Kathleen May Flagg Connolly

1944 - 2024

Kathleen May Flagg Connolly
Kathleen May Flagg Connolly passed away suddenly in Richmond, VA on May 7th doing what she loved best, spending time with a grandson at his university. Kathy was born in Cambridge, Massachusetts on May 29, 1944, to Charles and Evelyn (Brown) Flagg.
Kathy graduated from Cambridge High and Latin School. She worked for John Hancock Insurance Company in Boston as a Key Punch Supervisor. She also worked at the Perrot Memorial Library, in Greenwich, which she thoroughly enjoyed, not just for her co-workers but also the books. Kathy loved to read – mysteries were her favorite. Later, she and husband Tom, whom she married on October 21, 1966, formed Thundercloud Consulting Group supporting universities in the Boston area.
Kathy also loved to travel. She and Tom visited all 48 states on the continent. Together they roamed Europe in a series of trips. Her favorite city: Venice. Her favorite city in the US: every one. Kathy was a loyal American and believed deeply in the Constitution and the freedoms it promised.
In her 80 years of life Kathy got her strength from her 58-year marriage to Tom and their family. In addition to her husband, Kathy is survived by her son Thomas, his wife Anastasia and their two children Alaine and Aidan; and her son Robert, his former wife, Maureen Geraghty and their son Gavin. Kathy is also survived by her brother Aubrey Flagg and his wife Judy. Kathy was predeceased by four siblings: Beverly Harkins, Merton, Judy Colon and Denise Simpkins. Kathy is also survived by many beautiful nieces and nephews.
A funeral Mass will be held to celebrate her life at St. Leo Church, 24 Roxbury Rd., Stamford, CT on June 8th at 2 p.m. In lieu of flowers, contributions may be made to the Catherine Connolly Schmitt Memorial Scholarship Fund at Laboure College of Healthcare, 303 Adams St., Milton, MA 02186.