Harold Alfond Foundation

Harold Alfond Foundation

Harold Alfond established the foundation in 1950 after building Dexter Shoe Company into a national footwear manufacturer. The family sold the business to Berkshire Hathaway in 1993, converting the proceeds into a permanent endowment now valued at $1.428 billion. Successive generations, including sons Theodore B. Alfond and William L. Alfond, serve as trustees and maintain oversight through Dexter Enterprises LLC. The foundation allocates across public equities, private equity strategies, real assets, and direct real estate. Confirmed holdings include Class A and Class B shares of Berkshire Hathaway valued at over $330 million as of 2023 filings, limited partnership interests in Fenway Sports Group, and multiple Maine properties such as Two Monument Square in Portland and the Alfond Youth and Community Center in Waterville. Geographic focus remains inside Maine with secondary exposure through national managers. Ticket sizes range from $5 million to $240 million, with investment horizons of ten to twenty years. Dexter Enterprises LLC acts as the primary investment advisor under Gregory W. Powell, who also serves as foundation chairman. The organization maintains no additional offices outside Portland. In October 2024 the foundation participated in the New England Board of Higher Education Excellence Awards. Related family vehicles include the Alfond Scholarship Foundation, which administers $500 grants to every Maine newborn, and the Peter Alfond Foundation. The foundation operates through a single-family holding company structure that integrates investment management, real-asset ownership, and grant administration under one board. This architecture allows direct control over capital deployment and project execution without external fund commitments or third-party managers for core Maine initiatives.