James Gregory Jackson

It is with deep sorrow that we announce the passing of James Gregory Jackson, who departed this life on January 30, 2026, at the age of 65. He was born on January 22, 1961, in Portsmouth, Virginia, and spent his formative years moving around due to his father's service in the U.S. Navy, ultimately settling in Ledyard, Connecticut, where he would spend the majority of his adult life. In 2010, he relocated to La Vergne, Tennessee, with his partner and soulmate, Mary Cowland, fulfilling a lifelong dream to return to the state where his father was born and retired.
James was a dedicated family man, cherished brother, and beloved friend. He is survived by his brother, Paul Jackson; his son, James Stephen Jackson; his beloved grandson, Griffin James Jackson; his partner, Mary Cowland; stepdaughter, Bobbi-Jeanne Cowland; and numerous nephews and nieces who will miss his warmth and humor. He leaves behind his two favorite cats, Danny and Doug, who were his loyal companions and provided him with much joy.
Preceding him in death were his father, Robert Richard Jackson; his mother, Diana Mae Walters; his brother, Robert Richard Jackson II; and his sister, Deborah Jackson. Their memories were held dearly in his heart, and he often reflected on the love they shared.
James was known for his many hobbies and interests. He had a passion for collecting diecast cars, watches, hats, and pens, and was an ardent fan of the Pittsburgh Steelers and NASCAR-rooting especially for his favorite driver, Kyle Busch. He found solace in his man cave, where he enjoyed watching "The Office" and indulging in his love for cars, particularly classics and hot rods. Landscape work served as a therapeutic outlet for him, allowing him to connect with nature while nurturing his surroundings.
As a handyman with the remarkable ability to fix anything, James was both reserved and humorous. He had an infectious laugh and a unique knack for making others smile, despite sometimes struggling to express the depth of his big heart. He took immense pride in his work and appearance, and no matter the circumstances, he always prioritized caring for his family. The bond he shared with his son James deepened as they created lasting memories together, particularly during the summer of 2025 when they became best buds.
James's professional legacy includes being named Employee of the Year in 2000 at Foxwoods in Ledyard, Connecticut, a testament to his hard work and dedication during his nine years there. His commitment to excellence was evident in every job he undertook, and he instilled that same sense of pride in his family.
His life was a tapestry woven with love, laughter, and memories. James Gregory Jackson will be profoundly missed by all who knew him, and his legacy will live on in the hearts of those he touched. We celebrate his life and the many ways he enriched our lives. The family has decided to have him cremated and will be taken home to be with his loved ones.
May he rest in peace, knowing he was loved deeply and will never be forgotten.

To send a flower arrangement in memory of James Gregory Jackson, please click here to visit our sympathy store.