Robert J. O’Leary, Sr.

Robert J. O’Leary Sr., 88, a retired Boston Police Sergeant, died peacefully on January 27, 2019.

Born in Mission Hill Roxbury, Mr. O’Leary began his lifelong dedication to service in 1951 when he enlisted in the U.S. Coast Guard. After serving during the Korean War, Mr. O’Leary left to work as a prison guard at the old Charlestown State Prison before joining the Boston Police Department in 1955. Originally stationed at District 9 in Roxbury, he moved to Area C in Dorchester before becoming an inaugural member of the Department’s Crime Prevention Bureau and later the Officer Friendly program.

Mr. O’Leary is probably best remembered, though, for his deep faith, quick humor and kind and loving nature, as well as his service to both his community of Dochester and Parish of St. Mark’s. He is also well known for his work for two international missions, organizing a community-based effort to collect and redeem discarded cans to raise thousands for the charities in Brazil and Haiti.

Mr. O’Leary was predeceased by his wives Patricia (Donoghue), Margaret (Sheehan) and Virginia (Doherty); sisters Eleanor Cronin, Marie O’Leary, Jeanette O’Leary, Virginia Redfern; and brother Francis. He is survived by his sons Robert J. Jr. of Weymouth and Richard of Boulder, CO; daughters Eileen Konik of Westford and Karen Theroux of Nantucket; sisters Constance Conroy of Pembroke and Gertrude Triller of Proctor, VT; eight grandchildren and many nieces and nephews.

Relatives and friends are respectfully invited to attend the visiting hours on Friday 4-8 PM in the McDonald Keohane Funeral Home SOUTH WEYMOUTH at 809 Main Street (Rte 18 opp. So. Shore Hospital). Relatives and friends will gather in the funeral home at 8:45 AM on Saturday prior to the Funeral Mass in Sacred Heart Church, Weymouth at 10 AM. Burial in St. Joseph’s Cemetery, West Roxbury. Mr. O’Leary made sure to let his family know that donations in his memory may be made to The Home for Little Wanderers, 10 Guest St., Boston, MA 02135.