Iolani grad remains among youngest, but experienced NBA executives

HONOLULU (HawaiiNewsNow) – We are just a few weeks in to the 2024 NBA Season, which means it’s primetime for Bobby Webster.
The Kailua native is now entering his seventh season as general manager of the Toronto Raptors.
At 40 years old, he’s among the youngest in his position, but has the wisdom of a veteran executive.
“There’s different experiences like going to all-star games and being in the NBA Finals and sitting there for a playoff game,” Webster said.
“From a scouting perspective, I get to go to March Madness and watch those games, there’s a little bit of the fan in me, that still appreciates just going to watch basketball and trying to find that next talent.”
Scouting future stars is only one aspect of the job.
Webster joined Toronto in 2013 after previously spending seven years working for the league office in New York.
When the Raptors won the NBA Championship in 2019, that was only his third season as the team’s GM.
Webster knows full well team success goes well beyond whatever happens on the court.
“You have coaches, you have a medical department, you have operations staff, so just keeping that unit combined,” Webster said.
“There’s a lot of outside noise too with social media, so sort of creating an environment for the players where they feel supported but also pushed. All of that, as much as I enjoy the basketball, that probably takes up more of my time sort of managing people.”
Over the last decade, he’s become one of the most respected executives in the association through a leadership style rooted in his local upbringing.
“A lot of it is a byproduct of where you are from, so growing up in Hawaii, I think there’s a lot of different cultures,” Webster explained.
“You grow up sort of as a melting pot and i think that’s taken me far in life — understanding people come from different backgrounds, understanding people have different life experiences. Also, growing up playing basketball and being in basketball culture has helped me.”
While he’s based 4,600 miles away from the islands, Webster flies back home as often as he can. He even helped bring the Raptors to Oahu for training camp in 2017.
Since then, the team has been pushing for a return trip.
“I’d say our staff more than anyone is like ‘Bobby when we going back to Hawaii?’” Webster said. “We are a team in Canada, so I have to be a little bit mindful of where we go. It’s always top of mind for us, and we’d love to get back.”
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