Robert Emmett O'Leary “Bob”, a lifelong resident of Charlestown, Massachusetts, passed away peacefully at his home on June 10, 2026. Born on June 8, 1944, Bob lived a full and devoted life marked by dedication, kindness, and a steadfast commitment to both his community and family.

Robert was a retired Assistant Clerk of the Massachusetts Trial Court, having devoted 44 years of exemplary service, culminating in his retirement from the Chelsea District Court. His work was characterized by professionalism and a deep sense of responsibility, earning him the respect and admiration of colleagues and the many individuals who came through the court system. He was also a former member of Local 25 Teamster’s Union.

A late Army veteran, Bob carried the discipline and honor of his military service into every area of his life. With his ever-cheerful and upbeat personality, he was known to brighten the days of those around him. He took great joy in simple pleasures from watching any sports broadcast to his absolute favorite, golf, riding his purple huffy around Charlestown, and swimming laps at the YMCA in the Navy Yard.

Among Bob’s proudest accomplishments was his beloved family. He is survived by his Beloved wife, Donna (O'Halloran) O'Leary; predeceased by his son Kerry Jonathan O’Leary, his daughters Katie O'Leary and Her Husband Billy Spencer and Bonnie O'Leary; cherished grandchildren Sadie, Mia, Christian, Alannah, and Brayden. He was affectionately known as a beloved Dampa, a title he held with immense pride. Robert also leaves behind his brother James "Jimmy" O'Leary and his wife Marie, as well as brothers-in-law Kevin O'Halloran and his wife Laurie, Joseph Scibilia, and sister-in-law Jean O'Halloran, and many nieces and nephews.

Robert was predeceased by his parents, Robert and Phyllis O'Leary; his brother John "Jackie" O'Leary and sister-in-law Kathy O'Leary; his sister Geraldine “Gerry” Scibilia; and brother-in-law John O'Halloran.

Robert’s kindness, his dedication to service, and his unwavering love for his family made an indelible impact on all who knew him. His memory will be treasured deeply by his family, friends, and all who were fortunate to cross his path.

Family and friends are invited to pay their respects during a visitation on Wednesday, June 17, 2026, from 4:00 PM to 7:00 PM in the Carr Funeral Home, 220 Bunker Hill Street, Charlestown. A Mass celebrating Robert’s life will be held on Thursday, June 18, 2026, at 11:00 AM in St. Francis de Sales Church, 313 Bunker Hill Street, Charlestown. Burial will follow at Woodlawn Cemetery, 302 Elm Street, Everett. at 12:30 PM.

Robert Emmett O'Leary’s legacy of warmth, integrity, and dedication will forever remain in the hearts of his family and community. He will be remembered as a man who lived life with cheerful determination and an open heart, leaving behind a world made better by his presence.

In lieu of flowers donations can be made in his name to:

North Suffolk Community Services https://web.charityengine.net/Default.aspx?tsid=28869 

or

Charlestown Boys and Girls Club https://www.bgcb.org/donate/ (Please select Charlestown Boys and Girls Club in "I want to support")