As Bradlee writes in his memoir, "A Good Life": "On August 8, 1942, I graduated from Harvard by the skin of my teeth at 10 a.m. At noon, I was commissioned an ensign in the U.S. Naval Reserve with orders to join a new destroyer being built in Kearny, New Jersey. And at 4 p.m., I married Jean Saltonstall, the first and only girl I had been with. I was not yet twenty-one. I had never been west of the Berkshires or south of Washington, D.C., and I was on my way to some place called the South Pacific, which was not yet a musical. The education of Benjamin C. Bradlee was finally under way."

Bradlee's marriage to Jean, daughter of former Massachusetts governor and then-U.S. Sen. Leverett Saltonstall, would last just over 10 years.

His work in the Navy included a two-year stint onboard a Navy destroyer before he was transferred to naval intelligence where he reportedly handled classified communications.