Coach Bob DeMayo, Connecticut’s Winningest High‑School Baseball Skipper and Guiding Force in North Haven Athletics, Dies at 92
NORTH HAVEN, Conn. — Robert “Coach Bob” DeMayo, whose dugout wisdom, football grit and trademark humility shaped nearly seven decades of Connecticut high‑school sports, died July 9 at his North Haven home. He was 92.
The North Haven Athletics Department confirmed the loss, calling DeMayo “irreplaceable.” From 1958 until his 2022 retirement, he piloted North Haven High School baseball to 937 victories—the most in state history—along with five CIAC state crowns, 19 Housatonic League titles and two SCC championships.
From West Haven Sandlots to the Orioles’ Chain
Born Jan. 30, 1933, DeMayo starred at Notre Dame–West Haven and Fordham University before a stint in the Baltimore Orioles’ farm system convinced him his real calling was teaching youngsters, not chasing his own box‑score glory.
Building a Diamond Dynasty
When DeMayo took over North Haven baseball at age 25, the school fielded no freshman team and practiced on a windswept gridiron. By the 1970s his squads were perennial contenders, renowned for crisp fundamentals and a mantra he repeated every March: “Play the game the right way, and the wins will follow.” Even rival coaches applauded his sportsmanship. In 1992, he insisted Derby ace Benjamin Bartone make the All‑Housatonic roster, declaring the left‑hander “as good as anybody in this league.”
A Two‑Sport Mentor
Though baseball made him a state icon, DeMayo also served as an assistant on North Haven’s football staff, reinforcing the same disciplines—accountability, resilience, love for the team—that animated his spring practices. Former players recall post‑game buses where Coach quizzed starters and reserves alike, not on box scores but on how they treated the opposing dugout and the home‑plate umpire.
Teacher First, Coach Always
DeMayo touched thousands of lives as an industrial‑arts teacher, counselor and summer‑camp director. Alumni describe handwritten notes arriving decades after graduation, congratulating them on weddings or new jobs. “He was a father figure,” athletic director Steve Blumenthal said.
Late‑Career Milestones and Farewell Tour
In April 2018, DeMayo logged win No. 900; four years later he doffed his cap for a final time as the CIAC dedicated its 2022 state finals in his honor. Even in retirement, he attended off‑season lifts, slipping hitting tips to freshmen and reminding veterans that “wearing North Haven across your chest means giving back.”
Family and Final Arrangements
DeMayo is survived by his wife of 66 years, Bette DeMayo; children Gary (Lucy), Robin (Adam) and Kristen (Gary); eight grandchildren and one great‑grandson. Visitation is scheduled for Tuesday, July 15, 3–7 p.m. at North Haven Funeral Home, 36 Washington Ave. A funeral Mass will follow Wednesday morning at St. Theresa Church; interment will be private.
An Enduring Legacy
Flags at North Haven athletic venues now fly at half‑staff, but former captain Jason Romano speaks for many: “Coach never measured success in rings or banners; he measured it in the kind of adults we became.” Plans are underway to rename the school’s varsity diamond Bob DeMayo Field and to endow a scholarship for multi‑sport athletes who exemplify his creed: respect the game, respect each other.