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John "Jack" Lefton of Connecticut, passed away peacefully in his sleep on Tuesday, October 28th, at the age of 91.
Born in 1934 in Brooklyn, New York, John grew up in the creative heartbeat of the 1930s-40s, where his lifelong love of art, design, and storytelling began. His mother worked for McCall's magazine and his father for the City of New York, together instilling in him the values of curiosity, craftsmanship, accountability, and devotion to family-principles that shaped every chapter of his life.
John built a distinguished career in advertising, culminating in his role as an Art on Madison Director on Madison Avenue in Manhattan, where his creativity and vision helped shape countless campaigns for companies like Knickerbocker Toys, Toshiba, Rolex, Pfizer and more. Beyond his professional success, he poured his talents into community theater as an award-winning set designer, director, and occasional actor with The Chappaqua Drama Group. His artistry illuminated every stage he touched, leaving a lasting impression on those who shared in his passion for the arts.
As a young father, John raised his first two daughters, Linda and Caryn, with the loving support of his parents, aunt, and uncle while he attended college and started his career. Those years taught him the true meaning of devotion and selflessness, lessons he carried into every relationship that followed. John couldn't have known that his challenging start in Brooklyn 1934 would give birth to a multi-generational legacy of creativity, art, music, service, care, and love that will endure the ages.
In 1968, John met and married Mary Winslow of Scarsdale NY, with whom he built a blended family rooted in love and laughter. He adopted her two children, Tara and Scott, and together they welcomed two more, Gayle and Elisabeth. Family remained the heart of his world, his greatest joy was found in raising his children and later watching his family blossom through generations. He was so deeply proud of his family.
From the 1980s through the early 2000s, John made his home in Westchester County, New York, where he balanced his professional life with volunteer work and his love of community. He was an active member and President of the Chappaqua Drama Group, where he participated in countless productions, like The Mikado, Carousel, Chess and more. He attended First Congregational Church of Chappaqua and First Presbyterian Church of Katonah, where his faith was expressed through quiet acts of service. John participated in Midnight Run, helping to feed and clothe the homeless in New York City, and gave generously of his time and talents to those in need. His kindness was never loud, but always present.
In 1998, John met his beloved partner, Gillian Hugo of New Jersey. Together they shared nearly 25 years of companionship and adventure, traveling the world, hosting gatherings for their large families, and building a warm lakeside life in Medford. They cherished evenings filled with laughter, long conversations, and simple pleasures. Jack and Gill remained devoted to one another until her passing in 2022. He moved to Connecticut to be closer to family. He celebrated his 90th birthday with a big party, surrounded by beloved friends and family.
John was a lifelong artist, film enthusiast, voracious reader, crossword champion, and Jeopardy! fan. A self-taught cook, he took pride in transforming everyday meals into art, evolving from cheeseburgers to fresh, carefully prepared dishes that reflected his attention to detail and love of quality.
Known for his wit, persistence, and boundless curiosity, John could hold a conversation on nearly any topic, and did so with charm and precision. His children treasure memories of their childhood home in Chappaqua, museum trips, Off-Broadway shows, art fairs, and film screenings that opened their eyes to the magic of creativity and culture.
In recent years, John's once active life slowed down quite a bit. But his love and appreciation for his life and his family was ever-present until his passing.
John is survived by his daughters Linda (Don), Tara (Bryon), Gayle (Gino), and Elisabeth (Don); thirteen grandchildren-Preston, Evan, Crystal, Amy, Timothy, Heather, Matthew, Danielle, Thomas, April, Jack, Isabella, and Edward; and four great-grandchildren, Quinton, Xander, Wyatt, and Emma, all of whom we hope will carry forward his wisdom, humor, and artistic spirit. He was predeceased by his daughter Caryn, his son Scott, his former wife Mary, his partner Gillian, and his grandson Jonathan.
A memorial service and calling hours will be held at Carpino Funeral Home in Southbury in the Spring. Following cremation, his ashes will be shared among his daughters in accordance with his wishes.
John's legacy lives on in the love, perseverance, creativity, and spirit of service that his children, grandchildren, and great-grandchildren will continue for years to come.
In lieu of flowers, the family invites donations in John's memory to one of the following organizations dear to their hearts:
Alzheimer's Association: alz.org/donate
Heifer International heifer.org
Monroe Volunteer EMS: Donate via PayPal
Watertown Social Services: Echo Lake Road Watertown CT 06795
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Legacy
John Lefton
March 26, 1934 – October 28, 2025
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