It’s the mark of a strong leader that your operation can run without you: that an identifiable culture is in place and those hired have enough responsibility that the enterprise isn’t dependent on one individual to navigate through the ebbs and flows and highs and lows. On that note, the Toronto Raptors announced Thursday afternoon that they had reached a multi-year contract extension with general manager Bobby Webster, who probably deserves a better billing than "Masai Ujiri’s right-hand man", and over time will surely get it. Webster was the charismatic Raptors president’s first hire when Ujiri was recruited from the Denver Nuggets in advance of the 2013-14 season. He was lifted from the NBA’s legal department where Webster vetted contracts and trades to make sure that they complied with league rules and the Collective Bargaining Agreement, a document he had helped craft. At 36, Webster is still one of the youngest general managers in all of sports but since he started with the NBA as a 20-year-old, he has 16 years of experience to draw on. His responsibilities and profile have steadily increased over his eight years in Toronto, with Webster moving up to the general manager’s role under Ujiri in 2017-18. They make a great team. Where Ujiri understands the benefit of engaging publicly and sharing grand ideas and broad visions, Webster is perfectly comfortable working behind the scenes and helping to keep those goals on track. Even before Webster took on a more public facing role, he was clearly someone Ujiri relied on. It wasn’t uncommon to ask a question about a nuance or detail about a trade or a signing and have the Raptors president laugh and say, “I’ll have to ask Bobby.” Where Ujiri at times brings the hammer, Webster favours a softer touch. When the Raptors made their franchise-defining trade for Kawhi Leonard in the summer of 2018, Ujiri pulled the trigger, but it was Webster who had laid the groundwork, working back channels to gauge the interest and requirements of the San Antonio Spurs. Increasingly it has been Webster who has been the point person for the team’s key player signings, be it Pascal Siakam last season or Fred VanVleet this past off-season. “He’s really good to deal with, he legitimately cares about the guys and their well-being and when we did the contract for Pascal we had a lot of one-on-one meetings with Bobby,” said Jaafar Choufani, part of the team at Life Sports Agency that represents Siakam, who signed a four-year deal for $130 million prior to his all-NBA season in 2019-20. “He’s been assigned a lot [by Ujiri] and been delegated a lot and he gets it done, without complaint and he does it with the interests of the franchise first and foremost.” This past off-season the Raptors' first priority was signing VanVleet to a new contract, and while it was Ujiri and Webster who travelled to Chicago the day after free agency opened to present the fifth-year guard with a four-year deal for $85 million, again much of the preliminary work had been handled by Webster, so when the time came there were no surprises, on either side. “I’m happy for Bobby,” said Brian Jungreis, who represents VanVleet. “He’s been a pleasure to work with professionally and to get to know as an individual. He’s always been approachable, honest, candid, genuine and easy to talk to on top of his basketball knowledge. “As an organization they have always stuck out in their approach and with Bobby continuing at the helm, I am sure they will have continued success.” The question, inevitably, is what role Webster will have for the remainder of his contract – the length of which was unspecified. Does his signing indicate that Ujiri – whose own contract is up after this season – has made sure all of his key lieutenants are taken care of before he reaches a new deal that will keep him in Toronto for the long haul? Or has the process of signing a still-young core, extending head coach Nick Nurse, taking care of the rest of the basketball operations and now Webster been about Ujiri doing some succession planning and making sure that the organization that has helped him reach great heights will remain in good hands when he leaves? It’s unknowable for the moment. In December I reported that there had been no meaningful conversations between Ujiri and Raptors ownership at that point, even though Maple Leaf Sports and Entertainment — owners of the NBA team as well as the Toronto Maple Leafs, Toronto FC and Scotiabank Arena, among other holdings — was ready to get a deal done whenever Ujiri wanted to talk. “I can promise you, it’s not [MLSE],” said a source with knowledge of the ownership’s thinking. “They’d have to be nuts not to [want to sign him]. It’s not like there’s a Plan A and a Plan B. There’s only Plan A, and it’s him. “But he’s a very deliberate guy, and the kind of guy you have to respect his space.” My understanding is that nothing has changed on that front and the ball is very much in Ujiri’s court when it comes to reaching a new deal with MLSE. At the very least, Webster’s signing – which has been all but done since before training camp opened – offers some measure of comfort in the event that Ujiri does move on after this season. With Webster’s deal not completed it would have been easy to get concerned that Ujiri was planning to airlift his hand-picked executive team to whatever new opportunity came along. That’s not on the table now. If Ujiri does find another opportunity he’ll be going alone and having to build an organization to match the one he’s be leaving behind, which is easier said than done, given the Raptors are fighting to make their eighth straight playoff appearance and have won 50 or more games for five years and counting, not to mention their title in 2019. If Ujiri’s next move does involve him leaving Toronto, he won’t have Webster to help move the chess pieces.
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