John K. O’Leary, age 75, died peacefully after a courageous battle with cancer. Jack was the loving son of the late William J. (Jack) and Winifred (Bouchard) O’Leary. He was born in Boston and grew up in Braintree. He attended Braintree High School and was a graduate of Newman Preparatory School Class of 1964. After working briefly on the old Boston Fish Pier, Jack entered the United States Army during the Vietnam era. Proud of his military service, he was stationed at Fort Belvoir, VA for its duration, as an instructor for new recruits, in hydraulic missile systems.
On Dec. 4, 1967 Jack and a friend from base were visiting the George Washington Monument in Washington, DC, and there he met his future wife of 51 years, Eileen Kraus. The two began exchanging letters and a courtship began, they married on May 31, 1969 and settled in Wollaston, Massachusetts. Jack and Eileen lived and raised their two daughters in Quincy, Rockland, Norfolk and Brockton, before moving to East Bridgewater and later Bridgewater.
Jack owned Route One Towing, an auto repair and towing company for over 10 years and did rescue and recovery towing for the Mass. State Police. He later worked as a machinist at Northrup Grumman Corp. in Norwood before beginning a successful real estate career. He was vice president and a founding member of the National REO Brokers Association (NRBA) where he worked with membership. He loved people and always helped friends and colleagues when the opportunity arose. It is fair to say Jack was beloved by many in NRBA. Jack loved talking, telling a quick joke or a funny story, and had a knack for always making others feel at ease. As his sister-in-law Nancy Kraus once said, “Jack would be comfortable having afternoon tea with God”. He was an ardent NASCAR fan and on his 50th birthday he completed the Skip Barber Racing School and always fondly told stories about his 442 and his silver-blue Corvette. Whether it was out of state motorists stranded on the highway that he took home to stay with his family while their cars were repaired, homeowners in dire straits needing real estate advice, or NRBA members seeking his opinion on particularly thorny business issues, Jack was always willing to give of his time and expertise, to be of any help to all that he could.
Jack loved being with his granddaughters and great grandsons, and often could be seen giving his great grandsons rides on his lawn tractor or watching trains on YouTube. Jack was the loving husband of Eileen K. O’Leary of Bridgewater and devoted father of Maureen E. DeRito and her husband Timothy of Pembroke and Janice H. Dwyer of Bridgewater. Loving “Papa” of Lenna P. Zitter and her husband Andrew of MD, Christina J. DeRito and her fiancé Mat of VA, Lorianna M. Dwyer and her fiancé Dan of Brockton , Allison A. DeRito of Pembroke, and “Great Papa” of Philip and Timothy Zitter. Brother of Catherine McLaughlin of N. Quincy, Patricia Reppucci of Brockton, Susan O’Leary of Braintree, and the late James T. O’Leary.
Family and friends are cordially invited to the Prophett-Chapman, Cole & Gleason Funeral Home, 98 Bedford St. Bridgewater on Thursday Nov. 19th for a visitation period from 4-8 pm. (Please wear a mask and socially distance). A private funeral Mass for family will be celebrated at Stonehill College on Friday.
In lieu of flowers, donations may be made to the Jack & Eileen O’Leary Scholarship Fund, c/o Stonehill College, Advancement Office, 320 Washington Street, Easton, MA 02357.