When you think of baseball in North Haven, you think of Bob DeMayo. It’s hard not to considering that he served as the head coach of North Haven High School baseball team for the past 64 years. DeMayo recently retired from his role as head coach, but not before helping the program, hundreds of athletes, and the town of North Haven reach new heights in the sport of baseball.

It wasn’t an easy decision for DeMayo to step down. He loves coaching and came back every season because he felt he could make a difference in the lives of his players. However, over the past few years, DeMayo has dealt with numerous health issues, including prostate cancer, arthritis, and spinal stenosis. In stepping down, DeMayo wanted to ensure that North Haven baseball was still getting the support it needed and would continue seeing the success that everyone has come to expect from the program.

“I’ve always said I’ll know when it’s time when I couldn’t do the things that should be done or we weren’t having the success we should have because of something physical or mental,” DeMayo said. “The last couple of years have been really difficult. Physical things were preventing me from helping our kids the most. I’m trying to deal with it, because I know I’m going to miss it.”

DeMayo played his high school baseball at Notre Dame in West Haven. After graduating, he went on to play for Fordham University. He was signed by the Baltimore Orioles and played one year of professional baseball. Then he received an offer from his old high school coach John Janenda.

Janenda told DeMayo that if he ever wanted to teach or coach, he had positions waiting for him. DeMayo wanted to be a professional baseball player, but he was married and on the precipice of starting a family. While it was a tough decision, DeMayo decided to accept Janenda’s offer and become an assistant coach at Notre Dame.

DeMayo knew that he wanted to coach from his time in high school. Alongside baseball, he also played basketball and football. DeMayo said Janenda was a huge inspiration for him, and that when he watched him coach, he wanted to emulate him.

“I knew it when I was in high school. I played three sports. I never had a day off. Every year, we had different coaches until John Janenda stepped in,” said DeMayo. “He was a three-sport coach, and I thought that’s what I would do.”

DeMayo got that opportunity at Notre Dame. He not only coached baseball, but also served as the JV basketball coach and spent one year as the head coach of track and field. However, with his family in mind, DeMayo knew that he needed more benefits and more job security. In 1957, DeMayo started teaching and coaching in the town of North Haven, where he currently lives.

He wasn’t the head coach immediately. At the time, DeMayo was teaching social studies while serving as an assistant football and basketball coach. One year into his tenure, various high school coaches were moved into new roles. Specifically, Mike Vanacore was moved from the head baseball coach to the head football coach. That’s when DeMayo was hired as North Haven’s head baseball coach, beginning his tenure in 1959.

“I went to North Haven because all of the coaches at Notre Dame needed some security. I loved teaching there. It was my high school. I probably would have stayed here. But I was married and I knew we would be starting a family,” DeMayo said. “I applied for the job at North Haven without any guarantee that I was going to be a coach. They told me that if the position came up, I got it. After one year, there was a shift in coaches. They gave me the varsity baseball job.”

When he became head coach, DeMayo went to work on implementing his system. He wanted North Haven to play a brand of “smart ball” that included taking pitches and laying down bunts. Alongside their work on the field, he wanted his players to work as a team and be dedicated to playing for North Haven. From that first year, DeMayo saw his players buy into his system, helping the program climb to new heights on the diamond.

“I have a system in how I coach, especially baseball. They always refer to North Haven as, ‘small ball.’ That irritates me. It’s ‘smart ball.’ The kids that play for me were going to have to learn to bunt. They were going to have to learn how to take pitches,” said DeMayo. “You have to be a team player. You have to come to practice every day. The kids bought in. They knew what to expect with North Haven baseball. That was part of the success, or maybe all of it.”

Along with his coaching philosophy, DeMayo was able to work with a group of “great athletes and kids” who loved the sport of baseball. DeMayo said that when you have that, along with captains who are willing to help promote those ideals, you have a successful program.

Mike Anquillare was one of DeMayo’s senior captains this year. Anquillare first met DeMayo when his father Mike was the head coach of the West Haven High School baseball team from 1999 to 2014. Anquillare served as the team’s bat boy and remembers the stories his father would tell him about DeMayo. He considered him a legend.

Playing under Coach DeMayo, Anquillare knew he would have to be meticulous. Anquillare knew that he wouldn’t just have to learn to bunt, but that every time he took the field, he would have to play his hardest and show that he deserved to be on the field. With DeMayo as his coach, Anquillare learned about having pride for yourself and your teammates. Anquillare said it’s something that he will always take with him throughout the rest of his career and his life.

Following his senior season, Anquillare was named to All-State and All-Southern Connecticut Conference teams. However, Anquillare said the accolade that made him feel most proud was being the recipient of this year’s Robert DeMayo Scholarship. The scholarship is presented by Coach DeMayo and his wife Bette and goes to a player who is in strong academic standing and a leader in their community. Anquillare was not only proud to receive the scholarship, but felt proud that he had earned the respect of the DeMayo family.

“It was really the greatest honor. I know I went All-State and got all these accolades, but that was the biggest,” Anquillare said. “It showed the respect that coach had for me as a player. That truly means so much when the player gets that much respect from the coach. It was such a great honor.”

On Aug. 8, the North Haven baseball team held a team meeting to try and decide who the captains would be for the 2023 season. At that meeting, DeMayo announced that he was retiring as North Haven’s head coach. Once DeMayo made his announcement, Anquillare stood up and spoke about his coach. Anquillare talked about how much DeMayo means to North Haven’s players and what it means for DeMayo to be the coach that built the North Haven baseball program.

“None of this would have been possible without him. He built this program from the ground up. He made it what it is today. He solidified us as one of the best programs in the state,” said Anquillare of DeMayo. “There’s so many things he has done for North Haven baseball and baseball in Connecticut as a whole. He’ll forever live on as a legend in Connecticut sports.”

When DeMayo stepped down, he did so as the longest tenured coach in Connecticut. Over his 64 years, DeMayo won 937 total games to go with five state championships, claiming the Class LL title in 1975 and 1982, and the Class L crown in 1985, 2003, and 2015. North Haven also made the Class L state final in 2004 and 2017. Additionally, North Haven won 19 Housatonic League championships and two SCC titles with DeMayo as head coach.

In 1975, DeMayo won his first state title with North Haven when the team defeated New Britain, which was undefeated at the time, by a 1-0 score in the Class LL state final. It was a nine-inning game back then, and Mike Proto pitched all nine innings for North Haven. As he looks back at his career, DeMayo said that he will always remember that first state championship victory.

“It was one of the best games ever,” DeMayo said. “We faced a kid from New Britain, who was 25-0. I had Mike Proto, who was 9-1. We came out on Yale Field and won 1-0. It was an unbelievable game. It was one of the classics.”

Proto had been playing for DeMayo since he was 12. DeMayo coached Proto at the Little League level before Proto played for him at high school. DeMayo’s son Gary was one of Proto’s teammates back in Little League and played first base when Proto started the 1975 championship game. From the beginning, Proto said that he and his teammates were, “DeMayo Disciples.” Not only did they learn the game from DeMayo, but Proto said that North Haven’s coach always held each player accountable and helped get the best out of everyone.

Proto has seen the North Haven baseball team have plenty of success during DeMayo’s tenure. However, Proto feels that it’s more than just the wins that make DeMayo a great coach. For Proto, one of DeMayo’s biggest strengths is his mental toughness and his ability to help each athlete build on their own mental strength in order to find success.

“The wins and everything speak for themselves, but that’s not what made him a great coach. He built the inner toughness that you would need not only to perform on the baseball field, but in life in general,” said Proto. “He taught everyone on the team to be mentally tough, to hold themselves accountable, to always strive to improve. You left everything out on the field every game. That was success.”

In 1979, Proto was a senior at the University of New Haven and no longer playing baseball. He got a call from Coach DeMayo, who asked Proto if he wanted to coach at North Haven. Proto said he thought about the offer “for about 10 seconds” and accepted. Proto has been an assistant coach alongside DeMayo for the past 44 years.

Proto has had plenty of offers to coach outside of North Haven, but he’s said no to all of them. Proto loved coaching with DeMayo and enjoyed getting young athletes prepared to play baseball for North Haven’s legendary head coach.

“I never left, and I had plenty of opportunities. I could have, but I never wanted to. I enjoyed the process of helping to prepare kids to play for him and to play for North Haven baseball. It was a special thing,” Proto said. “He cared deeply about everyone on the team. He had a big heart. He is one of the toughest individuals I’ve ever been around, mentally. His approach is so different from any other coach. But his teams bought in.”

After playing for him and coaching with him, Proto said that DeMayo has become like a second father to him. He always admired the integrity that DeMayo brought to the dugout. Proto got a firsthand look of what DeMayo did for baseball in North Haven and said that his legacy will always be set in stone.

“Baseball is alive and well in North Haven,” said Proto. “He has been misunderstood. They’ve only seen him during the game. He was extremely loyal to his players. He saw the best in them. North Haven baseball is what it is because of him. The players were proud to play in the program. He will be deeply missed and, as years go by, he’ll be missed even more.”

During his 64 years as North Haven’s head coach, DeMayo has received tremendous support from his wife Bette and three children, Gary, Robin, and Kristen. They have allowed DeMayo to follow his passion and encouraged him to accomplish his goals as North Haven’s skipper.

“They let me do my thing,” DeMayo said. “I would have not been able to do it without my family and my wife, who is my assistant coach.”

In the early 70s, DeMayo began his tenure as the head coach North Haven’s football team, a role he held for almost two decades. However, when he took on that role, DeMayo wasn’t willing to give up his job as the baseball coach. When he was a kid, DeMayo said he would walk the streets of New Haven, hitting bottle caps. He always loved playing the game, had dreams of playing in the Majors, and loved watching his New York Yankees.

However, as the head coach of the North Haven baseball team, what DeMayo loved most was seeing the development of his players. DeMayo loved seeing how far his athletes would come from the beginning of the season to the end of it. For all the passion that DeMayo has for the sport of baseball, he made sure to give it back to the town of North Haven. As he steps away from the North Haven baseball team, DeMayo does so as a man who followed his dreams and a coach who impacted the lives of countless ballplayers.

“Baseball was always my passion,” said DeMayo. “Coaching, you begin the year with a group of 15, 17, maybe 20 players. The biggest thing for me was watching them develop throughout the year. They could do it all.”