In 2018, the Toronto Raptors pulled off one of the most game-changing trades in NBA history when they acquired Kawhi Leonard from the San Antonio Spurs. Although Leonard played only one season in Toronto, he led the Raptors to their first NBA championship during the 2018-19 season.
Looking back, Raptors general manager Bobby Webster recalled how Toronto beat everybody else and got Kawhi. In an interview on the “Hello and Welcome” podcast, Webster revealed that his relationship with then Spurs assistant general manager Brian Wright was the key to winning the Klaw sweepstakes.
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“I always tell young people when you’re coming up, it’s like ‘Hang with your crew.’ Like, stop trying to get the attention of everyone who’s older than you and the elder ones, because like you and your crew are going to be the ones that sort of rise in power and become and don’t always sort of seek the approval of everyone above you. Like you create your group and go,” he said.
Webster and Wright once worked together
Many people credit former Raptors President Masai Ujiri for bringing Kawhi up North, but it was actually Webster who was key in that deal. Before arriving in Toronto, Webster was an intern with the Orlando Magic and Wright. Although they ultimately went their separate ways, they kept their friendship and unbelievably, that was what put the Raptors among the favorites to land Leonard.
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“I think the deal happened July 17th but I always think back, we were in Vegas for a draft workout and Brian was there and I was kind of sitting back, like standing back off the court and Brian does this like little back like a moonwalk to me, and he’s like, ‘Hey, like are you guys interested?’ And I remember that was the first thing where like he approached us,” Webster added.
After that initial conversation, the teams spent the next two months trying to discuss a trade. With Toronto having a lot of desirable pieces back then, different iterations of the deal were discussed, but there was no agreement yet. And then came Wright’s surprise revelation to his good buddy when they met again during the 2018 Summer League.
“Brian grabs me at Summer League, and I think it’s one of those where you said like you don’t know how close you are to the negotiations. I think he put it to me, Brian. I was like, ‘Is this real? Like, are you guys really considering this?’ And he was like, ‘Bob, the deal is at the two-yard line. ‘ I was like, ‘Oh, we’re like there?’ He goes like, ‘Yeah,’ so then you get that sense too,” he continued.
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It reminds us of the Luka trade
It’s unclear when Wright and Webster talked in Vegas. However, the 2018 Summer League began on July 6th, 2018, and the Leonard trade was finalized less than two weeks later. Although there was a one-year period when Kawhi trade rumors floated around, and the Klaw made it known that he wanted to play close to home in Los Angeles with the Lakers, how Toronto became a destination and how the two teams moved about with the deal reminds us of how Nico Harrison and Rob Pelinka swapped Luka Doncic and Anthony Davis.
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Harrison and Pelinka have known each other for decades. Nico was Kobe Bryant’s Nike rep, while Pelinka was KB’s former agent. They admitted to having conversations about trading Luka out of the blue as friends first, then GMs, and until it became a real thing. Nico wanted a specific player from the Lakers — Anthony Davis — and the deal was done without a hitch or anybody knowing about it. Meanwhile, Wright wanted DeMar DeRozan for Kawhi, and he got that through his former Magic officemate.
Many criticized Nico and Rob for conniving to gift Luka to the Lakers, but after hearing Webster’s Kawhi story, it’s clear that the Luka-AD trade wasn’t the first of its kind. And it’s a common practice among executives to talk to their friends first before talking to everybody else.
As Webster said, relationships with your peers are important, and his connection to Wright made the difference. Maybe Masai did the heavy lifting for Toronto, but without the former Magic interns, there might not be a championship banner today at Scotiabank Arena.
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This story was originally reported by Basketball Network on Aug 25, 2025, where it first appeared in the Latest News section. Add Basketball Network as a Preferred Source by clicking here.