As a quarterback, Hennessey led Brookline High to a Class A title and an undefeated season in football in 1954. He didn’t stray far from the area after graduating, quarterbacking at Northeastern and becoming the Most Valuable of the Huskies in 1959.
That was the same year that Hennessey began working Little League games. Despite raising six children with his wife Carol, teaching and coaching at Brookline High, and running sports clinics around town, Hennessey never wavered. He always refereed, no matter what happened in his life.
That unwavering quality was on full display Tuesday when Hennessey umpired a Brookline Men’s Softball League game between the Clients and the Big Richards. After calling both teams onto the field, they gave him a round of applause. He left them briefly, before raising his hands and saying, “Let’s play catch.”
Hennessey keeps calling an excellent game. His eyesight is excellent and he moves easily to see the action.
“My health is good,” Hennessey said. “I have been doing this for a long time. I just want to go out on my own terms. I don’t want someone to have to tell me I can’t do the job anymore.”
His wife points out that the daily commute is one of the main reasons for his retirement. After teaching at Brookline High for 43 years, the Hennesseys moved to New Seabury a few years ago, but Hennessey still commuted to Brookline from the Cape several times a week.
“It was the transportation, the hour and a half round trip,” Carol said. “I was worried he was going down the turnpike at midnight. That was a concern. But you can still get the job done, that’s for sure.”
Hennessey’s calm officiating is a constant, and players who have grown up with him as their coach and referee are quick to point it out.
Before the end of the third inning Tuesday, two of Hennessey’s granddaughters caught his eye and he walked over to the fence to say hello.
“Don’t miss any balls,” said one.
Clients catcher Ritchie Allen said, “He hasn’t missed one in 50 years.”
Sometimes Hennessey would come from the Cape not to play, but just to check out the course in bad weather.
“It’s been amazing,” said Bruce Raine, commissioner of the Brookline Men’s Softball League, who has been involved with the league for 30 years. “Jimmy is not only the main referee, he has three or four other referees that he manages. Jimmy takes care of everything for us. Even on rainy days, he comes down to check the field to make sure we can play on the field.”
During the game, as Hennessey calls for a close contest, the crowd grows. Many viewers are his former students and his players at Brookline High. Others remember him from the neighborhood. A woman who grew up with her children rides her bike to the dugout and runs onto the field between innings to give her a hug.
“I heard you were going to be here tonight and I wanted to thank you for everything,” he said, before leaving as quickly as he came.
Hennessey recognizes the impact she has had on generations of young people in Brookline.
“I also enjoyed teaching,” said Hennessey. “I’ve seen generations of players grow up, become adults.”
At the bottom of a hard-hitting seventh inning. Hennessey announces the final out, and attention turns to the postgame handshake between the teams, who then line up to shake Hennessey’s hand.
Last in line is Bobby Allen of Clients, who has known Hennessey for years. He reaches out to Hennessey and proclaims, “You held me all night, but I still love you,” and engulfs him in a hug.
Soon the crowd surrounds home plate. Raine presents Hennessey with a plaque, State Rep. Tommy Vitolo reads a eulogy from the Massachusetts House of Representatives, and Allen brings a trophy. For the first time in its history, the Brookline Men’s Softball Team will have a championship trophy: “The Henna,” named for its Hennessey nickname.
After the introductions, Hennessey calls her brother, Michael, to the plate. It is an appropriate place for him to talk about his home. It doesn’t matter if he’s in the Cape or visiting Florida for the winter, Hennessey will always call Brookline home.
“This is a great city,” Hennessey told the crowd. “I was born and raised here, I spent most of my life here. I will never forget all of you wonderful people, players and fans.
“I never wanted to do it on myself. I just wanted to do the best job.”
After his speech, Hennessey spent most of the evening meeting with those who came to see him, asking more questions about their lives and families than talking about himself.
“I’m leaving tonight, and I’m probably going to be a little sad,” Hennessey said. “I have many good memories. Wonderful people I have met over the years. I will be sad to leave. But it’s time to go.
Kat Cornetta can be reached at [email protected].