Robert E. O'Toole, 89, a longtime resident of Milton, died peacefully after a brief illness on May 31, 2026. Born in 1937 and raised in Dorchester as the youngest of eleven children in a traditional Irish family, he grew up with the storytelling gift, quick humor, and warmth that would define him throughout his life. His Irish heritage was a lifelong source of pride, evident in his sharp wit, his tireless work ethic, and his devotion to family. He was brother to the late Sister Katherine O'Toole, Francis O'Toole, Coleman O'Toole, Mary Grant, Anna Daly, Thomas O'Toole, Joseph O'Toole, John O'Toole, Eileen Bassett, and Doris Holmes.

Robert is survived by his beloved wife, Frances Rita (Doherty) O'Toole, with whom he shared more than fifty years of marriage, having celebrated their golden anniversary last June. He is also survived by their son, Christian O'Toole, and three grandchildren, Owen, Callum, and Rory O'Toole of Brooklyn, New York. He was the loving father of the late Coleman Sean O'Toole, who was diagnosed with multiple sclerosis at age sixteen and lived at home for many years thereafter, cared for by his parents until his death in 2018 at age 42. Robert is also survived by many nieces and nephews, and by his in-laws Claire (Doherty) Stanton, Lois Doherty, Carol Doherty, and Paul Doherty.

Robert was a proud graduate of Suffolk University, Suffolk University Law School, and Harvard Law School, where he earned an LL.M. (Master of Laws). As a Professor of Law at New England School of Law specializing in constitutional law, he devoted his career to passionately teaching generations of future lawyers.

When Robert joined the faculty in 1967, the school was known as Portia Law School, reflecting its roots as the nation's law school exclusively for women. Across thirty-six years of service to the institution, he became a revered teacher, noted for his clear presentation, his engaging classroom style, and his infectious sense of humor, and he guided generations of students who went on to successful careers throughout the bar and bench. He was a captivating storyteller who could hold a room with the facts of a complex United States Supreme Court case, then distill the Court's reasoning into the doctrines and rules of law his students could grasp and apply. His courses included agency, alternative dispute resolution, conflict of laws, constitutional law, criminal law, criminal procedure, and equity. A First Amendment scholar, he also taught seminars in choice of law, church and state, the First Amendment, and mass media law.

He served as Dean of the law school from 1971 to 1974. During his tenure, New England received full accreditation from the American Bar Association, and he took great pride in his instrumental role in that achievement. In 1974, New England School of Law awarded him an honorary degree. After earning his LL.M. from Harvard in 1975, he resumed his teaching career with his characteristic passion and commitment, continuing to shape the lives of his students for decades.

At Robert's request, his funeral will be private. Expressions of sympathy may be sent to Frances O'Toole at 151 Monroe Road, Quincy, MA 02169. In lieu of flowers, the family requests that memorial contributions be made to the National Multiple Sclerosis Society through a memorial fund at https://donate.nationalmssociety.org/campaigns/Robert-E--O-Toole