[5] In 1941, Fry volunteered for and was assigned duty as a U.S. Military Observer with the British 8th Army then engaged in combat operations against German and Italian forces in the western Libyan Desert.

[6][9] Following his retirement from the United States Army in 1957, Fry became an advocate for military readiness and was a founder, lifetime member, board chairman, and president of the National Association of the Uniformed Services.

He was a leading figure in the evolution of Civil War reenactments into their modern form and was the driving force behind the Centennial re-enactment of the First Battle of Bull Run, July 21, 1961.

[10] Fry also wrote the book Combat Soldier, which is a documentary of the U.S. Army World War II Italian Campaign and a tribute to the American "doughboys" who fought there.

[1] The official United States Army citation for Fry's World War II Distinguished Service Cross reads: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting the Distinguished Service Cross to Colonel (Infantry) James Clyde Fry (ASN: 0-15023), United States Army, for extraordinary heroism in connection with military operations against an armed enemy while serving as Commanding Officer of the 350th Infantry Regiment, 88th Infantry Division, in action against enemy forces on 4 October 1944, in Italy.

Colonel Fry led his regiment, which was extremely tired from its arduous mountain fighting of the preceding days, in a swift and well executed maneuver towards Mount Battaglia and succeeded in taking this feature before the enemy had fully organized its defenses.

Although his regiment was completely exposed on both flanks, and subjected to terrific artillery and mortar fire as well as flame throwers, Colonel Fry planned and supervised his defense in such a manner that the hill was held.

On one occasion while he was with his front line elements, Colonel Fry was wounded in the arm by a shell burst, but remained with his troops until ordered by higher authority to go to the rear for treatment.

Colonel Fry's courage and brilliant leadership contributed immeasurably to the success of a vital operation in the Allied advance towards the Po Valley and provided a lasting inspiration to those who served under him.