Winston Churchill is one of those historical figures who had a long list of accomplishments over decades yet is mostly known for just one specific time period, and Winston's time will forever be World War II.
But prior to the World Wars Churchill was already on the road to becoming a larger-than-life figure, having escaped from a Boer prison camp in South Africa in 1899:
After graduating from Sandhurst, Churchill took leave from the army and traveled to Cuba, where he reported on an uprising for a London newspaper. He subsequently served as a war correspondent and military officer, a dual role then permitted, in India, Sudan and South Africa. Upon arriving in South Africa in 1899, his armored train was ambushed by Boers, the descendants of Dutch settlers who were fighting the British at the time. Churchill was captured and marched to a prison camp, which he soon escaped from by scaling a wall at night, even as two of his fellow prisoners turned back. With no precise plan, Churchill luckily stumbled upon the house of a British coal mine manager, who hid him in a mineshaft for three days and then sent him on a wool-filled rail truck into Mozambique. From there, Churchill caught a ship back to South Africa and rushed to the front a newfound hero.
However, Winston's star almost fell instead of rising when he organized an amphibious assault during World War I that failed spectacularly:
Churchill’s political career began in 1900 when he was elected to Parliament, a position he would hold for more than 60 years. He secured his first cabinet post in 1908, and by 1911 had advanced to become First Lord of the Admiralty (the British equivalent of U.S. Secretary of the Navy). In this capacity, he prepared an amphibious assault during World War I against the crumbling Ottoman Empire. Churchill believed such action would allow the British to link up with their Russian allies, put added pressure on Germany’s eastern front and possibly even tip the balance of the entire conflict. But when Allied battleships entered the Dardanelles strait, located near present-day Istanbul, in March 1915, Ottoman fire sank three of them, severely damaged three others and sent the remainder into retreat. Allied troops similarly failed to gain ground during months of fighting on the adjacent Gallipoli Peninsula, suffering over 250,000 casualties in the process. Although Churchill lost his admiralty post as a result of the failure, he was eventually able to rehabilitate his reputation.