George Caldwell was born on August 19, 1901, in Columbus, Ohio. He enlisted in the U.S. Navy on April 15, 1920, and served as an electrician's mate until leaving active duty on May 5, 1922. EM3c Caldwell re-enlisted in the Navy on May 13, 1924, and served aboard the patrol vessel USS Niagara (PY-9) from June 1924 until leaving active duty on March 28, 1928. He then re-enlisted in the Navy for a third time on May 11, 1928, and attended the Submarine School at Submarine Base New London, Connecticut, from June to September 1928. His next assignment was aboard the submarine USS S-16 (SS-121) from November 1928 to May 1931, followed by service at Fleet Air Base Pearl Harbor, Hawaii, from July 1931 to August 1933. EM1c Caldwell served as an instructor with the Submarine School at New London from November 1933 to November 1935, and then served aboard the submarine USS Tarpon (SS-175) during her fitting out from December 1935, through her commissioning in March 1936, and operationally until October 1940. CEM Caldwell served at Canacao in the Philippines from October 1940 to January 1941, then aboard the submarine tender USS Canopus (AS-9) from January to February 1941. His next assignment was to Groton, Connecticut, for the fitting out of the submarine USS Grunion (SS-216) from June 1941, remaining aboard after her commissioning in April 1942, and was then appointed a Warrant Officer. He was killed in action aboard the Grunion on July 30, 1942, during a confrontation with the armed Japanese freighter Kano Maru. The ship was found by a search team on August 22, 2007, and the U.S. Navy announced the sunken vessel located off the coast of the Aleutian Islands is the World War II submarine USS Grunion (SS-216) on October 1, 2008.

His Navy Commendation Medal Citation reads:

For meritorious conduct as a member of the crew of the U.S.S. GRUNION which destroyed three enemy destroyers while engaged in a war patrol in enemy controlled waters. Despite severe and persistent anti-submarine measures resulting from these three successful attacks, the GRUNION was brought safely through the counter attacks and continued an aggressive war patrol. As a member of the crew of the GRUNION, your performance of duty was an important and material contribution to the prosecution of this war.