James Hilary Carpenter

James Hilary Carpenter, 88, a longtime resident of Westport, Conn., died on Monday, Dec. 8, 2025, at his daughter's home in Trumbull, Conn., after a valiant battle with cancer.
Known fondly as Jim or Hil, he was born in Norwalk, Conn., on March 9, 1937, to proud parents Rose Horelick Carpenter and James Townsend Carpenter.
An only child, Jim loved growing up in Westport where he had many fun and memorable adventures with his cousins, including Joe Deluca, Jean Kiser and Gail Kern, and his dear friends, including Noel Castiglia, Don von Liebermann, Sandy Frey and J.D. McMahon.
Whether they were at Compo beach, riding their bikes all over Fairfield County including to Danbury, going to camp at the Westport YMCA with their friend Roddy, hanging out at the Minuteman statue near the beach or spending many hours on his boat on Long Island Sound, Jim always came home with a good story. Jim attended Westport public schools graduating from Staples High School in 1955 where he played the saxophone in the marching band and orchestra, worked on the Inklings newspaper, played baseball and as a nascent artist, drew the cover image for the 1955 Staples High School yearbook.
Jim attended the University of Connecticut in Storrs before enlisting in the United States Army in 1958. He was stationed at Fort Hood, Texas, traveling to Germany at one point. He thrived in the Army and was asked to stay, but chose to go back to his hometown of Westport. Upon his honorable discharge in 1960, Jim taught at the John S. Turner U.S Army Reserve Center in Fairfield for one year. Throughout his life, Jim loved recanting many Army stories to family and friends.
After spending several months driving cross country from Connecticut to California and Mexico and back in a two-seated convertible Austin-Healey Sprite, Jim began his remarkable 26-year career with United Parcel Service. Jim's route in north Stamford opened up a new world where he would meet many remarkable people including Gene Wilder, Gilda Radner, Jackie Robinson, Vivian Vance, and NY Giants' defensive end, Andy Robustelli, who generously arranged for Jim to get season tickets.
An avid lover of sports, Jim particularly loved watching baseball and football. He was a longtime fan of the Dallas Cowboys after watching them play their first games in Texas and meeting their legendary coach, Tom Landry, who gave him and his fellow soldiers front-row seats to watch the new team. Jim was also an avid reader of The New York Times and other newspapers and was always surrounded by his many books, especially ones steeped in American history, politics and World War II, which he devoured.
Jim is survived by his beloved daughters, Karen Ann Carpenter (K.C.) Baker and Jennifer Stella Carpenter, the mother of his daughters, Grace M. Carpenter, and his cherished grandchildren Cameron and Lindsay Baker. He is pre-deceased by his parents, grandparents Stella and Hilary Horelick and Emma and James Carpenter, uncles including Michael Wanat and aunts including Stella Chapman, who was like a second mother to him, Anna DeLuca, Helen Wanat and Nancy Laughlin, and his cousin Brian Wanat, whom he considered "his brother." He leaves behind many loving cousins, including Gail and Joe Hogan, Darlene Dougiello, Dominique Angerame, Barbara and Rick Vlaha, Lynne Kern, Kyle McCormick, and Sean McCormick, his nephew, Jeffrey Tessitore, godson Matthew Bova, and many dear friends.
Jim was an exceptional and loving father who always put his daughters first. He taught them how to ride their bikes and to drive and always gave them sound advice without judgment. He liked to surprise his daughters when they were younger with little toys, candy or comic books. Jim took great pleasure in trying to beat his daughters at water basketball and Jeopardy, telling dad jokes and enjoying Broadway shows, movies and vacations to Bermuda, Barbados, California, Virginia, Massachusetts and other places with his family.
Besides being the best dad anyone could ask for, Jim will be most remembered for his deep love of animals, (he saved many over the years...) helping others, his integrity, and his fighting spirit.
Jim's family wishes to deeply thank Teresa, Claudia, Karen, Bailey, Danielle, and the rest of his hospice team at RVNA in Ridgefield for their incredible care of Jim these last two years and the Dougiello family for their love and support.
Jim will be deeply missed.
Friends may call on Monday, December 15 from 4 to 7 p.m. at the Fairfield Funeral Home of Edmund W. Dougiello, 36 South Pine Creek Rd., Fairfield. A Mass of Christian Burial with full Military Honors will be celebrated on Tuesday, December 16 at 10 a.m. at St. Anthony of Padua Church, 149 South Pine Creek Rd., Fairfield. Burial will be private.
In lieu of flowers, please consider making a donation to Animals in Distress, a no-kill cat shelter in Wilton, Conn. https://animals-in-distress.com.