On Saturday, December 28, 2024, loving father and grandfather, John “Jack” Joachim Diffily III of Seven Lakes, NC, died surrounded by his family at FirstHealth Moore Regional Hospital in Pinehurst, NC. He was 91 years old.
Mass of Christian burial for both Susan and Jack Diffily: Saturday, January 11, 2025, at 10 a.m. at Our Lady of Mt. Carmel Church, 90 Euclid Avenue, Middletown, NY 10940, with Fr. Paul “Pablo” Richmond, O.Carm, presiding.
Burial: in the family plot in St. Columba Cemetery in Chester, NY.
Jack is survived by his son, Kevin Diffily of Philadelphia, Pa.; daughters Kristine McKenna of Seven Lakes, NC, and Kelly Diffily (husband Steven Kenney) of Philadelphia, Pa.; and three grandchildren, Ferdinand Sawyer, Kayla McKenna, and Nora Diffily-Kenney. He was preceded in death by his wife of 58 years, Susan “Sue” Diffily who passed away earlier this year.
The only child of the late John J. Diffily Jr. and Helen Dwyer Diffily, Jack was born on September 20, 1933, at Horton Memorial Hospital in Middletown, NY. He grew up in Chester, NY. He lived in the Greycourt Inn, which was situated on the Main Line of the Erie Railroad at the junction of the Newburgh Branch Line. The railroad carried passengers and freight between Newburgh and Greycourt and points along the way. His grandfather and then his father owned the hotel. Jack told his kids that as a child he remembered sitting on Babe Ruth’s lap at the bar.
During his teenage years, Jack would often hop on a westbound train car and go one stop to the Village of Chester railroad station, get off, and walk five blocks to Chester Academy from which he graduated. He attended Orange County Community College and went on to study at Siena College in Loudonville, NY, where he earned his bachelor’s degree. He worked a stint at the Ford Motor Company and then, luckily, found teaching when a teacher went out on leave at a nearby high school. He fell in love with teaching and eventually moved to Long Island, New York, where he taught social studies, and later worked as an administrator in the Lindenhurst Union Free School District for roughly three decades. During that time, he earned a master’s degree from the C.W. Post Campus of Long Island University.
Jack and Sue married on July 4, 1965. They built a home in Smithtown, NY, where they raised Kevin, Kristine and Kelly, and lived from 1967 until 1997.
Given Jack’s close ties to the railroad as a child, it is no wonder that the house in Smithtown abutted the train tracks of the Long Island Railroad. Jack’s job as an educator gave him summers off, which meant Jack and Sue could share their love of travel with their family. Each year, Jack and Sue loaded the kids in the back of the family station wagon (no air conditioning or seat belts) to take multi-week vacations to destinations near and far across the United States.
In 1997, following his retirement, Jack and Sue relocated to Seven Lakes, NC, a place they called home for the last 27 years of their lives. Kristine moved to NC in 2017, and Jack loved having her live such a short distance away. He also loved that she brought his beloved granddog Jasper (who Jack affectionately nicknamed “Woofer” and to whom he was known to give pieces of filet mignon and lamb chops) into his and Sue’s daily lives. Jack was an avid reader, always finishing one book and starting another. He shared his love of reading with Kristine, with whom he exchanged books and favorite authors. Jack was curious and inquisitive and loved talking about history, current politics, and foreign affairs. He was a lifelong Democrat who no doubt is glad he left this earth just before the next presidential inauguration. He was also an exuberant and lifelong Dodgers fan, dating to when they were based in Brooklyn. Over the last several years, he got Kristine excited about the team as well, and the two watched many games together. It warms our hearts that his beloved Dodgers won the World Series this year, the final season Jack had the opportunity to watch. (Kris recounts that a young aide at the facility where he was living for the last few months heard Jack screaming one night and became worried, but it ended up the yelling was because the Dodgers won the World Series!).
Jack was an exemplary husband, father, and human being. He embodied the best of qualities. He was kind and gentle. Unlike many men of his generation, he showed his emotions, was physically affectionate, and expressed his love to his family all the time. In the nine months since Sue’s passing, Jack talked often of his deep love for his wife of 58 years and the sadness her absence in his life caused. Jack always supported Sue, who battled depression and anxiety during the latter decades of her life. Jack was immensely proud of his children’s and grandchildren’s accomplishments as well as the people they had become. Jack was always friendly and interested in people, taking the time to get to know the people he came across in his daily life: the staff at his favorite grocery store (the Fresh Market), the local pharmacy, and his bank. He also deeply appreciated the amazing people that supported him and Sue at the ends of their lives. (Special thanks go to Demetris (De) Horton, Terri Barrett, Regina Atkins, Kate Pomplun, and Teresa Synowiez; your supportive care made his life better, as well as Brooks Brady and all the staff at Paragon: you made Jack feel hopeful and whole again). Jack gave generously to the community by volunteering with Family Promise of Moore County and making substantial charitable donations to a wide variety of organizations. He was a man of faith and a practicing Catholic.
In lieu of flowers, donations may be made in Jack’s memory to one of the many charitable and religious organizations he supported: Family Promise of Moore County (fpofmc.org) in Aberdeen, NC; Moore Free Clinic (moorefreecare.org/donations) in Southern Pines, NC; the National Alliance on Mental Illness (nami.org/home) in Arlington, Va.; Our Savior Lutheran Church (oursaviouronline.org) in Southern Pines, NC; or Sacred Heart Roman Catholic Church (sacredheartpinehurst.org/online-giving) in Pinehurst, NC.
Arrangements are under the direction of Applebee-McPhillips Funeral Home, Inc. (applebee-mcphillips.com).