Rob begins his first term as a trustee after having served on the Board in a pro-tem capacity for six years as the president of the Middlesex Alumni Association. He is a partner of Fagan & Boshart Wealth Management, a nationally recognized wealth management team at J.P. Morgan. Prior to joining J.P. Morgan, he spent 15 years at State Street Global Advisors (SSGA), where he was a managing director and head of Americas institutional ETF sales. While at SSGA, Rob was also a member of the senior leadership team, helping to shape and execute corporate strategy.

Rob’s Middlesex legacy originates with his great-great-grandfather Robert Winsor, older brother of founder Frederick Winsor and longtime trustee and supporter of the School. Alumni in Rob’s family thereby include his great-grandfather, the late Walter H. Trumbull ’11, his grandfather, the late Philip W. Trumbull ’38; his father, Philip W. Trumbull, Jr. ’67; and his sister, Amy C. Trumbull ’96.

Rob holds an M.B.A. from Babson College and a B.A. from Rollins College. He also serves as vice chair of the Board of Overseers at the New England Aquarium and as Commissioner of Trust Funds in Weston, Massachusetts.