In 1957, he became qualified in the U-2 and would join the 4080th Strategic Reconnaissance Wing and, "became top U-2 pilot with over one thousand hours, making him a vital part of the United States' reconnaissance operation over Cuba in late October of 1962."
After the flight of Richard Heyser on October 14, Which confirmed the presence of Soviet missiles in Cuba, further flights were ordered. On October 27, 1962, Anderson took off in a U-2 from McCoy Air Force Base in Orlando, Florida headed for Cuba. A few hours later, an SA-2 surface to air missile supplied by the Soviets was fired. It detonated within a close proximity to Anderson's U-2 and shrapnel is thought to have punctured his flight suit, depressurizing it, causing him to likely experience hypoxia. Either that, or the resulting crash took his life.
Rudolph Anderson was the only casualty resulting from direct combat during the Cuban Missile Crisis. For his actions, he was awarded the very first Air Force Cross, the Air Force Distinguished Service Medal, the Purple Heart and the Cheney Award.
His Air Force Cross citation reads:
The President of the United States of America, authorized by Title 10, Section 8742, United States Code, takes pride in presenting the Air Force Cross (Posthumously) to Major Rudolf Anderson, Jr., United States Air Force, for extraordinary heroism in connection with military operations against an armed enemy while serving as Pilot of a U-2 airplane with the 4080th Strategic Reconnaissance Wing, Strategic Air Command (SAC), from 15 October 1962 to 27 October 1962. During this period of great national crisis, Major Anderson, flying an unescorted, unarmed aircraft, lost his life while participating in one of several aerial reconnaissance missions over Cuba. While executing these aerial missions, Major Anderson made photographs which provided the United States government with conclusive evidence of the introduction of long-range offensive missiles into Cuba and which materially assisted our leaders in charting the nation's military and diplomatic course. Through his extraordinary heroism, superb airmanship, and aggressiveness in the face of the enemy, Major Anderson reflected the highest credit upon himself and the United States Air Force.
Anderson played a willing, honorable role in the history of this great nation. He served, not only at this time, but also during the Korean War, with distinction and pride. His commitment to excellence in the service of the country he loved should be remembered and highly regarded by those who follow.
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