Multiple titles for the Raptors? There’s no quit in GM Bobby Webster’s dictionary


It’s not a corner office in the truest sense of the corporate meaning, and it’s not really all that spacious, and it isn’t chock full of mementoes and brimming with autographed pictures of this star or that star or some important politician or what have you.

It’s nestled among a row of similar spaces alongside the two practice courts at the OVO Athletic Centre, home of the NBA champion Toronto Raptors, a kind of self-effacing space that’s really comfortable but not in the least boastful.

It’s actually kind of perfect for its inhabitant.

Bobby Webster — the team’s general manager, the right-hand man in the background behind the globally famous Masai Ujiri, one of the relatively anonymous players in a highly competitive game dominated by type-A personalities — sits behind his desk, comfortably chatting and explaining that the fame, the adulation, the public glory is the least of his concerns.

He’s done what few men in his position have ever done, and he could rightfully squawk about it or boast about it — or be satisfied with it and play the “we’ve got a chip on our shoulder” card — but that’s the last thing he’d do.

“The people that I work with every day — ownership, the players — that’s who really matters,” Webster said in a rare sitdown interview this past week. “At the end of the day, I’m not necessarily in it (for glory). As long as our little family knows, that’s fine.

“If I felt like the people around here didn’t care, then you’d have to look at it a bit more, but I genuinely feel that here.”

In many ways, Webster is the perfect colleague for Ujiri. He was the first front-office type hired by Ujiri after he came back from the Denver Nuggets, and they’ve been together for seven seasons. While Ujiri has become this important global figure, he’s done it because he knows he can trust Webster to handle every aspect of running the organization.


That’s all that matters to each of them.

“I think the interaction has always been constant: This is who Masai is, this is what he is,” Webster said. “Maybe it’s changed incrementally over the years, but we know the other commitments that he has and that’s why we’re here.”

Make no mistake, though. There burns in the boyish 35-year-old from Hawaii a competitiveness and intensity that matches his more verbal, demonstrative boss.

Webster isn’t going to stand on a stage in front of thousands of screaming fans and say “Eff Brooklyn” — as Ujiri did before Game 1 of a playoff series against the Nets in 2014 — but he’s going to think it and feel it and want nothing more than to beat the Nets, the Warriors, the Sixers, the Bucks, the Rockets.

He’s going to want all of that intensely. It’s what drives him.


“The goal has always been to win a championship,” he said. “You can go back and talk to 21-year-old Bobby and that’s why I decided to do this: to win a championship.”

Or two. Or three. Or to eventually join the pantheon of all the greats.

“Obviously you get into this business to win one and … if you want to be kind of legendary you want to win multiple (titles), so that’s the fun of this challenge. How do you get this group to win, and which parts of this group are going to be part of the next Raptors championship?”

Legendary? Seems like an odd and uncharacteristically bold word for him to use.

”I just think if you look back, I don’t think every franchise has won one. I bet half of that (group) hasn’t won two, so now you’re starting to get into a different (historic) group.”

That’s why this season holds such intrigue for Webster. It would have been easy — and much better, truth be told — if the Raptors had convinced Kawhi Leonard and Danny Green to stick around. Running it back, as the cliché goes, is so much easier when all pieces are familiar and in place.

But that’s not really fun, is it? It’s more fun to build and tinker and deal with a different reality and figure things out.

“The fun of it is exactly what we have here,” he said. “It’s unknown. You don’t know how everything is going to play out and that’s the fun of it, and I’m sure by January or February we’ll be in it deep again and be evaluating the team: Are we missing something?

“In some ways, if everyone comes back we know exactly how the season is going to go. That’s part of the fun for us. You see other teams unfold. We really don’t know how it’s going to unfold, who’s going to start … who’s going to be on the second unit, who’s going to be on the team.”

That drive to find those bits — the starters and the backups and the necessary personalities for the living thing that is a team — is Webster’s ultimate pursuit. And no one should wonder about his competitive intensity and the sense of satisfaction he feels when it all comes together.

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“This is one of the few (professions) where you can say, this industry is designed around winning this.

“Everyone can do it in their own way and everyone has different techniques and we all kind of have generally the same rules to play by. It’s set up perfectly for someone who is competitive or driven to say: I’m going to try to do this better than you.

“That’s the thing.”

Doug Smith