Billionaire investor Bill Ackman, known more for Wall Street battles than backhands, is attempting an unlikely career pivot—trying to become the oldest tennis player ever to earn professional ranking points. At 58, he’s chasing a niche sports milestone that’s equal parts inspirational and quixotic.

Editor’s Note: This isn’t just a rich guy’s vanity project—it’s a fun, underdog story that challenges assumptions about age and athletic limits. Whether he succeeds or not, Ackman’s hustle highlights how sports can still surprise us, even at the highest levels. Plus, it’s a refreshing break from the usual finance-world drama.