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Three key reasons Leonard was open to this deal to Toronto, according to sources: Familiarity with a Toronto organization that has the majority of its front office structure in place, now led by executive vice president Bobby Webster. Leonard also likes the city of Toronto and believes the Raptors can contend in the Eastern Conference.
Josh Lewenberg: Should also note, as I have before: in 13 years under this Masai Ujiri and now Bobby Webster-led front office, the Raptors have never moved multiple 1st-round picks in a trade. Don't expect them to do it for a 35-year-old Kawhi Leonard.
William Lou: “It's always been best-available, two-way players. That's always been our philosophy ... Sometimes you get into a trap if you try to take for fit in the first round." Bobby Webster on the Raptors drafting so many big two-way forwards
Josh Lewenberg: Notes from asst Raptors GM Dan Tolzman’s pre-draft avail: - Have done most of their workouts, digging in on prospects they like - No major differences in process under Bobby Webster - Draft considered wide open after top 10-12 - Keeping options open but cost to move up is high, happy at 19
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A little over a year ago, league sources say, Hawaii native Bobby Webster was quietly pursued by the University of Hawaii when the Rainbow Warriors needed a new athletic director. Webster, at the time, was still Toronto's No. 2 executive under Masai Ujiri. But there was no luring him away from the NBA or the Raptors — not even by the big school where he grew up — and that reality soon made perfect sense. One day after last June's draft, Toronto abruptly parted ways with Ujiri and would install Webster as his permanent successor some six weeks later.
Josh Lewenberg: Bobby Webster, via press release: "We're building something special here and I'm proud to continue to lead the Toronto Raptors as we work towards our next championship... This is a franchise that's focused on the future and we're ready for what's next."
Josh Lewenberg: MLSE CEO Keith Pelley: "Bobby (Webster) has an elite understanding of the game and the NBA and he's used that to build a team that competes at a high level... With Bobby and the Raptors, we've seen the results and we believe in where his leadership will take us."
Blake Murphy: The Raptors have extended Bobby Webster on a multi-year deal, and extended a handful of other front office members. Webster now also has an EVP title.
It’s expected that both general manager Bobby Webster and head coach Darko Rajakovic will be offered contract extensions in the coming weeks, Sportsnet has learned. Each of them have another year left on their current deal. As one well-placed source put it: “You don’t have your head coach and general manager head into the final year of their contracts as lame ducks, not after a playoff year.” As another said: “It will happen when it happens,” referring specifically to Webster, “but it will happen.”
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With Ujiri being introduced on Tuesday as president’s job with the Dallas Mavericks, the NBA gossip sphere was abuzz with how, when and with whom he would fill out his front office. At least one source speculated that he might try to hire Webster as his general manager in Dallas. Multiple sources I spoke with ruled that out almost instantly, on two grounds. One, now having had his own team to run, it’s unlikely stepping back to a supporting role would be something the current Raptors general manager would want to do, and two, the Raptors wouldn’t let Webster go. “He [Webster] is the captain of his own ship here,” said one source.
Omer Osman: Bobby Webster on Brandon Ingram’s fit in his first season with Toronto, and if he sees BI as a long-term fit with this group: “By all accounts, I think Brandon fit in, and I think now this is the time for him to continue to improve shooting, get bigger, get stronger.” “I think having two All-Stars in Scottie [Barnes] and Brandon was a great, great season.”
Josh Lewenberg: Bobby Webster on possibility of making a big trade this summer: "We're always going to be opportunistic in any trade market. It's the reason we've kept all our first-round picks. Financially we're well positioned... It would have to materially move us ahead from a contender standpoint"
Josh Lewenberg: Bobby Webster on the possibility of talking trade with Dallas (and his long-time boss Masai Ujiri) down the line: "It's funny when you have someone like that; he probably knows all the players we like and we know all the players he likes. So, sometimes it's hard to do deals."