Sports Person of the Week seems like a significant understatement for someone like Bob DeMayo. Sports Person of the last six decades is more appropriate. The Connecticut native coached the North Haven baseball team for 64 years before retiring after this past spring season.

The North Haven baseball community came together to celebrate DeMayo’s legendary career on Nov. 13 at the Wallingford Country Club. In attendance at the historic event were countless former players and colleagues — generations of baseball players who have played under DeMayo’s tutelage. Bob talked about how special it is to be celebrated by the North Haven Baseball family, a family, and community that he was instrumental in shaping over the course of an unforgettable 64-year career.

“When you start coaching, you’re out there just trying to win some baseball games,” says Bob. “I began to get feedback from a lot of my baseball players, it was something special.”

Joining him at the event was Bob’s wife Bette, who remarked on how fundamental her husband has been in the lives of so many of the former players in attendance at the celebration. “Listening to some of the kids — although they’re not kids anymore — that were at the celebration, they all pretty much said the same thing,” says Bette. “They learned lifelong lessons on how to live their life through baseball.”

Bob was moved by the event and proud of the impact he has been able to make on so many young ball players. He is grateful for the support his players have given him in turn. However, when he thinks back to his origins at North Haven High School, his motives were simple: “I just wanted to win some baseball games,” Bob says.

Win some baseball games he surely did. After a career beginning in 1959 and spanning over 64 years, DeMayo retired in Spring 2022 as the longest-tenured and winningest coach in Connecticut High School Baseball history, winning 936 total games. He led North Haven to seven state championship games and won five, taking home the title in 1975, 1982, 1985, 2003, and 2015.

Bob has preached patience to his players for decades, instilling a “take a pitch” attitude that produces patient hitters, frustrated pitchers, and ultimately, baserunners.

“Our system was based on getting the first two hitters on base,” says Bob. “If I let kids go up to the plate and don’t get them to take a strike, they’ll swing at anything…the innings would last about 30 seconds long.”

Having been a catcher in his playing days, Bob says the most difficult outs to get were always players who were patient at the plate. “I’ve played and coached in thousands of baseball games, says Bob. “Nobody who is a hitter likes to go up there and take a pitch…. [but] the toughest outs were the ones that would take a strike.”

This upcoming season will be the first in which Bob will not be coaching baseball since before Alaska and Hawaii became US states. Bob will not miss the cold, at times snowy practices that mark the very beginning of the baseball season, but adjusting to a spring without coaching will be difficult for him.

“[I’ll miss] coaching. It’s been bothering me now, but I’m trying to put it away, I gave this up because of physical reasons, I just can’t do this anymore physically. But I know that when spring comes, my wife [Bette] and I will go to the games, she’s the best assistant coach you could possibly have. It’s going to be tough.”

In his newly found spare time, Bob can be found doing what he loves – thinking about baseball. He’ll be talking about the game now and how it has changed and critiquing his beloved New York Yankees from the stands.

Bob remembers specific plays through his career with clarity, from the 1-0 shutout in his first state championship, to a triple play ending a different promising season in the semifinals. He can take you through various scenarios from any point throughout his career, such as rain delays in key innings, or decisions on whether to bunt or not.

“I’ve seen them all clearly,” says Bob. “The variables are all there, the little rock in the infield, where the ball is hit, a blooper wins the game, a line drive is a triple play. It’s that kind of a game, and that’s what makes it great.”

Throughout his career, DeMayo was joined in the dugout by many assistant coaches, often coming from previous North Haven teams. An especially meaningful assistant to Bob is also retiring with him this season.

“I’ve had great assistant coaches, most of them were ball players that played with me. Mike Proto, he’s been with me and done a phenomenal job. I’ve had a lot of people with me, but Mike stands out.” Mike was also the pitcher who threw 9 scoreless innings in the 1975 State Championship, which was DeMayo’s first state title as a coach.

Succeeding DeMayo this spring will be Joe Romanelli, who has been the assistant varsity coach at Notre Dame – West Haven since 2016. Notre Dame is where Bob played high school ball and where he first coached prior to taking the North Haven job. Bob and Joe plan to meet before the season starts. Bob has a simple word of advice for him — be yourself.

“Do what you think you should do, Bob says. “We have a system and I think it’s the best system, but I would never force it on anyone…whatever works for him, and he’ll find out fast.”

While Bob won’t be in the dugout, the DeMayo legacy will continue within the Nighthawks program. Each year, a North Haven player receives the Robert DeMayo Scholarship for leadership on and off the field. Parents sold coffee at games to begin the fund, and the DeMayos have continued the scholarship each year alongside the Tomahawk Booster Club. Bob and Bette plan to continue the scholarship this year and beyond.