Masai Ujiri gets all the headlines, but Toronto Raptors general manager Bobby Webster is just as responsible for all the moves the team have been making. Yet we still have to figure out who the international man of mystery truly is.
Each time the Toronto Raptors make moves, it’s usually Masai Ujiri’s name that pops up. Although many would be surprised to hear he is the President of Basketball Operations, not the General Manager.
That title belongs to Bobby Webster, the youngest General Manager in the NBA’s 71-year-history.
A Smiling small-town Kid from Hawaii
Webster was born in Oahu but grew up in Kailua, a small town in Hawaii with a population of just over 12,000. Although known more for its football and surfing, Webster pursued basketball.
"“I grew up going to the beach a lot, but I went to the gym a lot more” – Bobby Webster"
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He graduated from Lolani in 2002 teaming up with prospects Derrick Low and Bobby Nash to lead his high school team, the Raiders, to the state basketball title in his senior season. Despite his heroics, he wasn’t offered a single NCAA Division I scholarship. His dreams of becoming a basketball superstar seemed dashed.
Webster instead focused on schooling. He enrolled at the University of California, majored in economics, and completed his degree in just three years.
A Basketball Savant in the Making
Although Webster moved on from having a basketball career, he somehow found himself in the NBA. At just 21, he moved to Orlando and interviewed with executives from the Magic. He landed an entry-level position with the team, until the NBA’s head office in New York realized his potential.
In 2007, Webster became the league’s associate director of salary cap management and helped with the old Collective Bargaining Agreement. Webster familiarized himself with the intricacies of how the association dealt with player salaries along with its complex policies and regulations.
"“I’ve always believed that my time in New York helped mold my mind as I assisted organizations in building their teams” – Webster"
At just 26, Webster became a principal architect of the new CBA thanks to the 2011 NBA lockout. Once the strike ended, he became a hot commodity.
Several team execs looked to him to help them reconstruct their rosters. Among them was Ujiri, who was working with Denver. Webster helped the Nuggets and several other teams properly build a team.
When Ujiri took over the Raptors in 2013, he hired Webster to become the team’s new Vice President of Basketball Management and Strategy.
Four years later, Webster became the team’s new General Manager.
Future President and Maybe More?
In just over a decade, Webster went from being a college graduate to the General Manager of the NBA’s 12th-most valuable franchise.
Webster mirrored baseball’s Paul DePodesta who became an assistant GM of the Oakland Athletics at 27-years-old. Both graduated with economics degrees and kickstarted a new way to analyze their respective sports based on statistics and analytics.
Being the General Manager is challenging. Webster constantly pushes himself to exceed the lofty expectations that come with his job. But amidst the hectic life, the young father of a one-year-old boy named August manages to keep smiling and take life as a GM in stride.
"“At the end of the day, I’m just lucky enough to be paid to watch basketball.” – Webster"
It’s this combination of smarts and poise that gives Webster the makings of something even bigger than a GM. The Raptors are still a top team in the NBA and are stuck with tough contracts. But leave it up to the young gun to cook something up to help the team.
The team’s time with Webster will not last forever and could be over before we even get to truly appreciate him.
As far as front office prospects go, he’s a “five-star talent” and will make it as far as he wants to.