James Stapleton had the chops to be mayor and even higher. Bridgeport born and raised, he was part of a cadre of young Republicans who formed the Republican Action League that carried Nick Panuzio to the mayoralty in 1971. “Stape” served as Republican town chair, city attorney and won a seat on the Board of Education. He was appointed to the state bench in 1973 for a five-year stint before returning to private practice. He passed away recently at age 93.
Stapleton was at the center of one of the most controversial periods in city history when GOP Mayor Lenny Paoletta, a sometimes adversary, prevailed upon the police board to fire long-time Superintendent of Police and civil servant Joe Walsh in 1983.
Stapleton represented Walsh in his return to duties. The Civil Service Commission reinstated Walsh declaring he was illegally terminated. This set up a confrontation for the ages for control of the police department.
As Stapleton, Walsh and coterie of supporters marched the short walk from City Hall on Lyon Terrace to the police department, Paoletta ordered hulking police officers to bar Walsh from entering the elevator leading to his office.
Fingers pressed holstered guns everywhere.
Stapleton waived the Civil Service order to no avail.
“Joe,” said the mayor. ,
“It’s Superintendent to you,” Walsh shouted back.
“I’m in charge of this department. I’m ordering you not to return
to this office. Police officers will intervene.”
Stapleton prevailed upon Walsh to fight another day. See you in court.
Paoletta issued an executive order declaring his control over the police department and Walsh’s banishment from the building. The mayor immediately appointed Thomas Thear, a former Police Chief of Battle Creek, Michigan, to take charge.
After months of wrangling a state judge reinstated Walsh, ruling there was no just cause for removal. Paoletta leveraged every ounce of his charter-control authority over the police department. He relegated Walsh to a small, first-floor office and appointed officers who had challenged Walsh for years to become de facto heads of the police department.
This maelstrom played out intensely into the 1985 mayoral election when Democrat Tom Bucci defeated Paoletta who had served two terms.
Stapleton’s obituary:
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
