On September 15, 1957, Simmons dropped out of school and joined the U.S. Navy, and was first stationed at Naval Station Bremerton in Washington, where he met Bersabe Rebecca "Becky" Ulibarri, whom he married in New Mexico on July 9, 1960. Over the next 18 years, the couple had seven children. In 1963, Simmons left the navy, and approximately two years later joined the U.S. Air Force. During his 20-year military career, Simmons was awarded a Bronze Star Medal, the Republic of Vietnam Gallantry Cross for his service as an airman, and the Airforce Ribbon for Excellent Marksmanship. Simmons retired from the air force and military service on November 30, 1979, with the rank of master sergeant.