The second term — a Hawaiian phrase that means “part” and refers to people of mixed race — described Webster’s Japanese-American background. Webster’s mother, Jean, descended from Japanese immigrants who came to work in the stables at a Hawaiian sugar plantation around the turn of the 20th century. Webster’s father, Bob, a redheaded Chicago native, moved to Hawaii in his late 20s and never left.
While Webster is the only general manager with Asian heritage in a league where fewer than 1 percent of players are Asian, he rejects any notion that he is an outlier. Instead, the easygoing, media-averse executive views his mixed background as a core strength. His exposure to multiple cultures in the small beach town of Kailua, Oahu, honed a work ethic that made him the NBA’s youngest GM, at age 32, when he was promoted in 2017. It also instilled an open-minded philosophy that has helped guide the Raptors through a major transition following Kawhi Leonard’s departure.
“In our household, it was never so explicit: this is Asian, this is white,” Webster said. “There were never limits placed on me. If you’re a white kid, that’s a different experience. If you’re a full Asian kid, you’re like everyone else [in Kailua]. If you’re mixed, you’re cool. We had Jeremy [Lin] on the Raptors and I talk to him a lot. He looks Asian, and [dealing with stereotypes or bias] was much more on someone like him. I don’t think I look super Asian or white. Being both was freeing. Both communities always accepted me. I had the best of both worlds.”
Identity is no simple concept. Webster does not speak Japanese, and he was listed as “Other (Pacific Islander)” rather than “Asian” on the NBA’s 2019 Racial and Gender Report Card.
Yet Japanese culture and customs remain a major part of his life: He counts fried rice among his favorite foods, he removes his shoes in the house and he took the Raptors to Japan for preseason exhibitions in October. While honeymooning with his wife, Lauren, in Tokyo in 2015, Webster was struck by a lifelong tempura chef’s “humility, perseverance and standard of excellence,” and how he could see his family’s “mannerisms and demeanor” reflected throughout a city thousands of miles from his home.
As it happens, the central professional challenge facing Webster this season is a matter of organizational identity. After betting big on a 2018 trade for Leonard, the Raptors claimed their first title in franchise history. A few weeks after the championship parade, Leonard, the Finals MVP and Toronto’s most accomplished player, bolted for the Los Angeles Clippers as a free agent.
When a player of Leonard’s caliber leaves for nothing, bad things usually happen. LeBron James’s 2010 departure plunged the Cleveland Cavaliers into the lottery, a process that repeated when he left the Miami Heat in 2014 and the Cavaliers again in 2018. Kevin Durant’s Achilles’ injury and subsequent exit have played a major role in the Golden State Warriors’ collapse this season.
But Toronto is rolling along in its first season without Leonard, posting a 9-4 record and a strong plus-7.2 point differential. The Raptors have a split personality — battle-tested veterans mixed with hungry youngsters — but have meshed well to play a relentless, entertaining style of basketball. Pascal Siakam, the reigning Most Improved Player, has taken another leap, emerging as a franchise player with a more developed offensive game than he displayed last season.
Meticulous planning helped the Raptors shift gears. Webster, who was recruited by Ujiri from the NBA league office, where he spent seven years working on Collective Bargaining Agreement and salary cap matters, said that Toronto began thinking through the implications of Leonard’s departure before they even acquired him.
When Leonard delivered his verdict in the early morning hours of July 6, the Raptors turned to their contingency plan, which eventually involved re-signing point guard Kyle Lowry to an extension and inking Siakam to a max deal. Those moves helped solidify Toronto’s base and sent the message to veterans such as Marc Gasol and Serge Ibaka that winning, not rebuilding, would be the priority.
“These guys earned the right to make another run at it,” Webster said. “We knew we had a core that could compete. Even if you subtract Kawhi and Danny [Green], we’re still a really good team. There was a lot of [trade] speculation but the plan all along was to keep this team together. Could the arrangement have worked out any better? We won a championship and [Leonard] got to go home [to Southern California].”
Siakam’s development has been an essential driver for the post-Leonard Raptors. The 25-year-old forward from Cameroon was a bit player on offense as recently as 2018. This year, he is averaging 25.7 points per game — 10th in the NBA — and looking comfortable as both a three-point shooter and a ballhandler. A late-first round pick in 2016 who flew under the radar at New Mexico State, Siakam possesses energy, length and improved polish that should make the Raptors a tough out in the playoffs.
For Toronto’s front office, Siakam’s growth is added justification for their decision to gamble on the Leonard trade. Leonard not only delivered a title, Webster reasoned, but he left a “legacy [of knowing] what it takes to win on that level” for a franchise that had previously been defined by its postseason shortcomings.
“I took a lot from [Leonard],” Siakam said, already sounding comfortable in his new, expanded role less than a month into the season. “His poise, how he doesn’t really get rattled. I tried to add that to my game. … When you get to shoot the ball a little bit more, it gets you excited a little bit. I like that.”
As their future begins to take shape around Siakam and OG Anunoby, an athletic 22-year-old forward, the Raptors aren’t rushing. Toronto has won more games than every team besides the Golden State Warriors and San Antonio Spurs since the start of the 2014-15 season thanks to a front office whose style has been defined by tactical strikes rather than wild swings.
Eventually, Toronto will need to phase out Gasol and Ibaka in favor of a younger front line. Lowry, at 33, isn’t a long-term solution at this stage of his career either. To some executives, this might feel like an uncomfortable purgatory: trapped between being a top-shelf title favorite and an inevitable retooling effort.
Webster, though, is wired to reject false dichotomies. Onstage at the U.S.-Japan Council, he warned about “debilitating mental constructs” that can arise when people buy into “specific ideals or limitations” placed on them by their families, friends or even themselves. His message to the young Japanese-Americans in the audience: pursue excellence, and don’t be afraid to be part of a “generation that’s trying to say that you can do what you want and go into a field that is typically dominated by one or two ethnicities.”
The Raptors, in his view, should be similarly unencumbered, capable of learning from the Leonard era while also succeeding outside of its shadow.
“You build a team and staff based on values and principles that you want to live by,” Webster said. “Once you win, you have a shared experience about what [expletive] matters and what doesn’t. How many guys on this team have a ring? There’s a ton of pride in this locker room. [Following a title] is a difficult position to fill, but our guys are competitive as hell. You always take [competing] versus the alternative.”