Home Run with Yankees’ Brian Cashman

The Center for Leadership’s Lunch & Lead with SLS parent and Yankees General Manager & Vice President Brian Cashman drew a large group on Wednesday. Eighty Upper School students, faculty and staff listened intently as Cashman described growing up on a horse farm in Kentucky and playing baseball in his youth. It's noteworthy that while Cashman is a lifelong baseball fan, he was not always devoted to the Yankees—but eventually he changed his stripes. His years at the Yankees started with an internship, and he worked his way up from there. “It’s okay not to have a game plan for your life,” Cashman said but quickly added, “But it's not okay not to do your best. Whatever you're doing right now, you have to do your best.”

A high point for the audience was when Cashman passed around his 2009 World Series ring. He encouraged the students to try the ring on (it’s one of five he has won with his team). One audience member asked Cashman about his job's greatest challenges. Cashman responded that learning how to delegate and “not control everything” was a challenge for him. Someone else asked, “What’s the best part of your job?” Cashman had a one-word answer: “Winning.”