By Carol Masshardt

(The series will feature 2024 high school graduates from South Boston)

Thomas, “Tommy” Flaherty, 18, will soon be graduating from Archbishop Williams High School. He has lived in South Boston all of his life, and it seems he knows every street and blade of grass in the community he loves. In the fall, he plans to follow in the footsteps of his older sister, Casey, and join the Coast Guard.

“I knew I wanted to do something different and didn’t want to go to college. My sister really liked the Coast Guard and is an Aviation Electronics Technician (helicopter mechanic) and that’s exactly what I think I want to do. I made the decision last summer, and have support to go this route,” he said. “I hope someday to be in the Boston Fire Department. That’s my long-term goal.”

  The son of Tom and Annmarie Flaherty, he has played sports in South Boston throughout, and has worked at Regan Motivated Fitness for years and was also involved with the South Boston Yacht Club and sailing program. All of this has allowed him a bird’s eye view of trends.

“I love playing sports here but what concerns me is that there are fewer kids in the neighborhood. I wonder who in ten or twelve years will still be saying they grew up here. I do like new people and the people who have been here. They are all nice. It isn’t that. It’s just that I hope people who have kids stay. And the parks aren’t in great condition. We take care of them to be able to play, and I wonder why the city can’t do more,” he said. 

Not one to complain without contributing, Tom and a friend, Stephen Flynn, had a fundraiser for the Senior Babe Ruth Team that helped fund baseball equipment and uniforms. “It went better than we expected,” he said.

Tommy Flaherty could stay put and keep working in familiar territory of South Boston, but he knows there is more.

“I really haven’t been out of the area much. I love meeting new people, though, and I think I will get new ideas and meet people from all over. I want to see how I can handle things by myself. I’m excited but a bit nervous, and one goes with the other with something so new,” he wisely said.

“I guess what I’m most proud of is that I stayed true to myself and didn’t just follow others. I wish I had taken more opportunities to have good friends outside of Southie, but there is more to come.”

Tommy Flaherty, from a many generations South Boston family, has every intention to return, but he is as ready as he can be to step beyond.

“I will be near water, some kind of water, in the Coast Guard and that, naturally appeals to me. And I might have some cool helicopter stories,” he said.

It is likely that Tommy will bring the same respect and determination to new experiences that he has to date. Plus, he will undoubtedly be back with stories of new seascapes, people, and helicopters.

Congratulations, Thomas Flaherty!

(If you are, or know of another graduate who is willing to share their experience, please contact