#10: Usher (Cleveland Cavaliers)
Since 2005, Usher has owned a portion of the Cleveland Cavaliers, so he has seen the team’s highs and lows, including their championship victory in 2016. He was deeply involved in LeBron James’ formative years and witnessed the city’s support of the team through both heartbreak and success. Over time, Usher’s initial $9 million investment has increased considerably. His dedication to the Cavaliers demonstrates both his love for his hometown and his awareness of the emotional impact of the sports industry.

