The Smiling Raptor

Why is Kailua native Bobby Webster grinning so much these days? Maybe it’s because the NBA’s youngest (and arguably brightest) general manager is excited about the upcoming playoffs, where his Raptors are one of the favorites to win it all.

Promising NBA executive Bobby Webster, the youngest person in league annals to be named general manager, has been flashing his pearly whites (as any true velociraptor should) with regularity these days — and for good reason.

Much to his delight, the Raptors have made it a habit of fearlessly baring their choppers and savaging opponents all season long. As a result, Webster has helped give basketball fans living in the association’s only city north of the U.S. border visions of grandeur heading into the postseason, which tips off in less than three weeks. Come to think of it, there hasn’t been this kind of buzz surrounding the Toronto Raptors franchise since a high-flying Vince Carter was doing half-man, half-amazing things in the early 2000s.

“To borrow a line from our coach, Dwane Casey, we don’t know if we’re the best team, but the numbers at least say we’re the best team in the conference,” observes Webster, whose squad, which sits atop the Eastern Conference standings with a 53-19 record at press time, has been on a tear as of late, winning 12 of its last 14 games.

Sharing the ball and the spotlight with Raptors’ president Masai Ujiri last June following Webster’s promotion to general manager.

Of course, how far this pack of ferocious Raptors goes in its hunt for an NBA title remains to be seen. The past two years, the team has inexplicably lost its bite in the playoffs, and there is no guarantee the players will ultimately claw their way to the Promised Land this time around, even with the installation of a dynamic, free-flowing offense built around all-stars DeMar DeRozan and Kyle Lowry. Maybe more importantly, a certain player by the name of LeBron James still roams the East for the Cleveland Cavaliers, and he’ll continue to rule the courts until the Raptors, or some other team, finally rips the conference scepter from his grasp.

“Obviously, LeBron has been to the NBA Finals the last seven years, and we know that he’s our competition, so who knows what the future will hold?” says Webster, a Kailua native and an alumnus of ‘Iolani School. “Still, it’s been a successful season for us and an incredibly fun time to be a part of the Toronto Raptors.”

And that’s precisely why Webster should continue baring his teeth and showing off that brilliant, cherubic smile of his. After all, he deserves to revel in the team’s success — evidence that the Raptors made a wise decision last summer when they promoted him from assistant general manager to general manager. Now, nearly a year older and wiser at 33, Webster is viewed as a contender for this season’s NBA Executive of the Year award. Additionally, his age and acumen are seen as advantages when it comes to appealing to and developing this generation of ballers.

Bobby Webster will gladly pose for a photo with Toronto players Kyle Lowry and DeMar DeRozan. Just don’t ask him to play pickup ball with the all-stars.

“I guess what I didn’t have in experience, I gained in relatability,” explains Webster about one of the skillsets he brought to his current position. “I’m very much within the same generation as our players, and that’s unique because historically, that hasn’t been the case.”


Running an NBA team was obviously not on Webster’s career radar when he graduated from ‘Iolani School in 2002. But playing college ball was. Yet after teaming up with prep phenoms like Derrick Low and Bobby Nash, and helping guide the Raiders to the state basketball title over Kalāheo his senior season, Webster only received offers from Division II and III programs.

Disappointed by the lack of interest from Division I schools, he decided to enroll at the University of California, Santa Barbara, and focus on academics.

“In a sense, my thinking was if I can’t make it in Division I basketball, then just let me get on with my life,” recalls Webster, who would go on to major in economics and graduate with his bachelor’s in three years.

He was only 21 at the time and already looking for a life away from the hardwood. But as fate would have it, the NBA had other plans for him.

Or, as he explains, “During what would have been my senior year, I did a couple of internships, including one in Washington, D.C. I had this friend there and he would take me to these Washington Wizards games for free, and I thought that was the coolest thing. I was like, ‘How are you getting these free tickets?’ and he said it was from the company he was working for.

Then he said, ‘You know, if you like basketball so much, why don’t you do something in sports?’

“So, I moved down to Orlando and I’m working and kind of on my own, when one day, just by happen-stance, I found myself sitting next to the assistant GM and some scouts for the Magic. I started picking their brains on what they did. That’s when I realized there was this whole other world of the NBA that existed.

“I knew then what I wanted to do.”

Webster landed an entry-level job with the Magic before league officials in the New York office began to recognize his talent, particularly his grasp of league economics. He was offered a job as a staffer in 2007, and eventually named associate director of salary cap management, a position that required he serve on the NBA’s Labor Relations Committee and assist with the league’s collective bargaining agreement. Working on the old CBA — a contract between owners and the NBA Players Association that advises the league’s 30 teams on matters such as salary cap management, revenue distribution, the NBA Draft, player contracts and trade proposals — turned out to be the perfect training ground for Webster, as he familiarized himself with the association’s myriad policies and regulations.

When the NBA went through a contentious lockout between owners and players in 2011, Webster suddenly found himself serving as a principal architect of the new CBA. Then, once the strike ended, he became a highly sought-after commodity for team presidents looking to reconstruct their rosters. From their perspective, who better to navigate the new CBA than someone whose fingerprints were all over the contract’s complicated and fresh set of rules?

“I’ve always believed that my time in New York helped mold my mind as I assisted organizations in building their teams,” Webster opines. “For example, when (Toronto Raptors president) Masai (Ujiri) was working in Denver, I helped him and the Nuggets at different times complete deals. That’s how I was able to build my relationship with him and with people on different teams. People started looking at me and saying, ‘Hey, maybe this kid kind of knows what he’s doing?’

“And so, after years of working in the NBA office and going through every trade, every contract signing, every waiver and every transaction that happens, I wound up figuring out ‘the best way’ to build a team.

“That’s why I always say that my time in New York ultimately gave me job security.”


When Webster was serving as Toronto’s VP of basketball management and strategy in 2015, he met and fell in love with New York resident Lauren Schwab, the co-founder of the lingerie line Negative Underwear. The couple would tie the knot that summer during a lavish four-day ceremony that was divided between the bride’s parents’ home in Southampton and LongHouse Reserve, an exclusive 16-acre sculpture garden that hosts no more than two weddings a year.

Today, the lovebirds make their nest in Toronto, but according to Webster, they “try to get back to Hawai‘i as often as we can” to visit his parents, Bob and Jean, in Kailua and make highly coveted food runs to Helena’s Hawaiian Food in Kalihi.

“Lauren and I first met when I moved to New York to work with the league office,” explains Webster when asked about his family life. “We were really young at the time, but fortunately, we were able to grow up together, which has enabled us to do what we do now. I’m always traveling and busy, and Lauren has to go back and forth to New York to take care of her lingerie business. But because we developed a strong base in our relationship when we were so young, we’ve been able to maintain our independence while always knowing that we have each other.”

Not to mention the presence of a little one to help keep their union strong.

Last June, just days after Webster was elevated to his current position within the Raptors front office, the couple welcomed their first child, a boy named August, into their lives. August’s arrival put a cap on a memorable summer for the young family.

“We just took him to his first NBA game the other week at Madison Square Garden,” says Webster, still giddy over the milestone moment. “He lasted for about a quarter and a half. By then, it was sensory overload for him and he was ready for nap time.”


Despite a hectic lifestyle, Webster still finds time to play pickup ball with fellow staffers and occasionally on an inner-city league team. But what you won’t find is him hooping it up with professional players. No way.

“When you see those guys and how fast and how skilled they are, it’s a reminder of why I should stop playing,” he admits, laughing.

Thankfully, his job isn’t dependent upon him scoring buckets in pickup games; rather, it’s in finding quality players and coaches, and building championship-contending teams.

“As management in the front office, the goal is sustained success,” he says. “So it’s not just how do we win a championship this year, but how do we contend for the next 10 years.”

Competing in a profession in which the stakes are incredibly high requires almost non-stop travel for Webster to U.S. college campuses and European gyms, to scrutinize both amateur and professional players and weigh whether they have a future in a Raptors’ red, silver and black jersey.

“You’re constantly scouting college players, monitoring professional players who may be available for trade and evaluating the team to figure out how to get better,” says Webster about his duties.

Not that he’s complaining about the demands of his job. As he likes to say, “at the end of the day, I’m just lucky enough to be paid to watch basketball.”

And that’s reason enough for Toronto’s general manager to keep on smiling.