Writing about Gerry Ragland will be a pleasure for me, for I have known Gerry since 1996 when I competed against him in the inaugural Old Town Crier Cup sailboat race…and it is the only time I ever beat him. I will address the race a little later.

The 73-year-old Ragland has strong ties to his native Alexandria. He was born at Duke and Washington Streets. His dad ran a garage on Route 1 and Old Mt. Vernon Highway, not far from Alexandria. When America entered World War II, Mr. Ragland senior moved to Baltimore to work at the shipyards. A little later Mr. Ragland, Sr. enlisted in the Marine Corp and saw action at Iwo Jima. While his dad was overseas, Gerry and his mom, Edith Drumheller, moved back to her native Rockfish, Virginia in Nelson County. There is a little bit a history here, as Edith had attended Schuyler High School and graduated Salutatorian while Earl Hamner Jr. graduated Valedictorian. Hamner wrote several semi-autobiographical stories about his experiences there while growing up during the Great Depression, including Spencer’s Mountain which was made into a movie in 1963. Hamner also wrote the Homecoming, which was the catalyst for the CBS television series, The Waltons. Edith’s dedication to school had a profound effect on Gerry and he became the first in his family to go to college.

After the war, the family moved to the town of Crewe in Nottoway County, Virginia, where Gerry put himself through college working as a brakeman in the local train yard. His education was interrupted for a year when he dropped out of Lynchburg College, but later began attending Longwood College in Farmville, Virginia, which today is Longwood University. During this time period, Gerry also taught drama at Falls Church high school and later attended Temple University to receive his law degree. He attended night school for 4 years while working for the Philadelphia Housing Authority.

Upon graduating, Gerry opened up his own law practice and practiced law in Philly for the next ten years. In 1981, after receiving his first big settlement, he bought himself a 27-foot Tartan sailboat. His love for sailing had been cultivated years before when he and some friends would venture to Baltimore and charter sailboats.

In 1987, Gerry moved to Old Town Alexandria, Virginia and rented a slip in Annapolis for his beloved sailboat. A few years later he bought a condo on Back Creek in Annapolis with a slip and moved his boat there. Today, Gerry has a Tartan 34.2 and tries to get out sailing as often as possible; however, even at 73 years he is still practicing law with the firm of LeClair Ryan.

When I asked what type of law, his response was “Professional Liability Defense work.” His focus includes serious personal injury, wrongful death, healthcare litigation, medical malpractice and business litigation. For the last twelve years Gerry has represented clients in numerous cases involving nursing homes. These cases have addressed issues such as pressure sores, falls, medication errors and sexual abuse.

Gerry also took up photography in the 1970’s. He would shoot with his Yashica-Mat double lens reflex and then develop his own film. In the 1990’s he took some photography classes and today with his Nikon digital camera, he is an accomplished photographer.

Now, about that sailboat race. In 1996 we launched the first Old Town Crier Cup Race, which was a race between 6 33-foot Hunters that were provided by Sunsail Yacht Charters of Annapolis. The race was from Annapolis to St. Michaels, Maryland. With very little wind that day we had to shorten the race and right at the last mile, in a very light breeze, I passed Gerry’s boat. We continued the Old Town Crier Cup for another 9 years but sailing around buoys in our own boats in Solomon’s Maryland. I could come close, but I never beat him again. A true renaissance man for the times, Gerald Ragland, Jr. just keeps going, and going, and going…

Written by: Bob Tagert