James Francis Stapleton

James Francis Stapleton
James Francis Stapleton passed away peacefully on Thursday, August 21, 2025, at his home in Bonita Springs, Florida, surrounded by his children. He is survived by his four children, ten grandchildren, one great-grandchild, and his beloved companion, Margaret Crabtree. He was predeceased by his wife of 54 years, Margaret Mary Stapleton (née Daly), and his son Brian.
Born on June 30, 1932, in Bridgeport to James Martin and Lucy Veronica (Moran) Stapleton, Jim graduated from Fairfield Prep (1950) and Fairfield University (1954) before earning his law degree from Boston College (1957) and a master's in tax law from Georgetown University (1958) while working at the U.S. Department of Justice's Antitrust Division.
In 1957, Jim married Peg, and together they returned to Bridgeport to raise their family. He began his legal career with Marsh, Day & Calhoun and later served as a member of the Bridgeport Board of Education, Corporation Counsel for the city, and Chairman of the Republican Party. In 1973, he was appointed to the Connecticut Superior Court by Governor Meskill, serving until 1978, when he returned to private practice at Day, Berry & Howard. There, he became managing partner of the Stamford office and built a distinguished career as a litigator, mediator, and arbitrator, continuing his work well into his 90th year.
Jim's professional affiliations included the College of Commercial Arbitrators, American College of Trial Lawyers (Regent), Connecticut Bar Association (President), Federal Bar Council, American Bar Association, and International Mediation Institute. He was admitted to practice before the bars of Massachusetts, Connecticut, the Southern and Eastern Districts of New York, the U.S. Court of Appeals for the Second Circuit, and the U.S. Supreme Court.
Despite his many accomplishments, Jim placed faith and family above all else. He was devoted to Peg, especially during her later years, and deeply proud of his children's and grandchildren's education - particularly their shared ties to Fairfield Prep and Fairfield University.
In his later years, Jim faced Parkinson's disease with courage, choosing gratitude and joy over limitations. He was blessed to share the last decade of his life with Margaret Crabtree, whose love, faith, and companionship brought him immeasurable happiness.
One of Jim's enduring legacies is the family gatherings at Lake George, where "Gramps" fostered lasting bonds among his grandchildren and passed down his values of faith, family, and connection. Those who will carry on his legacy include his sons: James Jr. (Debra) of Gilbert, AZ, Mark (Marcela) of Newtown, CT, Paul of Windham, VT, and his daughter Kathleen of Bonita Springs, FL, and grandchildren Christopher, Lauren, Sara, Jeffrey, Shannon, Erin, Caitlin, Caroline, Megan and Kevin, and great-grandson Luke.
Calling hours will be held at Spadaccino and Leo P. Gallagher & Sons Funeral Home, Monroe Turnpike, on Wednesday, September 17 from 5-7 p.m. A Mass of Christian Burial will be held at St. Teresa Church, Main Street in Trumbull, on Thursday, September 18, 2025, at 10 am. In lieu of flowers, please consider making a donation to The Parkinson's Foundation or Leukemia Research Foundation. www.spadaccinofuneralhome.com