Born and raised in Pittsburgh, Pennsylvania, Chip Gregson spent two years of high school at Valley Forge Military Academy and then four years at the Naval Academy. He arrived in Vietnam in 1969, and was a platoon commander for nine months, 3rd Platoon, Alpha Company, 1st Reconnaissance Battalion. The Recon Battalion would Sneaky Pete around the jungle and “sometimes … we'd go out there and find some kind of fight to get mixed up in or start a fight. And then hope that the aviators … could come out and pull us out before anything got too exciting.” Gregson was wounded and spent 45 days in a hospital in Guam, and then returned to Vietnam as a company executive officer for a short time. He then became the assistant battalion operations officer. And then “because we had no more majors or captains left in the battalion below the level of the executive officer, I became the battalion operations officer.”