James “Jimmy” Michael Connolly, born April 4, 1963, passed away peacefully in his sleep on December 28, 2025.
Jimmy was a quiet but strong man, the kind of person whose love ran deep and steady. He loved his wife, his children, and his dog fiercely, and he showed that love through his presence, loyalty, and action. He was the man who could fix anything, always tinkering and figuring things out. He never thought twice about lending a hand, and if something needed doing, Jimmy was already there, helping before anyone had to ask.
He lived simply and never needed much, yet the impact he left behind is anything but small. The outpouring of kindness he shared with others touched far more people than he ever knew. He will be remembered for his loyalty, his quiet and sharp sense of humor, and most of all, for his deep and unwavering love for his family.
One of Jimmy’s happiest places was the dog park, where he spent hundreds of cherished hours with his beloved dog, Beaux, by his side. There, he made countless friends—both human and four-legged—and found joy in the simple moments that meant the most to him.
Jimmy was the loving husband of Florence “Flo” Lafferty Connolly, the love of his life. He was a devoted father to Shawn and Meghan, whom he loved dearly, and a proud grandfather to Arya and Brayden, who brought him endless light and happiness.
He was a beloved brother to Martin "Markie" and Jane Connolly, Debbie Griffin and her husband the late Jimmy Griffin, Patrick Connolly, Nancy and Joe Lombardi, Bryan and Susan Connolly, Paul and Carol Connolly, Lisa and John Loughlin, Kelly-Ann O’Brien and her late husband Richard O’Brien, and was predeceased by his brother Daniel T. Connolly. Jimmy was also a cherished brother-in-law to Stephen, Jimmy, Paul, Joe, Bobby, Michael, Eugene, Richard, and Mary Lafferty Connolly, and their families.
Jimmy shared a very special bond with his many nieces and nephews, each of whom he adored and who will miss him endlessly.
Though his presence will be deeply missed, Jimmy’s spirit lives on in the lives of everyone he touched—which is far more than he ever realized. Above all, he will always be missed, forever remembered, and deeply loved. We were truly lucky to have him, even for far too short a time.
Relatives and friends are kindly invited to attend visiting hours at The Casper Funeral Home, 187 Dorchester Street, South Boston, Sunday Jan 4 from 12:00-3:00 p.m.
In lieu of flowers donations may be made in Jimmy’s name to South Boston Special Kids & Young Adults, P.O Box 27073, 136 H Street, South Boston, Ma 02127