John "Jack" Regan, of Newport, Rhode Island, passed away peacefully on May 21 with his family by his side. Born on Christmas Day in 1940 in Waltham, MA, Jack never missed an opportunity to remind people he was "the second coming." He was raised in Newton, MA, to Irish immigrants, Timothy and Katherine (King) Regan.

Jack met his wife of 60 years, Virginia "Ginny" McGinn, of Newport, while living in Boston. Together they built their life in Waltham, where they raised their family while spending summers in Newport and Cape Cod.

Jack proudly served his country as a member of the United States Marine Corps Reserve. He went on to earn both his bachelor's degree and his master's degree from Suffolk University and later enrolled in Boston College's Education Leadership doctoral program to become certified as a superintendent.

Jack began his career at Waltham High School as a mathematics teacher, later advancing to Housemaster, and ultimately serving as Principal - a position he held for many years. He also had a passion for football, coaching at Waltham High School before going on to serve as Assistant Coach and then Head Football Coach at Bentley University in Waltham.

After his tenure at Waltham High School, Jack and Ginny returned to Newport, RI, where Jack served as principal of Middletown High School for many years. After retiring from public school administration, he became principal of Cluny School in Newport and, even after retiring (again!), returned to education as principal of St. Pius School on Cape Cod. His enduring commitment to students and their schools earned him the affectionate nickname "the Brett Favre of principals."

A man of strong faith, Jack served as a Eucharistic minister at St. Mary's Catholic Church in Newport. He was a longtime member of Wanumetonomy Golf & Country Club and Hazard's Beach. His early childhood summers in Green Harbor in Marshfield, MA, and family memories in Brewster, Cape Cod, remained close to his heart.

Jack especially loved walking his dogs, with a parade of loyal yellow labs (several from Lucky Lab Rescue) by his side over the years. He was an avid golfer and Boston sports (and later Friars) enthusiast.

He is survived by his wife, Virginia McGinn Regan of Newport; his son, John Regan and his wife Naomi of Seattle, WA; his daughter, Christine Fleming, and her husband, William, of Hanover, MA; his grandchildren, Jack and Amanda Fleming of Hanover; and many nieces and nephews.

He was predeceased by his son, Rhode Island State Trooper Timothy Regan and his sisters: Bernadette Kelly, Nancy A.M. Spinney, Patricia Hirtle, and Maureen Heavey.

Family and friends are invited to attend a Mass of Christian Burial at St. Mary's Catholic Church in Newport on Tuesday, May 26, 2026, at 10 a.m.

Burial will immediately follow at St. Columba Catholic Cemetery, 465 Brown's Ln., Middletown

In lieu of flowers, donations in Jack's memory may be made to the Timothy Regan Memorial Scholarship Fund, c/o Waltham High School, 617 Lexington Street, Waltham, MA 02452.

In Jack's memory, the family invites you to raise a glass of Drambuie, enjoy a singalong to "Danny Boy," or share a pint in his honor-in celebration of a life well lived. Sláinte.