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Harold Alfond

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Adapted from the English Wikipedia article Harold Alfond, available under CC BY-SA 4.0Updated 11 August 2025
Harold Alfond
Born (1914-03-06) 6 March 1914 (age 112)
Swampscott, Massachusetts, U.S.
Died16 November 2007(2007-11-16) (aged 93)
Belgrade, Maine, U.S.
Occupation(s)Entrepreneur, philanthropist
Known forFounder of Dexter Shoe Company; pioneer of factory outlet stores; minority owner of the Boston Red Sox

Harold Alfond (March 6, 1914 – November 16, 2007) was an American entrepreneur best known for founding the Dexter Shoe Company, pioneering the concept of the factory outlet store, and holding a minority stake in the Boston Red Sox.

Early life

Alfond was born in Swampscott, Massachusetts to Simon and Rose Alfond, immigrants from Russia. Raised alongside his siblings in Swampscott, he cultivated a strong enthusiasm for athletics during his high school years.

Founding Dexter Shoes

Following his graduation in 1934, Alfond began his career at Kesslen Shoe Company located in Kennebunk, Maine, where he swiftly advanced to the position of factory superintendent. In 1940, together with his father, he acquired a shoe manufacturing facility in Norridgewock, Maine, establishing the Norrwock Shoe Company. They sold this enterprise for $1 million in 1944, with Simon Alfond continuing as president for a quarter-century.

In 1958, Harold acquired a woolen mill situated in Dexter, Maine and launched the Dexter Shoe Company. The firm initially focused on producing private label footwear for major retailers such as Sears, JC Penney, and Montgomery Ward & Co., before developing its own Dexter brand distributed through independent shoe retailers nationwide.

Alfond was instrumental in introducing the factory outlet store model by inaugurating a retail location at Dexter’s manufacturing plant in 1971. This initiative involved direct sales of factory seconds and excess inventory to consumers, which eventually expanded into a network exceeding 80 outlet stores by the 1990s. During this expansion, Dexter shifted from operating standalone rustic-style outlets to leasing spaces within outlet malls.

Throughout the 1970s and 1980s, Dexter experienced significant growth amid rising interest from national retail chains eager to expand through overseas production. In 1993, Alfond sold Dexter along with affiliated companies Pan Am Shoe and Ocsap Ltd. to Berkshire Hathaway for $433 million in stock while maintaining family management oversight. Eight years later, Warren Buffett merged Dexter into H.H. Brown and later described the acquisition as "the worst deal that I've made." Alfond continued serving as President of Dexter until its integration with H.H. Brown.

Philanthropy

To organize his charitable activities, Alfond founded Maine’s first private foundation, the Harold Alfond Foundation. Between 1950 and 2003, it donated over $100 million to various initiatives and held assets exceeding $106 million by 2008.

Alfond supported numerous educational institutions by enhancing their athletic and academic infrastructure. Significant contributions include the Alfond Arena and Alfond Stadium at the University of Maine; the Harold and Ted Alfond Sports Center at Rollins College; the Harold Alfond Center for Health Sciences and Alfond Forum at the University of New England; the Harold Alfond Management Center at UMass Amherst's Isenberg School; and the Alfond Center at Saint Joseph's College of Maine. In recognition of his impact, the University of Maine unveiled a bronze statue honoring him in 1999. Additionally, he donated $1 million toward St. Joseph's College’s $10 million Alfond Hall project in 2003.

In 2020, Colby College completed a 350,000-square-foot Harold Alfond Athletics and Recreation Center, largely funded by an $80 million lead gift from the Harold Alfond Foundation.

The Foundation has also been a key benefactor of Kents Hill School in Readfield, Maine, financing projects such as the Alfond Athletics Center (2001), New England’s largest turf complex (2008), a $2.3 million endowment for the Akin Learning Center (2011), and a $3.5 million matching grant toward a new dining facility (2015).

After battling cancer for 17 years, Alfond contributed $7 million in 2007 to establish the Harold Alfond Center for Cancer Care at MaineGeneral Medical Center.

In 2009, the Alfond Scholarship Foundation initiated the "Harold Alfond College Challenge," which provides a $500 grant to every child born in Maine before their first birthday to encourage future higher education savings. As of December 2024, this program alongside its partners has invested over half a billion dollars since its inception in 2013, benefiting more than 164,000 children across Maine.

Investments in sports

In addition to contributing funds for collegiate athletic facilities, Alfond took an active role in sports-related investments. In 1978, he became a limited partner of the Boston Red Sox after a consortium sought a Maine-based sports enthusiast to join their ownership group. Following the 1993 sale of Dexter to Berkshire Hathaway, the Alfond family maintained their ownership interest, which is now managed by two of his sons.

During the 1980s, Alfond supported sailor Kevin Mahaney in his Olympic pursuits; Mahaney went on to secure a silver medal at the 1992 Summer Olympics.

Alfond was also a co-investor in the Belgrade Lakes Golf Club, located near his summer residence. This facility is regarded as one of the premier public golf courses nationwide. In 2002, Golf Digest honored it as the sole five-star public course in the Northeast.

Family life

In 1943, Alfond married Dorothy Levine; together they had four children—Ted, Susan, Bill, and Peter—and thirteen grandchildren. Dorothy passed away in December 2005.

One of their grandsons, Justin Alfond, pursued a political career, winning election to the Maine Senate in 2008 and serving as Senate President in 2012.

Death

Alfond passed away from prostate cancer on November 16, 2007, in Belgrade, Maine.