Photographer: Leah Friel, Wardrobe Stylist: Kim Smith, Makeup + Hair: Risa Hoshino, On Location: TBD Hawaii at Lotus Honolulu Hotel

Most might view local boy Bobby Webster’s rise to General Manager of the reigning NBA Champions — the Toronto Raptors — as a dream come true, a passion finally fulfilled. The actual story, though, is much simpler than that. Webster, 35, got his proverbial foot in the door with no fanfare and no clear-cut avenue to the world of professional sports.

“People won’t believe it … but I found a job online and applied for it,” he recalls. Thanks to a studious steadfastness while attending University of California, Santa Barbara—where he graduated in three years with a degree in economics—Webster was able to spend his would-be senior year investing in internships. This trek led him to Washington, D.C., where, thanks to his sports network-employed roommate, he was able to attend a handful of Washington Wizards games—for free.

“I asked him, ‘How’d you get this job?” Webster recalls. “He said, ‘Oh, I applied online.’”

So apply Webster did. He journeyed from the northern East Coast to Florida, landing himself an entry-level gig with the Orlando Magic in his early 20s.

“I didn’t even know jobs like this existed,” he says. “When you growing up playing sports, you want to be a professional player or a coach.

“But it’s never, ‘Oh I want to be a general manager,” he adds with a laugh.

Indeed, Webster grew up playing the sport he’s devoted much of his career to: He’s an ‘Iolani standout, who won a state championship during his senior season. His acumen for critical thinking, paired with his love and knowledge of the game quickly became evident, and in the mid-2000s, the Kailua native found himself in New York (where he met and married entrepreneur Lauren Schwab, cofounder of Negative underwear) heading up the NBA’s salary cap management team as associate director.

His journey, though, was not yet over. In fact, it was just beginning. Webster’s hard work and keen mind for the biz allowed him another chance to move within the NBA sphere, and he once again found himself considering a move, this time out of country up to Canada to join the Toronto Raptors team. Brought on by president Masai Ujiri, Webster first held gigs as vice president of basketball management and strategy, and then assistant general manager, before eventually heading operations as the NBA’s youngest GM in history in 2017.

His appointment came at the tail end of the illustrious season that saw the Golden State Warriors win the NBA championship. In his first full-fledged season as GM, Webster and the Raptors once again saw Golden State win the top title. But all that was about to change in Webster’s second season as general manager, much to the Warriors’ chagrin.

In headlines that rang around the world, the Toronto Raptors ended Golden State’s bid for a three-peat and brought to Canada the franchise’s first-ever NBA championship earlier this year. Not bad for a second-year GM.

But what does the illustrious title of general manager mean?

“I just generally manage things,” Webster says with a hearty laugh. But in all seriousness, there’s a lot that goes into the gig, from the day-to-day operations, to assembling the team and coaching staff, and managing the medical team, front office and scouts. The fun of it, though, is all the basketball parts, to hear Webster tell it.

“It’s finding the players, and either trading them or drafting them or signing them,” he continues. “It’s seeing it all come together. As the front office, we put all the structures in place for the players and coaches to succeed.”

As GM, Webster has the unique ability and privilege to problem-solve what the other 29 teams in the league are trying to figure out: How to win an NBA championship.

“You have to think about issues from every angle and how to problem-solve,” he says. “That’s not unique to basketball or the NBA or winning a championship. But it is being dynamic and thinking about the issues as critically as you can. I’m just applying that to the world of professional sports, which is its own little small sliver of society.”

Webster’s path was and remains totally uncharted.

“In a lot of ways, there’s no one for me to necessarily follow,” he says.

There’s an infinite number of ways to assemble a team, its coaches and affiliate staff. There are also a number of ways to win a championship, but it’s those variations that make the game really beautiful.

And what makes or breaks those adaptations is the work Webster does behind the scenes.

“For however many years, there were coaches and players,” Webster explains. “For [the coach], all you’re thinking about is how you’re going to win the next game.

But, with the rise of any industry or professional sport, the NBA changed. Coaches, whose attention is and should be on court play, cannot then travel the world to find new talent to add to their ranks. What was required to win championships quickly grew to outside of the coaches’ scope of responsibilities.

That’s where people like Webster come in.

“It became, ‘OK, coach, you coach. Players, you play. We’ll do everything else,” he says. “We have players from Cameroon, Congo and Spain. We have to go out and find those players. We go watch them when they’re younger.

“We’re competing against the other teams that want to do it in their own different way with their own set of people,” Webster adds. “And you never really know what will work until you, obviously, win a championship and you realize, ‘OK, that worked.’”

This past season, work it did. The Raptors—led by the soft-spoken Kawhi Leonard (who since has moved to Los Angeles to join the Clippers), guards Kyle Lowry and Fred VanVleet—beat Golden State in six.

“We won the championship,” Webster reiterates. “That’s a standard that now exists for the Raptors. Now, whether it’s new players or existing players, we’ll be able to hold them to that standard, and we’ll be able to hold ourselves to it for the future.”

With a win under his belt and a young family to attend to, the Raptors’ GM spent the summer months enjoying a little R&R in his hometown of Kailua—an oasis for the ever-busy NBA exec. It’s a time for him to trade in the suits and dress shoes for board shorts and bare feet, and, really, he wouldn’t have it any other way.

“Coming home, going to the beach, going on hikes; it reminds me of a slower pace, a different perspective,” he adds. “I use this time to re-energize a little bit and slow things down.”

He and his family—made up of wife Lauren, 2-year-old son August and a nearly 1-year-old Wailea—trekked around O‘ahu, making stops at all-time- fave Helena’s Hawaiian Food, among others. But nothing, Webster says, beats his mom’s home cooking.

“We eat a ton of poke and Hawaiian food,” he says. “Where we can get it … we get our fill here.”

And, he says, Toronto is not much different than Hawai‘i in terms of ambiance and that melting-pot blend of cultures. In fact, BBC named Toronto the most diverse city in the world, which is something he’s quite accustomed to, having grown up in the islands.

In fact, being within the NBA sphere isn’t much different than, say, ‘Iolani playing Punahou. Just, on a grander scale.

Practices are still grueling and tough on the body. Drills remain repetitive, yet necessary. Halftime in the locker room continues to be filled with emotional pep talks. Every player still has his own way of preparing his mind before a game.

“Except you jump on a private plane to get there,” Webster adds with a laugh. “Every game is on national TV, every game is written about a hundred times to say what you did right or what you did wrong. Everything is super magnified [in the NBA]. But at its most basic level, it’s the same.”

The binary (and, quite honestly, awesome) life he’s able to lead is all due to the sport that he’s grown up with and loves. Basketball, he says, allows him the chance to travel the world and watch one of the nation’s top sports from the front row. It sends him all over the globe, scouting for new talent and making trades and offers throughout the year—the team just returned from a training camp in Quebec City and a preseason tourney in Tokyo—and still gives him time to come back home once or twice a year.

It’s on this most recent visit that Webster reflects. He looks back on his life and the journey he’s taken to get to where he is today.

“There’s not an easy explanation for it,” he laughs, once again marveling at the fact that the journey started with an online application on a whim. “I play a lot of it through my head. Obviously, I’m incredibly lucky. Sometimes I feel this is so far from Kailua, so far from the life I’m familiar with.

“I always want to come back here, but I think once you get a taste of what’s out there, you just want to continue to live it.”