to build given the salary restriction? Does he have any other tricks up his sleeve? Or at least a plan? While the Raptors are closer to winning a championship than they were three months ago, they’re certainly not the favourites. Can a team with an Immanuel Quickley-RJ Barrett backcourt win a title? Can Jakob Poeltl get healthy enough that he’s at least a viable option? What happens if Ja’Kobe Walter, Jamal Shead, or Collin Murray-Boyles don’t take a step forward like many expect? Mamukelashvili was a big injection of offense off the bench, how can that be replicated? There are still lots of questions left to be answered. Not to mention, Barrett is an unrestricted free agent at the end of the season while Shead and Jamison Battle are hitting restricted free agency. Does it make sense to extend Barrett? Or will he be shopped at the deadline? The Raptors have been long connected to Domantas Sabonis, maybe Barrett is traded to Sacramento? The answers to these questions will define the Raptors season.

Last time Leonard was a Raptor, Toronto made a secondary trade at the deadline to acquire Marc Gasol. It was an underrated move at the time that completed the puzzle, vaulting the Raptors to true championship contention. Gasol was the perfect fit as a spacing, defensive, playmaking center. Which is, ironically, exactly what this version of the team needs. If you could plop Gasol on this squad… Whew. Maybe Webster can convince him to unretire?

The issues imposed by the first apron, and the fact that the Raptors have so much money tied up in either net neutral, or negative assets, make pulling off any deal to improve the team much more difficult. The Raptors do still own their own first round picks in 2028, 2029, 2030 and have a swap with the Clippers in 2027. Of those picks the Raptors can only really trade their 2029 pick due to the Stepien Rule, but maybe that’s enough to entice a team to part ways with a more valuable piece?

Who that may be? I don’t know. There aren’t many players out there that fit what the Raptors need. Whether that’s a center or a guard, I just don’t yet know what makes sense. It’s why I don’t think anything will happen until the trade deadline at the earliest. No point in rushing it until you see what you’ve got.

That’s been Webster’s MO, and I don’t expect it to change. He’s always been particularly disciplined when it comes to his deal-making, not often trading multiple picks and usually evaluating every option for as long as he can before making a decision. His calculated ways of doing business have been successful to this point, and while Leonard’s extension has opened the contention window a bit longer, he doesn’t have much time to waste, and every move needs an extra level of precision.

At this point, Webster has one move that he executes really well, and that’s trading for Kawhi Leonard. In both scenarios (whether he orchestrated the original deal or not), the Raptors bought low on a superstar. In pushing up the timeline, he can’t afford to wait for another opportunity like that to present itself, he’ll have to create his opportunity this time around to propel the team to the next level. Is he up to the task? TIme will tell.