Jeffrey S. Hennessey

Jeffrey “Jeff” Scofield Hennessey 

1982 – 2026

With broken hearts and countless treasured memories, we announce the passing of Jeffrey “Jeff” Scofield Hennessey, age 44, of Marshfield, Massachusetts, who passed away on June 1, 2026, at Brigham and Women’s Hospital following a short illness. Born in Weymouth, Massachusetts, in 1982, Jeff was the second child and beloved twin son of the late John E. Hennessey Jr. (“Jack”) and the late Deborah S. Hennessey. Though his time with us was far too short, he filled every year with laughter, loyalty, curiosity, and a spirit that was impossible to ignore. 

Jeff grew up in Plymouth, Westwood, Norwood, and Dedham before eventually settling in Marshfield with the family he loved so deeply. He graduated from Catholic Memorial High School in 2001 and forged a career path that reflected both his intelligence and adaptability. He spent more than a decade in the hospitality industry, where his quick wit, easy smile, and ability to connect with anyone made him a natural. Never one to stop learning, Jeff later turned his considerable talents toward software development, eventually working in the rapidly evolving fields of artificial intelligence and machine learning. He loved solving problems, learning new technologies, and proving that it was never too late to reinvent yourself. 

While Jeff was proud of his professional accomplishments, nothing mattered more to him than his family. He was a devoted father to Kailey Hennessey and her fiancé, Jared Stearns, Jackson Hennessey, and Cameron Hennessey. His greatest joy in recent years was becoming “Papa” to his grandson, Beckett Stearns, who brought a new light into his life and never failed to put a smile on his face. 

Jeff is also survived by his twin brother and lifelong partner in mischief, Ryan Hennessey and his wife, Megan Hennessey, and by his older brother, Christopher Hennessey and his wife, Simone Hennessey. 

He was preceded in death by his Father Jack and followed by his Mother Deborah Hennessey, and by his uncle, Lawrence Scofield. He leaves behind his cousins Stephanie Psenicka and Heather Scofield, his uncle William Torpey along with cousins Erin Torpey and Matthew Torpey. 

His Aunt Janet Lezberg and his cousins Alex Picca and Lauren Czarnota. Jeff also leaves behind three friends who were more like brothers than friends: James “Jim” Shaw, Christopher “Chris” Corsi, and William “Bill” Manley. Together they shared decades of adventures, stories, laughter, and the kind of friendship that only grows stronger with time. 

Anyone who knew Jeff knew that he rarely approached life halfway. He was an avid skier who looked forward to winter with the enthusiasm of a child on Christmas morning. He loved NASCAR, cars of every shape and size, and could often be found tinkering under the hood of a vehicle simply because he enjoyed figuring out how things worked. Just as happily, he could spend that same time sitting beside his children, playing video games, laughing, and creating memories they will carry forever. 

Jeff had a gift for humor that could lighten even the darkest room. He was quick with a joke, a sarcastic remark, or a perfectly timed one-liner. He believed life was meant to be enjoyed and that laughter was often the best medicine—even when no one asked for a prescription. His family takes comfort in imagining that wherever he is now, he has already found a ski slope, a classic muscle car, a gaming console, and someone willing to listen to his opinions about all three. 

More than anything, Jeff will be remembered for his enormous heart. He loved fiercely, protected those he cared about, and showed up when it mattered. His family and friends knew they could count on him for a helping hand, a listening ear, or a joke that was probably inappropriate but always appreciated. 

Though his passing leaves an immeasurable void, his legacy lives on through his children, his grandson, his family, his friends, and the countless lives he touched with his humor, kindness, and unwavering loyalty. 

In lieu of formal services, the family will gather later this summer for a private memorial celebration at Dreamfield Farm, held in honor of both Jeff and his beloved mother, Deborah Hennessey. There, surrounded by family, stories, laughter, and the place they both loved most, their lives will be remembered and celebrated together. 

Jeff’s family asks that those who knew him honor his memory by spending time with the people they love, enjoying a day on the slopes, taking a drive with no destination in mind, playing a favorite game with their children, or simply sharing a laugh with an old friend. He will be deeply missed, lovingly remembered, and never forgotten.