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Gerald “Jerry” File has carried a commitment to service from Alexandria’s Del Ray neighborhood to the Marine Corps and back home again, where he has spent decades supporting young people, veterans and some of the city’s best-known civic institutions.

His selection as a 2025 Living Legend holds special meaning for the Alexandria native.

“This Award is particularly memorable for a boy who grew up in Del Ray and received a public school education,” File said.

File credits his mother with instilling the charitable spirit that would shape his life. When he began receiving a weekly 50-cent allowance at age 8 or 9, she told him to put 10 cents in the collection basket each Sunday at St. Rita’s Catholic Church.

He soon began helping the director of the fledgling Del Ray Boys Club raise money—an early introduction to the fundraising and volunteer work that would become central to his civic career.

Sports were another major influence. File competed in Alexandria youth athletics, attended George Washington High School and earned a football scholarship to the College of William & Mary. After graduating in 1961, he joined the United States Marine Corps.

File finished first in his class at the U.S. Army Intelligence School and reached the rank of major in eight years, about four years faster than was typical. His decorations recognized service during the 1962 Cuban Missile Blockade and combat operations in Vietnam, including Khe Sanh in 1967, when he was a captain.

He later recruited officers from diverse backgrounds and embraced the Marine Corps expression “Gung Ho,” meaning “work together.” His decision to leave military service was driven by his responsibilities at home. With promotions slowing and two young children, he was concerned about paying for their college education.

Returning to Alexandria in 1970, File entered the investment business and turned his military recruiting experience into a memorable sales pitch.

“I was successful at getting young men to go to Vietnam,” he recalled telling a manager. “Certainly I’ll be successful getting people to invest money with me, right? Nobody’s shooting at them.”

File went on to become a founding partner of Winthrop Financial Company, which grew into the country’s largest private real estate investment bank. He said the company raised more money than prominent firms including Merrill Lynch and E.F. Hutton.

Decades Devoted to Alexandria’s Youth

File brought the same drive to community service. Guided by a principle he attributes to Ronald Reagan—that the country needs more volunteer community leaders rather than more government—he became deeply involved with organizations serving young people.

He has spent 35 years as a president and board member of the Boys & Girls Clubs. During that time, he advocated for adding “Girls” to the organization’s official name, helped deliver three consecutive balanced budgets and worked to strengthen its long-term finances.

File also used his investment-industry connections to raise more than $1 million apiece for the Boys & Girls Clubs of Greater Washington, Gonzaga College High School and the Washington Jesuit Academy.

His approach to fundraising rests on a straightforward belief in each organization’s mission. As he put it, “How could you not contribute to the Boys & Girls Club?”

The Alexandria Sportsman’s Club has received 40 years of File’s time. He has served as its president and fundraiser, supporting an organization founded in 1947 to recognize high school athletes and provide college scholarships. The club honored him with its William Hershberger Civic Award at its 1998 awards banquet.

File and his late wife, Debbie, were also founding supporters of the Washington Jesuit Academy, which has spent the past 25 years educating boys considered at risk.

After Debbie died of cancer, File donated $50,000 in 2021 to a new student health clinic at Bishop Ireton High School. The clinic was named in memory of Debbie, who had volunteered as a nurse in local schools.

Continuing to Serve Alexandria’s Veterans

File has remained equally committed to fellow veterans. In August, the decorated Vietnam veteran raised $10,000 for the Alexandria Vietnam War Memorial. He also founded the Marine Corps Birthday Celebration at the Old Dominion Boat Club, an event that has continued for 32 years.

Sharon “Teddy” McBay, File’s partner, said he “has significantly enhanced the quality of life in Alexandria and serves as an inspiration to many others.”

McBay and File first met as William & Mary undergraduates. McBay shared a dormitory room with Sarah Kemp, later Sarah Brady, and the two women and their future husbands developed an enduring friendship. Sarah’s husband, James Brady, became White House press secretary and was seriously wounded in the March 30, 1981, assassination attempt against President Ronald Reagan.

Even File’s favorite-restaurant list reflects his attachment to Alexandria. Calling the question the toughest he had been asked, he settled on a tie between Ralph Davis’ Mystic BBQ and Hossein Pishdad’s The Warehouse, praising their food, service, management and Old Town locations.

Now retired and living at Goodwin House, File remains active. He recently finished a biography of former Defense Secretary James Mattis and keeps five books on his nightstand. He and Debbie had two children; his family now includes five grandchildren and three great-granddaughters.

For File, the purpose of his long record of service remains rooted in what comes next.

“The young people are our future,” he said. “And I think these groups help these young people become better citizens, which helps our community, helps our state, helps our country.”