NORTH HAVEN, Conn. — Bob DeMayo, the revered high school baseball coach who led North Haven High School for nearly seven decades and became Connecticut’s all-time winningest coach, passed away on July 9, 2025, at the age of 92.
Coach DeMayo’s name is etched into the history of Connecticut sports, not just for his record-setting 937 victories, but for the generations of student-athletes he mentored with discipline, respect, and enduring loyalty.
A Coaching Career Unlike Any Other
Beginning his tenure in 1958, DeMayo would coach for 68 seasons, a span unmatched in Connecticut high school baseball. Under his leadership, North Haven claimed five state championships, nearly 20 league titles, and countless playoff appearances. His attention to fundamentals and mastery of strategy made his teams consistent contenders, even when outmatched on paper.
DeMayo’s teams were known not only for how they played—but how they carried themselves. “He taught us to win with humility and lose with dignity,” said former player and assistant coach Mike Busillo. “More importantly, he taught us how to be better men.”
More Than Baseball: A Leader in the Classroom and on the Field
DeMayo also taught psychology at North Haven, bringing humor and insight into the classroom. He coached football for over two decades, serving as head coach from 1974 to 1997. His impact spanned disciplines and decades, shaping student lives well beyond the scoreboard.
Steve Blumenthal, North Haven’s athletic director and a former player, remembered still calling him “Mr. DeMayo” long after high school. “He was a mentor, a father figure, and a coach all at once.”
Character That Stood Out—Even Off the Field
In a moment emblematic of his class, DeMayo once insisted that Derby High School pitcher Benjamin Bartone, a rival athlete, be named to the All-Housatonic team in 1992. “He’s as good as anybody in this league,” DeMayo said, proving again that he valued integrity above rivalry.
His deep respect for players and opponents alike earned him admiration across the state. He was inducted into multiple halls of fame, and in 2025, the CIAC State Baseball Championships were officially dedicated in his honor—a tribute he lived to see.
A Community Mourns, A Legacy Lives On
Coach DeMayo is survived by his wife, Bette, children Gary, Robin, and Kristen, as well as eight grandchildren and a great-grandson, Julius. A public visitation will be held at North Haven Funeral Home on Monday, July 15, from 3 to 7 p.m. A private burial will follow. The family requests donations to the Robert E. DeMayo Baseball Scholarship Fund in lieu of flowers.
Final Inning, Lasting Impact
Bob DeMayo’s legacy transcends championships and accolades. It lives on in the lives he influenced, the standards he set, and the community he helped build. To the athletes he coached, he was more than a legend—he was a guiding force. To his town, he was North Haven.
