Bolton enlisted in the U.S. Navy in November 1939 and trained as a seaman at Pensacola Naval Air Station in Florida. He was selected for the naval enlisted aviator program and earned his wings as a naval aviator in April 1942. In May 1942, he was assigned to Patrol Squadron 42, flying PBY Catalina amphibious patrol planes, at Fort Glenn, Alaska, in the Aleutians. Bolton spent his entire flying career in the Aleutians, including some time ferrying Catalinas from the west coast to Alaska.

He earned an Air Medal from the U.S. Navy during the Aleutian Islands Campaign in June 1942. Imperial Japanese forces had attacked Dutch Harbor on Unalaska Island and seized Attu and Kiska Islands in Alaska. His citation, signed by the Secretary of the Navy, reads:

For meritorious achievement while participating in aerial flight as an aviation pilot in action against enemy Japanese forces during the Aleutian Islands Campaign, June 1 to June 15, 1942. Under the most severe weather conditions of high winds, snow, rain and fog, and in the face of persistent attack, Bolton, with conscientious devotion to duty, made repeated flights on tactical missions and displayed zeal and determination in combat against the enemy. His fine courage throughout was in keeping with the highest traditions of the United States Naval Service.

During spring and summer 1943, the U.S. military retook Attu and Kiska Islands. U.S. forces patrolled these waters and made occasional bombing missions against the Japanese in the Kurile Islands off the coast of the Soviet Union.

Bolton’s logbook recorded his participation on one of these bombing missions on December 30-31, 1943, to the northern island of the Kuriles, Paramushir. The flight lasted almost 12 hours. Paramushir is located just off the southern tip of the Kamchatka Peninsula of the former Soviet Union. There were numerous Imperial Japanese Army and Navy positions over the entire island of Paramushir. Pilots flew straight over the target over a mile high in the air at about 100 miles per hour. They dropped flares so they could see the target area and then dropped 1,000 pounds of bombs on the target.

The War Diary from Bolton’s squadron listed the weather conditions on Monday, January 17, 1944, as low clouds with very windy blowing snow, sometimes making it impossible to see anything at all. Bolton’s plane, tail number 33969, “crashed and burned” in Massacre Bay in Attu immediately after takeoff. They suspected a failure of the port (left) engine. None of the crew survived. All flights were cancelled the next day due to weather; the War Diary recorded the same observations as the day before.

A death gratuity of six months pay, $1,417.50, was sent to his father in February 1944. His beneficiary slip indicated he was not married. His personal effects, including his logbook, gold aviator wings, and a Bulova watch, were forwarded to his father in June 1944.

Family stories told of James’ fiancée, a woman named Lucy. She went on to marry one of his best friends after the war and had a son. Both Lucy’s husband and son were killed in a plane crash. She later contacted Bolton’s stepmother and wrote that “every man I have ever loved was killed by a plane.”