The superfluous nature of modern society often lends itself to quick fixes. A pair of clothing rips? Throw it out. Kitchen appliance breaks? Probably best to get a new one. Ever forget your reusable grocery bags at home? Well, there’s no turning back now and you’re going to be adding a couple more to that stash in the closet.
There are times where replacing something is probably for the best (one more trip on the 401 in my old Hyundai could very well have been my last). But there’s also something to be said for sticking with things, with people. For what we learn along the way by fixing things, the resiliency we develop, the deep insight into the specifics of how something works – be it managing with iffy brake lines or running the Toronto Raptors.
That’s one reason why the Raptors extending Bobby Webster and giving him the “head of basketball operations” title is a good thing. Continuity is often a competitive advantage for organizations, be it in pro sports or elsewhere.
Another is that he’s smart, well spoken, driven – good at what he does. Webster spent time with the NBA’s front office in his 20s, advising all 30 NBA teams on the CBA, salary cap, and luxury tax. But that’s already well established. It was well established that Masai Ujiri was good at the job too, and it didn’t keep him here.
So why keep and promote Webster? Isn’t there some other newer, shinier executive who could swoop in with the perfect formula to bring the Raptors back to the top?
Well, no. There isn’t. As our Samson Folk once said: “Team building in the NBA is a difficult, nebulous beast of a job.” The feedback on decisions is delayed; there is no set procedure that guarantees success. Yet, in a realm where so little is within a team’s direct control, continuity among leadership can be a differentiator.
The Oklahoma City Thunder stuck with Sam Presti’s measured approach through thick and thin and look where it got them. Brad Stevens was in the Boston Celtics organization for over a decade before their 2024 championship, only replacing Danny Ainge after he retired from the general manager role. And the list goes on: Calvin Booth was just let go, but he spent six years with the Denver Nuggets prior to their recent championship, Jon Horst’s 13 years with the Milwaukee Bucks prior to them winning in 2021, Bob Myers leading the Warriors to greatness.
On the other hand, many teams that have turned over their front office leadership in recent years are in undesirable positions. The New Orleans Pelicans (Bryson Graham), Charlotte Hornets (Jeff Peterson), Phoenix Suns (Brian Gregory) and Sacramento Kings (Scott Perry).
Sure, it’s not like just keeping the same people involved in the decision making will guarantee good results eventually. They need to make good decisions. And the Raptors’ front office, including Webster, has done that in recent years.
After a stretch where the Raptors had few draft picks and missed on the ones they did, the selections of Gradey Dick, Ja’Kobe Walter, Jonathan Mogbo, Jamal Shead and Ulrich Chomche all appear promising. Collin-Murray Boyles could soon join Dick as another late-lottery success.
While it has polarized some, the acquisition of Brandon Ingram did undoubtedly bring in surplus value and immense talent. At best he helps rearrange the Raptors’ offensive hierarchy into functionality. At worst they have him and other players they can pivot off. Acquiring and then dealing Davion Mitchell was a tidy piece of business.
Who to directly credit for these moves is unclear, often it isn’t one person but rather a collective process. What is certain is that Webster was a part of the decision-making group that made these choices. Just as he was part of the process in the past when the Raptors front office made savvy deals on their way to a championship.
Webster is the fifth longest-tenured general manager in the league, trailing only Presti, Andy Elisburg, Sean Marks and Rob Pelinka. MLSE’s decision to elevate him to the Raptors’ head leadership role is in part a bet that this experience matters.
A new purchase is exciting in its novelty, but that eventually wears off. A good leather jacket or kettle smoker gains character over time, through the process, distinguishing it from its peers. Webster has longstanding relationships with Toronto’s players and staff. He has grown and learned over time what it takes to be not just a successful NBA executive, but a successful NBA executive in Toronto. And that familiarity is invaluable.
