James Edwin Thompson, born May 2, 1939 in New York City, died peacefully at his home in Bend, OR on November 19, 2021 of natural causes. He loved his family unconditionally. He survived his first wife, Francesca M. Thompson, MD, and was lucky to have fallen in love again with his second wife, Holly E. Thompson, who now survives him. He leaves his daughter, Heather (Massimo) Cavalli , son James (Sarah) Thompson, and his stepson Peter (Megan) Bugoni. He is survived by seven grandchildren: Francesca and Luca Cavalli; Nathaniel, Samuel, and Zachary Thompson; Cody and Nina Bugoni. He was predeceased by his parents, Dr. James E. Thompson and Ethel B. Thompson, and is survived by a sister, Elizabeth Binstock, and a brother, Jeffrey Thompson. Jim served two years in the Marine Corps before returning to Yale University from which he graduated in 1964. He began his career in the advertising industry at Benton & Bowles, in New York City, growing with it as he brought his department into the digital age, learning computer languages and writing programs to improve his company. He helped raise his two children and supported his late wife in her quest to become a physician. After her death, he devoted his time to improving his golf game in Litchfield, CT on weekends, and learned to make wonderful bread. Upon meeting Holly, Jim followed her to the Quiet Corner of Connecticut, leaving NYC and Litchfield behind. He was a dedicated member of the Northeast Connecticut Concert Choir. After fifteen years in Brooklyn, CT, Jim and Holly ventured out west where they built a beautiful new home. Always one to find the music, he discovered the Central Oregon Community College’s Cascade Chorale in Bend. Combining his love for both computer technology and music, Jim helped both his choirs by transcribing the music into a digital format for all members to be able to practice at home. He loved singing, his walks along the Deschutes River Trail, his evolving gardens, his new puppy, and his time with Holly. Jim was best known by friends and family for his bellowing laugh, his prowess in the kitchen, his forthright opinions, and his fierce loyalty. He will be terribly missed. Family and friends will gather in Litchfield, CT on May 21, 2022 to celebrate Jim’s life.