Thomas Walter McGillicuddy

Thomas Walter McGillicuddy, 83, aka Tim, Dad and Pepe passed away peacefully on January 4, 2018, at Bridgeport Hospital with his family by his side. He was born in Worcester, Massachusetts, on May 6, 1934. After graduating from The College of the Holy Cross, Tim began his career at Fairfield Preparatory School where he went on to dedicate over 42 years. Joining the Prep community as a math teacher in 1956, Mr. Thomas " Tim" McGillicuddy, went on to serve the Prep community extremely well in several roles, including Dean of men, Principal, Guidance and College Placement Counselor, and Controller. His most important and memorable role was being named the very first lay Dean of Discipline. Known to be tough but fair, he was respected by the boys at Prep and they knew they could count on him for assistance. He also had the distinction of being the first lay principal in the school's history, a post he held during the 1970s. More importantly, he was a friend, confidant, and mentor to countless students, faculty and alumni of the school. Tim was also incredibly generous and loved sharing his home in Rhode Island with friends and family. Mr. McGillicuddy was incredibly close to his family and extremely proud of his four children. He was married for over 59 years to the love of his life, Joan Costello McGillicuddy. They were Fairfield residents for over 45 years. In addition to his wife, Joan, he leaves behind is son Steve of Fairfield (class of '77), daughter Patty McGillicuddy Foley and her husband Tim('81) of Trumbull, his son Brian ('81} and his wife Celeste of Trumbull and his daughter Cathy and her wife Marikate Murren of Enfield and a sister Marie Coyle of Worcester, MA. He was predeceased by his mother and father, Agnes and Tom McGillicuddy of Worcester, MA, his sister, Kaye Pendergast and his brother, John McGillicuddy, both of Massachusetts Although Fairfield Prep and his family had a special place in his heart, he had a true sparkle in his eye when it came to his grandchildren. Pepe was the name that meant the most to him. He had a special relationship with each one and a bond that will always be there; he will be missed by Kathleen McGillicuddy Regula and her husband Matt of Fairfield, Michael McGillicuddy('09) of Fairfield, Erin Foley Tobitsch and her husband Steve of Trumbull, Christine Foley and her boyfriend Pat Mihai of Brooklyn, Katie Foley of Trumbull, and Madison, Dani, Max (2020) and Callie McGillicuddy all of Trumbull. He also had the opportunity to meet and love four precious great grandchildren: Madison, Riley and Peyton Regula and Ryan Tobitsch. He had a unique relationship with each family member and will be sadly missed. Calling Hours will take place on Friday at the Lesko& Polke Funeral home 1209 Post Road in Fairfield from 4-8 pm and on Saturday at The Fairfield University Egan Chapel for a Mass of Christian Burial at 11:00 am. A shuttle bus will be available from the parking lot. Burial will be immediately following the Mass at Lawncroft Cemetery in Fairfield. In Lieu of flowers donations may be made to Fairfield Preparatory School, 1073 North Benson Road, C/O Thomas McGillcuddy Scholarship Fund to afford a deserving young man the opportunity to attend Fairfield Prep, a place he loved and made a part of his extended family. For directions, to order flowers or to sign his online guest register please visit