Thomas W. McGillicuddy, Fairfield Prep's First Lay Principal, Dies At 83

FAIRFIELD, Conn. — Thomas W. McGillicuddy, a longtime teacher and administrator at Fairfield College Preparatory School, passed away peacefully Jan. 4 at Bridgeport Hospital with his family by his side. He was 83.

Thomas McGillicuddy
Thomas McGillicuddy Photo Credit: Lesko Polke Funeral Home

Born in Worcester, Mass., on May 6, 1934, McGillicuddy graduated from The College of the Holy Cross before beginning his more than 42-year career at Fairfield Prep. Joining the Prep community as a math teacher, McGillicuddy went on to serve as dean of men, principal, guidance, dean of discipline and college placement counselor and controller.

“Known to be tough but fair, he was respected by the boys at Prep and they knew they could count on him for assistance,” according to an e-mail sent to the Prep community. “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.”

McGillicuddy’s connections to Prep ran deep. He was the father of Stephen T. McGillicuddy '77 and Brian P. McGillicuddy '81, grandfather of Michael P. McGillicuddy '09, and Max T. McGillicuddy '20 and father-in-law of Timothy J. Foley ’81.

He was married for more than 59 years to the love of his life, Joan Costello McGillicuddy. They were Fairfield residents for more than 45 years.

In addition to his wife, he leaves behind his son Steve of Fairfield; daughter Patty McGillicuddy Foley and her husband Tim of Trumbull; his son Brian and his wife Celeste of Trumbull; his daughter Cathy and her wife Marikate Murren of Enfield; and a sister Marie Coyle of Worcester.

He was predeceased by his mother and father, Agnes and Tom McGillicuddy; and his sister, Kaye Pendergast and his brother, John McGillicuddy.

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: Kathleen McGillicuddy Regula and her husband Matt of Fairfield; Michael McGillicuddy 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 and Callie McGillicuddy, all of Trumbull.

He also had the opportunity to meet and love four great-grandchildren: Madison, Riley and Peyton Regula and Ryan Tobitsch.

Calling hours will take place from 4 to 8 p.m. Friday at the Lesko & Polke Funeral Home, 1209 Post Road, Fairfield. A Mass of Christian Burial will be celebrated at 11 a.m. Saturday at the Fairfield University Egan Chapel of St. Ignatius Loyola.

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, memorial donations may be made to Fairfield Preparatory School, 1073 N. Benson Road, c/o Thomas McGillicuddy Scholarship Fund to afford a deserving young man the opportunity to attend Fairfield Prep.

For directions, to order flowers or to sign his online guest register, visit

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