Theodorick (Todd) B. Bland joined Milton Academy as its 12th head of school in 2009. Since his arrival, he has engaged the Milton community in celebration of the school’s strengths and in planning for bold, inspiring educational leadership for the future.

Throughout Bland’s tenure at Milton, the school completed its Dare campaign—the most ambitious and successful capital campaign in its history. The campaign raised $48 million for student financial aid, including the establishment of 44 new scholarship funds; supported an increase to faculty salaries and a more robust professional development program; and upgraded academic and residential spaces across campus. Under Bland’s leadership, Milton implemented an institution-wide strategic plan to maintain and nurture the best and strongest faculty; has consistently and rigorously renewed curriculum; and has continued to enroll a diverse, multi-dimensional student body. Recently, the school adopted a new diversity, equity, inclusion, and justice strategic plan and vision to ensure that every member of the community knows and feels that they belong at Milton.

Since 2009, Milton has built and opened the Pritzker Science Center, providing state-of-the-art science classroom and laboratory facilities; redesigned and enhanced the Arts and Media Center, responding to evolving student interests and improving spaces for computer science, robotics, and visual arts; built the Berylson turf field; renovated and added residential spaces for students and faculty; and modernized Ware Hall. Projects are underway for the completion of the Cox Library relocation to Wigglesworth Hall in 2023 and a new home for math in 2024.

Each year, Bland teaches every grade in the school (K–12). In addition to being one of the most enjoyable parts of his role, this classroom time allows him the opportunity to build relationships with students as both an educator and the head of school.

Bland has had an extensive career in independent education—teaching, coaching, and serving in administrative leadership positions. He began at Belmont Hill School, teaching history and coaching. He taught Spanish and coached the following year at Beaver Country Day School, before returning to Belmont Hill where he assumed a number of different roles. For eight years, he taught history in grades 7 through 10, advised ninth grade students, and coached varsity lacrosse. As an administrator, he oversaw admissions, financial aid, and public relations. From 2001 to 2009, Bland worked at the Seven Hills School, a K–12 school in Cincinnati, Ohio, first serving as assistant head of school, then as upper school principal and later as interim head of school.

Bland was born in Boston and grew up in Brunswick, Maine; Washington, DC; and San Francisco. He attended St. George’s School where he was prefect, a three-sport varsity athlete, and lacrosse All-American. He graduated from Bowdoin College with a double major in history and Spanish and a minor in government and legal studies, and was a four-year letterman in lacrosse, captain, and MVP. He earned his master’s degree in education with a focus on administration, planning, and social policy from the Harvard Graduate School of Education.

His ties to Milton extend back decades: Bland’s parents both graduated from Milton in 1958. His father, James, was a professor of colonial American history at Bowdoin; his mother, Sherrell, was a teacher of United States history in Massachusetts public schools. Bland’s father died when he was a child, and is memorialized in Milton’s Apthorp Chapel.

Outside of Milton, Bland has held a number of board positions, including for the the Epiphany School in Dorchester; the Steppingstone Foundation, a program that prepares Boston students for education opportunities that lead to college success; and as head of the board for the National Network of Schools in Partnership, an organization that fosters collaboration across public and private schools. Bland in 2011 was elected into the Headmaster’s Association, an organization that brings together heads of independent schools and public school superintendents across the United States. In 2021, Bland led a team of visiting educators for Phillips Academy Andover’s reaccreditation with the New England Association of Schools and Colleges.

Bland lives on campus with his wife, Nancy Frost Bland, a lifelong educator who has worked in Milton’s Office of Admission and served the school as an advisor and substitute teacher. The Blands have three children: Nick ’13, Maggie ’14 and Emily ’14; a daughter-in-law, Philly Bland, and a grandson, James Bland.