The Toronto Raptors have a pair of very impressive men running the team. Their general manager, Bobby Webster deserves a shot to be a solo head executive in the NBA.
Although often misrepresented, Bobby Webster is the General Manager of the Toronto Raptors, not Masai Ujiri. Ujiri, who is the President of Basketball Operations, decided to bring Webster onboard as his first executive hire with the team.
Webster started with the Raptors in 2013 as Vice President of Basketball Management and Strategy before working his way up to be Assistant General Manager. In June of 2017, Webster was promoted yet again to his current role, as General Manager. It’s only a matter of time before he is the highest-ranking executive in an organization, even if that is not in Toronto.
When Webster took the role of GM, he became the NBA’s youngest ever to occupy the position. At the time, the Head Coach, Dwane Casey, spoke glowingly about his then 32-year-old boss.
"“He’s a breath of fresh air. He’s smart. He’s energetic. He’s always around. He knows the [salary] cap inside out so he’s a huge addition to our organization. Someday he’s going to be a general manager-president in this league. I know Masai Ujiri is going to hate to lose him, but that day is coming. He’s good at what he does. I told him I’m jealous, I don’t know why he would move to Toronto and leave this. But he’s a great addition and he’s a bright star in the NBA.”"
Casey was likely right about Webster’s future. He was a good hire with a strong background rooted in knowledge on the salary cap. Having worked for the NBA’s head office for seven years and finishing there as associate director for salary cap management, he was well versed in the business of basketball.
Though young, Webster’s experience is vast. He was part of the league’s Labor Relations Committee and was involved in contract negotiations with the players union. He has also worked for one of the brightest minds in the sport, Ujiri. Now, Webster can also boast that he is a title-winning general manager.
ESPN Sources: The Washington Wizards are preparing to make a prolific offer to Toronto's championship architect Masai Ujiri -- as much as $10M annually -- to run its basketball operations. https://t.co/KQf18YUkLN
— Adrian Wojnarowski (@wojespn) June 14, 2019
Shortly after the Raptors won the Larry O’Brien Championship Trophy, it was reported that the Washington Wizards were interested in poaching Ujiri and were willing to pay him up to ten million dollars a year. While that turned out to be false, they perhaps should have been looking at Webster to run their team.
The difficulty for any organization interested in Webster is to know which decisions originated with whom. Did Webster mastermind important team transactions or were they Ujiri’s moves?
It was Ujiri who told the media that the Raptors needed a “Culture Reset” at his end of the year press conference two seasons ago. It was Ujiri who was credited by the media for firing Casey and replacing him with Nick Nurse. And it was Ujiri who Kyle Lowry felt had betrayed him when the Raps traded away his buddy DeMar DeRozan for Kawhi Leonard.
In actuality, both Ujiri and Webster worked in tandem. Webster’s long-term relationship with Brian Wright, the San Antonio Spurs assistant general manager, played a significant role. Knowing each other since they were both interns with the Orlando Magic, they were able to help make headway on the deal.
It’s time for a team to take a chance on Webster and letting him run their organization without a Ujiri safety net. So long as there is a President above him with the Raptors, he will never be given full credit for any moves he makes. A change of scenery would help Webster establish his own value.
Toronto fans will want to keep Webster for as long as possible. However, in the high-stakes landscape of NBA front offices, executives are always looking for the next step.
That’s not to say that leaving Toronto is necessarily right decision for Webster. There is no reason to believe that he isn’t happy with the organization, and the front office has clearly been effective since he’s been there. He just happens to be ready to run a team with just ownership to answer to.
The timing is right for Webster to be further empowered. Whenever he wants to make the leap, there’s a good chance he will excel wherever he is.