Sam Bailey was born on October 8, 1920, in Massachusetts. He enlisted in the U.S. Navy on January 23, 1942, and completed basic training at NTC Newport, Rhode Island, in February 1942. After spending 2 months at Reception Station New York, Petty Officer Bailey served as a Gunner's Mate aboard the destroyer USS Ellis (DDD-154) during its operations escorting convoys in the Atlantic Ocean from April 1942 to October 1944. He spent 2 months at the Reception Station in Washington, D.C., and then served aboard the destroyer escort USS Hanna (DE-449) from her commissioning on January 27, 1945, to April 1945. Petty Officer Bailey was then accepted for Underwater Demolition Team training, and he completed training at Fort Pierce, Florida, in June 1945. His next assignment was with Underwater Demolition Team THIRTY (UDT-30, later redesignated UDT Team FOX, and then UDT-2) at Oceanside and then Coronado, California, from June 1945 to 1946, followed by service with UDT-2 at Naval Amphibious Base Little Creek, Virginia, from 1946 until UDT-2 was renamed UDT-21 in June 1954. Chief Petty Officer Bailey then continued service with UDT-21 at NAB Little Creek from June 1954 until his retirement from the Navy on May 1, 1975. Sam Bailey died on November 18, 1998, and was buried at Chesapeake Memorial Gardens in Chesapeake, Virginia.

His Navy Commendation Medal Citation reads:

For outstanding meritorious service in the performance of his duties while serving on continuous sea duty with Underwater Demolition Teams Fox, Thirty, Two, and Twenty-One over the past thirty years and in the service of the United States Navy over the past thirty-three years. Chief Petty Officer Bailey, more than any other person, contributed to the molding, shaping and development of the men of the Atlantic Fleet Underwater Demolition Teams and the inimitable reputation associated with Navy Frogmen. As a platoon member during his distinguished career with UDT, Chief Petty Officer Bailey consistently performed his demanding and hazardous duties of diving, demolitions, and parachuting in an exemplary and highly professional manner. In addition, Chief Petty Officer Bailey participated in and materially contributed to the overall operational performance and readiness of UDT Platoons on numerous Caribbean and Mediterranean deployments. His diligent efforts and devotion to duty inspired all who observed him and contributed significantly to the fulfillment of his unit's mission. He has become a legend in the Naval Special Warfare Community. Chief Patty Officer Bailey's exceptional professional ability, unparalleled continuous service to the Navy's Underwater Demolition Teams and loyal dedication to duty throughout his entire career reflected great credit upon himself and the United States Naval Service.