Bobby Webster, the Raptors’ president of basketball operations, is setting a higher standard for the team following the acquisition of Kawhi Leonard, emphasizing the expectation to win every night. At a recent practice, Webster stated, “The expectation this year is to win every night,” and highlighted the importance of competing for a full 48 minutes, moving beyond previous discussions of simply being competitive.

Webster also addressed the trade process, noting that his relationship with the Clippers’ general manager fostered a deal built on “huge amount of trust and respect.” He urged caution against directly comparing this team to the 2019 championship squad, as the current roster, timing, and expectations differ significantly. Leonard's health remains a key factor, but Webster expressed confidence in the decision to bring him back, citing his performance last season.

Leonard signed a two-year, $115 million extension, indicating a desire for a long-term commitment rather than a short-term arrangement. This deal not only provides the Raptors with a star player but also offers flexibility, as they hold first-round picks for the next four years. For now, Webster's focus is on immediate performance, urging the team to establish a new identity rather than relying on past successes.