How did Winston Churchill die? Winston Churchill's Death: Sir Winston Leonard Spencer Churchill was a famous political leader from Great Britain during the 20th century. His early years as Prime Minister, during the London Blitz of World War II, proved especially challenging because he was alone in his desire to defy Adolf Hitler. Answer and Explanation: Winston Churchill died on January 24, 1965 at the age of 90. After he retired from his position as Prime Minister, Churchill suffered a stroke and became very ill. He died nine days later in his home in London.