The market ecosystem for sports entertainment has exploded in the era of digitalization, social media, online engagements, consumer demand, and even cultural activism. Growing connections to commerce, music, movies, and TV shows have reaped tremendous benefits for numerous industries. Consequently, sports talents can't just be athletes; they are pushed to be also entertainers, brand ambassadors, social activists, and cultural icons for both companies and fans. Who are the winners and losers as sports increasingly evolve into entertainment? What's the impact of this trend on athletes, owners, and shareholders?