His first two schools weren't successful, but his father then enrolled Winston in the Harrow School, a boarding school in London, where he began his military career on the Harrow Rifle Corps (Bio). He struggled at first, failing the admission test twice before finally passing it. Once he got in he finished 20th in his class once he graduated. Winston never really had a close relationship with either of his parents. His mother very rarely came to see him at Harrow, and it's said that Winston "knew his father more on reputation than any close relationship they shared" (Bio). Winston's father died when Winston was only 21 years of age. .
After Winston finished school, he began his military career for Britain by joining the Fourth Hussars in 1895. While it was a short stay, he fought in the battle of Omdurman in 1898, and wrote two books about the experiences he'd had while there, one called The Story of the Malakand Field Force in 1898 and The River War in 1899. He then left the army in 1899 and began working as a correspondent for the Morning Post. While in South Africa reporting on the Boer War, Churchill was captured and taken hostage by Boers. He managed to escape by trekking over 300 miles to Mozambique, and after he escaped and returned to England he wrote a book called London to Ladysmith (Bio). In 1908, Churchill met a strong-minded woman of Scottish decent named Clementine Hozier. He and Clementine wrote each other back and forth for a few months, and Churchill invited her to every event he could just so he could see her. He and Clementine were very fond of each other. He and Clementine went for a stroll through the park on a cloudy Tuesday afternoon. It seemed like just a normal walk until the rain started pouring down on them, hard enough to make them get under shelter of "a little Greek temple overlooking the palace's great lake" (Manchester, Visions of Glory,397).