3. Bobby Webster, Toronto Raptors
Masai Ujiri is the name that gets all the credit for the Toronto Raptors‘ personnel moves, but he’s actually the team’s former general manager and current team president, so GM Bobby Webster is the one who’d be up for an award here. If the Kawhi Leonard trade goes as planned, more people will know his name.
That’s essentially what his candidacy hinges on. While re-signing Fred VanVleet and picking up Greg Monroe for frontcourt depth were solid moves, the make-or-break moment of the summer was the cold-hearted but cunning decision to trade DeMar DeRozan and Jakob Poeltl for a superstar that could be a one-year rental.
There’s no way of knowing what will happen in free agency next summer, especially for a 2018-19 regular season award, but if Leonard is healthy and the Raptors storm their way to a top-two seed as one of the favorites to succeed LeBron James’ reign in the East, Webster will be one of the top candidates for Executive of the Year.