Leo D. Fahey

Leo D. Fahey, a loving, kind, and faith-filled man, passed away surrounded by his loving family on May 9, 2026 after fighting a courageous battle with cancer. He was a true gentleman, humble, kind and gentle, and was a selfless presence in the lives of many, and his memory will be cherished by all who knew him. 
 
Born to the late Leo and Mary (Jones) Fahey, Leo grew up with the values of hard work, faith, and family that would guide him throughout his life. He was a proud graduate of Milton High School and carried the lessons of his youth into every chapter that followed. Leo was blessed with a warm nature and a steady spirit, and he built a life marked by devotion to others, quiet strength, and a deep sense of purpose. 
 
Leo was the beloved husband of Deborah H. Fahey (Skinkis) of Milton. He was a devoted father figure to his stepchildren, Richard L. Daniels and his wife Carol of Braintree, and Elizabeth F. Smith of Braintree. He was a proud and loving papa to Alexandria, Arianna, Evelyn, the late Jonathan, Victoria, and Matthew. Leo also leaves behind his sisters, Claire McGuirk and her husband Austin of Milton, Lois Judge and her husband Leo of Milton, and Karen Parsons and her husband the late Dean of Braintree. His nieces and nephews Michael Judge and wife Kim of Hull, Susan Judge Burns and husband Brian of Milton, Kelly Judge Faggiano and husband John of Needham, Jennifer Judge Rhodes and husband James of North Easton, Kerry Parsons of Newton, Matthew Parsons of Abington, Kim Kullen Murphy and husband Paul of Hanson and Carl Kullen of Braintree. He was also a longtime friend of Bill W., a relationship that reflected the depth of his commitment to recovery, service, and fellowship. 
 
Leo spent his career as a Railroad Foreman for Amtrak, Mass Bay Community Railroad and Keolis Commuter Rail, where he was respected for his reliability, leadership, and dedication. He approached his work with the same integrity and care that he brought to every part of his life. Those who worked with him knew him as a class act. A man who could be counted on, someone who met responsibilities with calm determination and a strong sense of duty. 

Outside of work, Leo found joy in the simple beauty of life. He loved to walk around Turner's Pond in Milton and take photographs of nature, capturing the quiet grace of the world around him. He treasured his family and had many, many friends, each of whom was touched by his warmth and generosity. Leo had a gift for making people feel seen, heard, and valued, and his kindness left a lasting impression wherever he went. 
 
One of the most meaningful parts of Leo’s life was his service to others through Alcoholics Anonymous. For the past 15 years, he ran AA meetings at St. Michael’s on Saturday evenings, offering hope, strength, and encouragement to countless people. He helped thousands of individuals and touched countless lives through his compassion and steady presence. He was a man of God who lived his faith through action, and his example inspired others to seek healing, perseverance, and peace. His service was not performed for recognition, but from a sincere desire to lift others up and walk beside them in their struggles. 
 
Leo’s legacy is written not only in the family he loved and the work he did, but also in the lives he changed. The countless lives he touched and empowered through his selfless service will forever stand as a testament to his remarkable legacy. His dedication created a ripple effect that reached numerous families and individuals who remain grateful for his compassion and generosity. Among those he helped was someone whose life was profoundly changed by his kindness and understanding. Fourteen years ago, on a Thursday night, that person found themselves at Saint Elizabeth Church feeling shattered and lost after twenty-six years of sobriety. In a moment of deep vulnerability, Leo listened with patience, recognized the pain, paused the proceedings, and encouraged that person to share their story. That night became a turning point, and the strength that followed was made possible in part by Leo’s compassion and belief in the healing power of honesty and fellowship. Stories like this reflect the extraordinary way he lived his life, always ready to offer hope when it was needed most. 
 
Leo will be remembered as a man who loved deeply, served faithfully, and lived with humility and grace. His gentle spirit, kind heart, and unwavering faith will remain in the hearts of his family, friends, and all who were fortunate enough to know him. Though he will be deeply missed, his legacy of love, service, and compassion will continue to inspire those whose lives he touched. 

Visiting hours will be held at the Alfred D. Thomas Funeral Home 326 Granite Ave. Milton on Thursday May 14th from 4:00-8:00. At 7:00pm there will be an opportunity for family and friends to share their memories “open mic” style. A Funeral Mass will be held at St. Elizabeth Parish Milton on Friday May 15th at 10:00am. Burial to follow at Blue Hill Cemetery.  

**Please note that parking is limited, but there is street parking on Granite Ave and Wood Street, as well as municipal lots in East Milton** 

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