By: Asanka Moehring

Jack Malloy’s life, a tapestry woven with threads of serendipity, sacrifice, and unwavering devotion, is a testament to the power of human connection and the enduring love of family.
Jack’s love story began with a stroke of luck. When his future wife, Phyllis’s suitcase tumbled out of her car, spilling her pajamas onto the pavement, Jack seized the moment. With a playful spirit, he scooped them up and tried them on. This bold move sparked a budding romance that would endure the test of time and across continents. Separated by Jack’s Army service, the couple nurtured their love through heartfelt letters.
“She even waited for me—though she did a bit of dating while I was gone!” Jack joked, his eyes twinkling with affection.
When he returned, he famously quipped about having to “chase the boyfriends away” before they finally tied the knot in 1964. His wife, his greatest partner, remained by his side throughout their lives. Their love story, forged through letters and enduring commitment, became the foundation of their family.
“She waited for me,” Jack said softly, his voice filled with admiration for his lost love. “She was the best.”
Jack and Phyllis’s adventure together began in 1966 when they settled into a cozy Cape on Westwood’s Wildwood Drive. Their home quickly transformed into a bustling hub of love and laughter filled with the joys of a growing family, with four kids – Kevin, Kate, Trish, and Kerry. As the family expanded, so did the need for more space, which led Jack and Phyllis to their forever home, a fixer-upper with a history as colorful as its peeling paint.
“The pool was a mess,” he recalled with a chuckle, “filled with Christmas trees, tires, and even a toilet!”
Through countless hours of hard work, the house was transformed into a vibrant space where cherished family traditions flourished. During the holidays, the home was filled with the warmth of gatherings, and in the summer, the pool became a beloved gathering spot. As Kerry shared with a heartfelt smile, “This house is where we all come together, whether it’s for a holiday dinner or a summer swim. It’s home.”
For Jack, Westwood is more than just a hometown; it’s the heart of his family’s legacy. It’s a place where generations have thrived, holding a special place in his heart.
“When we first moved here, it was a blue-collar town, full of tradesmen like me,” he reminisced fondly.
While the town has evolved over time, with larger homes and new faces, Jack’s love for Westwood remains unwavering. It’s where his children flourished and where his daughters chose to remain, forging an even stronger family bond.
After Jack’s military stint, he pursued a career as an electrician in the Local 103 Electricians Union and embarked on a fulfilling 42-year career. He flourished in his trade, contributing to iconic projects like Deer Island, Gillette Stadium, and Boston’s hospitals.
“I enjoyed being an electrician— as a tradesman, you can always make a dollar, regardless of if construction’s up or down.” Jack reflected.
A true gentleman, Jack continues to foster connections, even as many of his lifelong friends have passed. He embraces new relationships, finding joy in helping others and maintaining an active social life.
“I like people,” he says with a warm smile. “They’re interesting, and I enjoy helping them. If someone needs help, I can give them an hour. There’s no excuse not to.”
Westwood is more than just a town to Jack; it’s a testament to the enduring power of community, a place where he has built a life rich in connection, a life well-lived. He recalled a time when children played freely until dusk, embarked on long bike rides, and neighbors watched over each other’s children – all part of his story-telling nature. Whether Jack is talking about his first car, a temperamental Plymouth, or lending a hand to a neighbor, he embodies the spirit of a true craftsman, building not just homes, but bonds that last a lifetime.
Recent Magazines
SUBSCRIBE TO
WESTWOOD LIVING





















