John “Jack” O’Leary passed away on June 10, 2025 at the age of 93. Jack’s legacy of patience, kindness, and resilience will live on in all of the lives he touched. Above all, he treasured his family, and his friendships.
Jack, the oldest of 5 siblings, grew up in Dorchester, son of Mary (Cronin) and John O’Leary of Ireland. He graduated from Boston College High School, Boston College, and received a law degree from Suffolk University. Jack started his career as a math teacher at the Boston Latin School. Upon earning his law degree, he established the law firm of O’Leary, Tierney, and Silverman. In addition, Jack served as the attorney for the Boston Police Relief Association for 50 years. He ended his career working as an attorney in the Suffolk County Registry of Deeds.
Jack was an avid gardener, especially proud of his tomatoes, and enjoyed summering at his home in Parkwood Beach, Wareham. Jack was a huge Boston sports fan, holding season tickets for the Red Sox, Bruins, and Celtics. As a member of the Ancient and Honorable Artillery Company of Massachusetts, Jack enjoyed travelling the world on their tour of duty every Autumn. Jack was a connoisseur of fine dining, especially enjoying the pleasure of shrimp scampi at the Galway House in Jamaica Plain.
He leaves behind his devoted wife, Jane (Cass), of 42 years; his children Karen Granahan (Michael) from Hanover, Susan Haidul (Joseph) from Hanover, Tish (Jack) from Randolph, John (Terri) from Marshfield, and Joannie (pre-deceased) of Quincy, along with 9 grandchildren and 6 great-grandchildren. He is also survived by siblings Kay (Sister Catherine O’Leary SC), Pauline (Jack), and Paul (Marge), and pre-deceased by Frances.
Relatives and friends are invited to visit at the William J. Gormley Funeral Home, 2055 Centre St. West Roxbury on Friday, June 13 from 3-7pm. Funeral from the funeral home on Saturday, June 14 at 9am followed by a Mass of Christian Burial at Holy Name Church, 1689 Centre St. West Roxbury at 10am. Interment to follow at the Blue Hill Cemetery in Braintree.
In lieu of flowers, donations may be made to the Jimmy Fund at Dana-Farber Cancer Institute, PO Box 849168, Boston, MA 02284-9168. For guestbook gormleyfuneral.com.