Webster's career in basketball began off the court. After graduating from the University of Pennsylvania with a degree in economics, he went on to earn his law degree from New York University. He then worked at a law firm in New York City, where he specialized in sports law and represented various NBA players and teams.
In 2006, Webster joined the NBA's league office as an associate in the league's salary cap management department. He quickly rose through the ranks, becoming the league's Director of Salary Cap Management in 2010. In this role, he was responsible for advising NBA teams on salary cap issues and interpreting the league's collective bargaining agreement.
Webster's work at the league office caught the attention of the Toronto Raptors, who hired him in 2013 as the team's Vice President of Basketball Management and Strategy. In this role, he was instrumental in helping the Raptors navigate the complexities of the NBA's salary cap, which played a key role in the team's ability to build a competitive roster.
In 2017, Webster was promoted to General Manager of the Raptors, becoming one of the youngest executives in the NBA. As General Manager, he has been responsible for all aspects of the team's basketball operations, including player personnel decisions, contract negotiations, and salary cap management.
Under Webster's leadership, the Raptors have enjoyed significant success. In his first season as General Manager, the team won a franchise-record 59 games and earned the top seed in the Eastern Conference for the first time in franchise history. The following season, the Raptors won their first NBA Championship, defeating the Golden State Warriors in the 2019 NBA Finals.
Webster's innovative approach to team building and his ability to navigate the complexities of the NBA's salary cap have been key factors in the Raptors' success. His work has earned him recognition as one of the brightest young executives in the NBA.
Despite his relatively short tenure as an NBA executive, Bobby Webster has already made a significant impact on the league. His success with the Raptors has not only helped to elevate the franchise to new heights, but it has also helped to pave the way for a new generation of NBA executives.
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