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Thompson entered the Army of the United States in 1941 and was assigned to the 504th Parachute Infantry Regiment, a part of the 82nd Airborne Division. In 1944, as a first lieutenant, Thompson led his men during an air raid as part of Operation Market Garden. The light in the jump bay of the platoon's C-47 Skytrain was later than expected, moving their landing zone from its intended location near Grave, Netherlands; the plane was passing over buildings when the paratroopers were signalled to leave the aircraft, and Thompson decided to wait until reaching several approaching fields.
Thompson led his platoon in an attack against the nearby bridge spanning the Maas River, which was defended by German forces supplemented by two 20 mm flak guns, one on the close side of the bridge and one across the river. The platoon opened fire on the German forces, killing four. Two trucks of German soldiers arrived on the scene, but they "showed no desire to fight ... [and] ran away". Thompson's platoon destroyed "electrical equipment and cables that they expected were hooked up to demolitions", and their bazooka operator destroyed the nearer flak gun, permitting the establishment of a roadblock on the bridge while waiting for the remainder of the 82nd Airborne. After the battle at the Maas bridge, Thompson also participated in the Battle of the Bulge, where he was given a field commission, and during the Allied occupation of Berlin, where he served as an aide to General James M. Gavin.
Thompson was wounded twice during the war, for which he received two Purple Hearts; fellow pitcher Robin Roberts later wrote that his Phillies teammates "understood that Jocko still carried around a considerable amount of shrapnel in his body". Other decorations included the Bronze Star with cluster, the Silver Star, and various awards from the Belgian, French, and Dutch governments.
In 2004, the bridge over the Maas River which Thompson's platoon secured 60 years earlier was renamed the John S. Thompson-Brug ("John S. Thompson Bridge"). Many veterans of World War II, as well as Thompson's wife, attended the ceremony.
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