Thompson, who shares a deep bond with Drake dating back to their shared Canadian roots, described the rapper as family. The former Cavalier noted that his support for Drake remains steadfast, especially after the musician provided comfort following the death of Thompson’s mother in January 2023. During the interview, Thompson emphasized the "Toronto vs. the World" mentality that binds fellow Canadians, including The Weeknd and PARTYNEXTDOOR, in a tight-knit circle of mutual support.
The tension between James and Drake became public knowledge following Kendrick Lamar’s "Not Like Us" release, which James was seen enjoying. Drake later unfollowed the NBA star on social media and alluded to shifting loyalties during an October 2024 concert. While James told interviewer Speedy Morman in September 2025 that he still wishes the rapper the best, the sentiment was not reciprocated. On his recent album, "ICEMAN," Drake targeted James in the track "1 AM In Albany," criticizing the athlete’s history of changing teams and suggesting their paths have permanently diverged. Despite these public jabs, Thompson remains persistent in his role as a mediator, telling Sharpe he is "trying" to bridge the gap between the two.
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