World War II
Taylor's rise to the highest echelons of U.S. government began under the tutelage of General Matthew B. Ridgway in the US Army's 82nd Airborne Division when Ridgway commanded the division in the early part of World War II. In 1943, Taylor's diplomatic and language skills resulted in his secret mission to Rome to coordinate an 82nd air drop with Italian forces. General Dwight D. Eisenhower would later say that "the risks he ran were greater than I asked any other agent or emissary to take during the war." Hundreds of miles behind the front lines of battle, Taylor was forced by rules of engagement to wear his American military uniform, so that if captured he could not be shot as a spy. He met with the new Italian Prime Minister, Marshal Pietro Badoglio and General Carboni. The air drop near Rome to capture the city was called off at the last minute, when Taylor realized that it was too late. German forces were already moving in to cover the intended drop zones. Transport planes were already in the air when Taylor's message canceled the drop, preventing the suicide mission. These efforts behind enemy lines got Taylor noticed at the highest levels of the Allied command.
After the campaigns in the Mediterranean, Taylor was assigned to command the 101st Airborne Division, which was training in England, after the 101st's first commander Major General Bill Lee suffered a heart attack.
Taylor jumped into Normandy on June 6, 1944, with his men. He was the first Allied general to land in France on D-Day. He commanded the 101st Airborne Division for the rest of the war, among other things during Operation Market Garden in The Netherlands, but missed out leading the division during its most famous conflict, the Battle of Bastogne during the Battle of the Bulge, because he was attending a staff conference in the United States. The Division Artillery commander, Brig. Gen. Anthony McAuliffe exercised command in his absence. Some of the paratroopers resented Taylor for this later. General Taylor called the defense of Bastogne the 101st Airborne Division's "finest hour" of the war and stated that his absence there was one of his greatest disappointments in World War II.
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