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07/03/2018 08:00 AMBob DeMayo recently coached his 900th win for North Haven High School (NHHS) baseball—more than any other high school baseball coach in Connecticut’s history. He’s been coaching for longer than perhaps any other coach in the nation: more than 60 years and counting. That includes more than 20 years as head coach of the NHHS football team.
Bob’s 900th win took place at the end of May, when the Indians triumphed over Amity 7-6 in the SCC Tournament quarterfinals on the team’s home field—named after DeMayo.
During his time coaching baseball, the Indians have won a slew of triumphs: 18 Housatonic League Championships, five State Championships, one State Regional Championship, five Hammonasset Divisional titles, six Oronoque Divisional titles, and more. Bob has received countless recognitions to match: Coach of the Year by the National High School Coaches Association, a Gold Key Award from the Connecticut Sports Writers’ Alliance, induction into the National High School Coaches Association Hall of Fame—plus induction into the North Haven High School Hall of Fame, of course.
So what’s his secret?
“The secret for success in baseball is to play offensive pressure baseball,” Bob says. “What I try to do is build a program where offensively what we do is put pressure on the defense by bunting, by stealing.”
It doesn’t hurt that Bob has more experience coaching than any of his competitors. He started coaching in 1956 for his alma mater, Notre Dame High School in West Haven, then came to North Haven in 1957 as the freshman basketball coach. The next year, he was named the junior varsity baseball coach.
However, Bob says there is no one method for success for getting athletes to play their best.
“There’s no magic way,” says Bob, who also teaches social studies and the senior psychology course at NHHS. “Each kid handles pressure a little bit differently. With the years of experience that I’ve had, hopefully I’ve been successful in finding that method of communication that can get them to play.”
One unique motivator turned out to be his impending 900th win.
“These kids were bound and determined that they were going to try and get 16 wins so I could get 900,” he says. “They got wind of the fact that I was close, and that was one of their goals.”
As the landmark win approached, Bob noticed something strange on the fence of the playing field: the baseball team had spelled out “894” on the fence using plastic cups.
“I see all these cups are set in the fence—usually we try and keep everything clean—and I’m thinking, ‘What’s going on?’” Bob recalls. “I wasn’t even thinking about it, I was thinking about getting on to the tournament.”
The team went on to win 19 games, easily fulfilling its goal of spelling out “900” on the fence.
It’s obvious that the Indians support DeMayo, but part of his support is behind the scenes, too. Bob credits his wife, Bette, for much of his success—their 42nd anniversary is this coming weekend. They have a son, Gary, two daughters, Robin and Kristen—and eight grandchildren.
“She’s just been phenomenal as far as being the kind of wife that makes coaches last as long as I do,” he says of Bette. “She backs everything I do.”
“The other part of it is I always have fun,” he adds. “I’ve always been a competitor. I like the three, four months a year when we go out and lay it on the line.”
Before coaching, Bob played baseball, football, and basketball at Notre Dame High School. He went to Fordham University on a baseball scholarship, where he studied psychology. For a couple years, he even played Minor League baseball with the Baltimore Orioles.
Finally, Bob credits North Haven’s kids for having clear goals and a get-it-done attitude that helps pave the road to victories on the field and off it. The only remaining question is: now that he’s hit 900 wins, will he return next year to keep coaching?
“People ask me that question all the time: are you going to keep doing this?” says Bob, who plays golf in his spare time. “I’m pretty certain if I feel, physically, I can handle the job, that I’ll be back next year.”