Bob DeMayo: Coach for a Season, Teacher for Life

When Robert E. DeMayo retired in 2022 at the age of 89, he was lauded as the winningest high school baseball coach in Connecticut history. With 937 wins over the course of a 63-year career, he led his teams to five state championships and nineteen league championships along with being named both State and National Coach of the Year. But as a multi-generational crowd assembled to celebrate the coach’s retirement, it became clear that Coach DeMayo’s legacy wasn’t only about wins, double-steals, and sacrifice bunts. It was about the hundreds of past players who consider the coach among the greatest influences in their lives – who now tell stories not only about victories and home runs but also about learning self-discipline, determination, focus, commitment and loyalty. In this compilation, Bob DeMayo tells his own story, starting out as an Italian-American kid growing up in working-class New Haven, earning a baseball scholarship to Fordham University, and then going on to a long career as a classroom teacher and coach. But Bob’s story is just the beginning, followed by the first-person accounts of more than seventy former players, teaching colleagues, assistant coaches, and family members who offer their insights into how Bob DeMayo influenced each of their lives. He is surely Connecticut’s winningest coach – not just in terms of games won but in terms of the hundreds of people who herald him to this day as one of their heroes. Read more