Harold Lee Letterman

Harold "Skip" Lee Letterman, 80, passed away on 21 November 2025, in Williamsburg. Born on May 26, 1945, in Lock Haven, Pennsylvania, Harold spent his early years following WWII, in a vibrant community among the Amish, home to Piper Aviation, situated between the banks of the Susquehanna River and Bald Eagle Mountain.

Before the levies were built, he and his adopted mother Geraldine Caldwell and grandmother Amy Caldwell survived several floods. He grew up with big band music, the juke box, sock hops, drive-ins, and was active in the Boy's youth choir who appeared on a local TV program one Christmas. He loved to dance and that continued throughout his life.

He answered the call to duty at 19 years of age and enlisted in the Army. He married Barbara Bartholomew, shortly thereafter, and volunteered to go to Vietnam from 1965-66, just prior to the birth of his first child, Michele. Although he suffered no physical wounds during the war, he was exposed to Agent Orange and suffered from PTSD until his death.

He served in the Philippines, Okinawa, Ft. Bragg, and 10 years throughout Germany in Frankfurt, Baumholder and Bremerhaven. His second child, Christopher Todd, was born in Frankfurt. Skip went on to become a Warrant Officer and retired after 23 years of active service as Chief Warrant Officer. Although Skip was very proud of his years of service, he was never boastful. He was a staunch patriot and defender of the constitution until his death.

After retiring from active duty, he went on to work as a civilian for the Department of Defense (DOD) for ten years after which he retired and became a defense contractor for both the DOD and Central Intelligence Agency (CIA) until May 2022 when he permanently retired. During his time with DOD, he met and later married his second wife, Virginia "Ginger" Pierson. They had two children together, Eryn Virginia Letterman and Benton Takota Letterman. Skip and Ginger retired in 2022 and relocated from Reston, Virginia to Williamsburg, Virginia with their grandson Aiden Tyler who spends each school year with them. Skip was a loving "Opa" to his grandchildren Aiden, Josh, Meghan, and Trevor and loved race cars, Key West, great beer, anywhere in Italy, Ireland, or Germany, action movies, documentaries on space and ancient ruins, his dogs and cats, Christmas, and his family.

Skip suffered from a stroke and heart attack combined shortly after their move to Williamsburg but, being a tough soldier, Skip defied the odds and made a full recovery. Skip had just reached his three-year anniversary since his illness and was looking forward to the holiday season ahead when he passed. He spent a quiet evening with his wife and grandson, watching the original Grinch movie. He kissed his family goodnight, then went onto the bed and slipped quietly away, no pain or anguish. He had a big heart and sense of humor to match. He was our North star and will be greatly missed.

Skip is survived by his first wife, Barbara Bartholomew; daughter, Michele (Letterman) McBride and grandson, Joshua McBride of Lock Haven, Pennsylvania; son and daughter-in-law, Christopher and Kristin Letterman of Harpers Ferry, West Virginia, grandson, Trevor and granddaughter, Meghan. He is survived by his second wife, Virginia Pierson; daughter, Eryn Virginia Letterman of Chattanooga, Tennessee, grandson Aiden T. Jesser; and son, Benton Takota Letterman of Pittsburgh, Pennsylvania. Lastly, he is survived by his siblings, Wanda Mallory Welch, Amy Mallory Stevenson, Daniel Mallory, Dawn Mallory, Darryl Mallory, Tammy Mallory Shultz; and sister-in-law Trista Mallory. His brother Charles Mallory, Trista's spouse, passed away after a long illness on May 23, 2022.

Services for Skip will be held in Arlington National Cemetery at a date and time to be determined. May Skip's memory bring comfort to those who knew him. Those wishing to make donations in his memory may donate to American PTSD Association www.aptsda.com or your local animal shelter. Fond memories and expressions of sympathy may be shared at www.NelsenWilliamsburg.com.