That the Raptors hadn’t made the playoffs in five seasons hadn’t dissuaded Ujiri from leaving Denver to become Toronto’s general manager in 2013. He saw it as a unique opportunity to build a winner. And he assembled his own Avengers-style cast of relatively young and unknown front-office talent to join him.
Ujiri’s new hires had a diverse range of superpowers, and each would play a role in building out his vision for the franchise. Weltman, VP of basketball operations, was a front-office veteran and Ujiri’s right-hand man. Keith Boyasrky, the Raptors analytics mind, took over that department as director. Dan Tolzman was a young scouting guru who’d worked for Ujiri with the Nuggets, who came in as director of scouting and player personnel. Teresa Resch, the VP of Basketball Operations, was the self-described “glue-guy”-type and a key player in the NBA’s international basketball programming for several years. Resch sat around the corner from Webster when they both worked in the NBA’s head office, back when they were both doing low-level grunt work.
Even though Ujiri wanted Webster for his experience with the NBA’s new salary cap rules, Webster wasn’t content with that job alone. He could have done that anywhere — back at the league’s head office, he was basically doing it for every team.
If Webster was going to leave New York, he wanted more than a job: he wanted an education. He wanted to learn how a team was run on the inside. He wanted to scout, he wanted to deal with coaches, he wanted to interact with the analytics staff. Ujiri agreed. If Webster provided his salary cap insights, Ujiri assured him that he could work on whatever else he wanted. He even let Webster make up his own job title. He settled on “vice president of basketball management and strategy.”
At the time, Lauren had quit her job in private equity to start her own New York-based company, Negative Underwear — which she founded with a friend that year. Her goals were in New York.
She made a spreadsheet calculating the amount of time she and Webster would actually spend together if she moved to Toronto too. Webster was going to be on the road much of the time, for games and scouting trips. So it was different dreams in different cities, for now.
Webster rented a loft in an old candy factory in Toronto’s Queen Street West district. He lived next to Trinity Bellwoods Park, a large green space next to trendy restaurants and stores where young adults sip cans of craft beer and play frisbee. He spent four years there, just another anonymous 20-something on Toronto’s busy streets, while helping turn the Raptors from a perennial loser into a championship contender.
Webster had been an asset to Ujiri and Weltman in his first few seasons behind the scenes. It wasn’t just that he had an encyclopedic knowledge of intricate salary cap regulations and loopholes. He also had a remarkable understanding of the structure that other teams were dealing with, Ujiri says. He understood how to connect what other teams really needed with what the Raptors’ objectives were. That process usually takes time, but Webster came up with answers almost immediately. Weltman calls him a “savant” in that regard. If Ujiri told Webster that he wanted to acquire a specific player and wanted to know how a possible transaction could work, Webster quickly ran through their options.
But Webster was doing much more. Along with current assistant GM Tolzman, Webster was deeply involved with uncovering unearthed talent, says Ujiri, who has a deep scouting background of his own.
For all its recent success, the Raptors scouting department is actually quite small, with only three full-time scouts to find talent in college, in international programs and within the NBA. Those scouts filter through every kid who has a hope of playing in the NBA and share their thoughts with Webster and Ujiri, who decide which players they want to watch further. The Raptors front office is known to often travel in packs to watch games, even in Europe.
Webster has always followed college basketball closely (even when it wasn’t his job) and in some cases he’ll have his eye on a player on his own.
When he was younger, Webster often attended basketball events that came to Hawaii — like the Nike High School showcase events, and the now-defunct Big Man camp, where NBA and college players would come to work on their skill and footwork, and NCAA tournaments.
When Webster was home in O’ahu over Christmas break in 2014, he scouted at the Diamond Head Classic, an annual NCCA invitational in Honolulu. This time he brought his father to a game between the University of Hawaii and the Wichita State Shockers.
They watched a junior named Fred VanVleet run the floor for the Shockers in a thrilling, one-point overtime win. Webster already had his eye on VanVleet, after he and then-assistant coach Nick Nurse watched him practice earlier that year when Toronto was in Wichita Kansas to play a preseason game. (Nurse was good friends with one of the Shockers’ coaches.)
But Webster won’t take credit for “finding” VanVleet and making him a Raptor — just like he won’t take credit for any of the decisions that look strong in hindsight.
He says everyone in the front office has a crazy story about where and how they first watched Fred play.
Ujiri and Weltman watched VanVleet score 23 points in a Sweet 16 loss to Notre Dame in Cleveland, a few months after Webster and his dad had watched him in Hawaii.
And beyond that, Webster says, when it comes to prospects, everyone in the front office takes the credit for successes and the blame for failures. That might sound like a cliché, but Webster argues that it’s actually fundamental to how the Raptors have built their team.
“We cross-check each other and discuss each player ad nauseum as a group,” he says. “Our decision-making process isn’t set up for one person to rule any decision.”
When it came to VanVleet, everyone involved in scouting watched him play and evaluated him.
At the 2016 NBA Draft, VanVleet slipped off the board. The Raptors had a chance to pick him up in the pile of prospects trying to find the best Plan B landing after going undrafted. Webster (still VP of whatever-he-made-up) and Tolzman (then director of player personnel) were on the phone at 1 a.m. deciding between VanVleet and another undrafted player to offer a summer league contract too. In the middle of the night, they bet on Fred. Tolzman offered VanVleet the contract and he accepted.
“It’s a long, lucky, arduous path to get to our end points,” Webster says.
In his first season as general manager, Webster worked hard to be connected to every department in the front office, including the analytics team, the scouts and the coaching staff. He wanted the best information possible to make decisions for the team. As a manager, he enabled staff to excel at their jobs while taking on new challenges. He led the way Ujiri has.
“He does a great job of bringing people along,” Ujiri says. “It’s how I want it to be because we won’t all be here forever.”
The Raptors finished first in the Eastern Conference that season, with a franchise-record 59 wins. But the playoffs were another story.
For the third time in three years, Toronto lost to LeBron James and the Cleveland Cavaliers. This time the Raptors were swept in the semifinals.
It was apparent that the team they’d built wasn’t good enough to get through the best in the game. And winning the regular season meant little if it didn’t end with a championship.
Four days after the Raptors’ season ended, Ujiri and Webster walked across the gym at the OVO Centre into Dwane Casey’s office and fired the man who would soon be named the NBA’s coach of the year.
The shakeup was far from done.
A few weeks later the Raptors’ executive team — Ujiri, Webster, Tolzman and Resch — flew to Treviso, a small city in northeastern Italy, which hosted the NBA’s EuroCamp for international prospects. But it was more than a scouting trip. The four went away with the intent of thinking deeply about what they needed to do to win a championship, which was the only goal they cared about. They were meticulous in creating the process they wanted to conduct interviews for the head coaching job. They were all a part of each interview, so they could make an assessment of the same information. Everyone had to have a say in the final decision.
After a brief stay in Treviso, they flew to Lithuania to interview a potential new head coach. It was just a quick trip; a covert detour. They had already interviewed assistant coach Nick Nurse for the job — a nearly four-hour process — but they were still hunting; they had to get it right.
While in Lithuania, the four discussed decisions that would affect the trajectory of the organization, good or bad. Every idea was on the table. The goal was to win a championship, and nothing less.
Sometime during their journey, Kawhi Leonard’s name came up. The Spurs superstar had sat out most of the season with a leg injury and seemed to be on the edge of his time with the organization. Was it possible Toronto could land him? They had some gelato, and stopped in a square. Resch snapped a picture of Webster, Ujiri and Tolzman.
Nurse was hired in a little over a week after they returned. Webster was big on giving him the role. He also wanted to have a close relationship with the team’s new head coach. Nurse had joined the Raptors as an assistant coach under Casey in 2013, and he and Webster were aligned on their vision for the team.
“There is like an assumption that there is some contention between a GM and a coach.” Webster says. “But to me, how are you going to win as an organization if there is contention? There is going to be some inherently, but to me, that’s not my personality. I just don’t think it breeds the most amount of trust. These are just basic relationship things.”
With the rookie head-coach signed, they moved on to the next target.
Webster knew that trying to acquire Leonard was an enormous bet. But they were already all-in on a coaching change. This was the time to gamble. And they already knew the outcome of the status quo. They had five disappointing ends to a season in their minds. That is what drove them: it was a championship or bust.
Webster had a relationship with Brian Wright, then the assistant general manager of the SanAntonio Spurs. They had been interns together with the Orlando Magic. Webster had developed a connection with Wright over the years and could speak frankly with his old friend.
“It’s such a competitive business, so relationships matter. Trust matters,” says Wright, who is now the Spurs GM. “Being able to have confidential conversations and work through some difficult things at times. That goes a long way.”
It’s the kind of connection Webster has developed with many people in the industry, Ujiri says — and another one of the reasons he gave him the GM role.
Neither Webster nor Wright will reveal when the first call was made regarding Leonard, but it was sometime after Lithuania, in early June, and it’s been reported that they spoke at the NBA Draft. Regardless, Webster will not accept credit for it. But that initial conversation sparked the biggest trade in Raptors history.
True to the Raptors front office workings, several people were involved in pushing the blockbuster deal that sent DeMar DeRozan — the team’s beloved “I am Toronto” star — to the Spurs for Leonard, the disgruntled, oft-injured enigma of other-worldly talent. As talks continued through July, Ujiri spent a lot of time in discussion with R.C. Buford, the Spurs longtime GM and current CEO. “There are multiple parties involved in something that big,” Wright says.
Before the trade could happen, Ujiri and Webster had to convince the MLSE board to approve the trade, which would take them over the luxury tax and possibly generate a lot of anger from fans loyal to DeRozan. After a long meeting, they came away with the board’s approval.
Ujiri was in Kenya with his friend Barack Obama, attending the opening of a new youth centre, while Webster was home working the final negotiations on the trade. He was in constant contact with Ujiri, who stayed up through the night in Kenya as the deal inched closer to completion. Webster played point on the intricate details of the trade. It was nearly a month of back and forth.
As the discussion got closer to completion, Webster weighed whether it was the right deal to make.
They knew they were going to do something, but did this make the most sense. That existential decision had already been made. But did it involve the right pieces? The Raptors would give up DeRozan, along with promising prospect Poeltl and a first-round pick for Leonard and Danny Green. There could have been many other variations.
Was this the right one?
“You only get one chance to do a deal like that,” Webster says
And he’s thought about pushing further in his career. But at what cost? What sacrifice? And about what kind of voice he should take on as an Hawaiian and as a Japanese-American — what example does he set, and what responsibility does he carry?
A man of goals, driven by a calculated process, Webster seems uncertain about what direction his young adventure leads.
“What do I want to do?” he says. “Where do I want to go?”
Is his ambition to become the president of a team, like Ujiri? To head back to the NBA head office? Or start from the bottom in a new industry entirely. Maybe circle back to the CIA. Or open a food stand on a beach in Kailua, as Webster — a talented cook — has long joked he would.
There is truth in the jest, though. Webster wants his children to know what it means to be Hawaiian. And one day, he thinks, he’ll end up back where he started.
Webster looks down at his phone — the one he uses to run the Raptors. He texts with the players and staff regularly. He’s received a message from one of the team’s young prospects. It doesn’t have any capitalization.
“It’s how young people communicate these days,” he says, and laughs.
Once the NBA’s youngest GM, Webster is feeling old.
A few weeks later, Webster stands on the sidelines at Scotiabank Arena during the 2019-20 season opener, watching a montage of the Raptors becoming NBA champions. He feels the energy of the packed crowd, in a way he hasn’t since the Finals — back when he still couldn’t process what was unfolding.
Cheers rise with flashes of each player and every iconic moment. The entire arena relives the suspense of the bouncing ball on Leonard’s Game 7 winner from the corner. But Webster doesn’t get emotional until seeing the clip of VanVleet’s wild roar after hitting his final three in Oakland to put the Raptors up for good.
The crowd erupts for Ujiri when he’s called to receive his championship ring from NBA commissioner Adam Silver. Webster goes next — to loud cheers, but less so, not that he notices or cares. His diamond-gilded ring is engraved BW, which is what the players call him. He stands off to the side, watching each of them called out, getting goosebumps as the crowd reacts.
When the ceremony is over, Webster takes his place in the stands, next to Lauren, a dozen rows up — where he always sits. His phone lights up with messages and screenshots of him getting his ring on TV from people across his Ohana. Webster bobbles the glistening rock back and forth in his hands.
On the court, Marc Gasol loses the tip-off and the Raptors season as NBA champs begins. Webster takes his seat and fades into the crowd, an island in the great wide sea.
