Rob Simpson’s Bequest to the William Ireland ’65 Memorial Scholarship

Dr. Robert E. Simpson, Jr. ’65 grew up on a peach farm in nearby Southington, Connecticut, in a middle-class family and received a scholarship to attend The Choate School. His brother, Mark ’66, is also an alumnus. Rob says the most important things he gained from his Choate experience were lifelong values rooted in education and friendships.

To ensure that future students have access to the same opportunities, Rob has arranged a bequest in his will to support the William Ireland ’65 Memorial Scholarship. Established in 1971 to honor a classmate who died unexpectedly, the scholarship was one of Choate’s first designated to support students of color and continues to benefit multiple students each year.

At Choate, Rob played football, hockey, and lacrosse and was on the News Board, Glee Club, and St. Andrews Cabinet. He went on to graduate from Amherst College, Simmons University, Harvard School of Public Health, and the University of Utah. Rob worked as a psychiatric hospital CEO and now as a consultant on leadership for physicians and executives in healthcare and advocates at the state and federal levels for mental health parity. Rob is a recipient of the American Hospital Association Grassroots Champion award.

Rob has remained deeply connected to Choate Rosemary Hall. He is considered one of the unofficial leaders of the Class of 1965, which received the 2025 Distinguished Service Award for its remarkable bond, service, and philanthropy, particularly related to the Ireland ’65 Fund.