Winston Churchill was born November 30, 1874 in Oxfordshire, England. His father, Randolph Churchill was chancellor, and his mother Jennie Churchill was a beautiful woman. Winston lived in Benninghan Palace. Winston was a chunky boy with a mop of red hair. When he was young he spoke with a stutter. All of Winston's high hopes annoyed everyone. When Winston was six his brother John was born. Winston said that his mother was like a star. He admired her, but at a distance. Winston liked to play with his toy soldiers. Winston stood in wonder and fear of his father, Randolph. At age twelve Winston was sent to Harrow middle school, a leading secondary school. His position was last class, last chair and in that position he stayed. After Harrow Winston was sent to a military school at Sand Hurst. He failed the entry test for Sand Hurst two times before he passed. He graduated eighth in a class of 150.

His first military job was in the fourth Hussars as a second lieutenant. That is a Calvary unit. Winston went to war in Cuba. His family told him to go as an observer. He did. He wrote five colorful articles for the English newspaper. Winston came back from Cuba with the love of Havana cigars. In 1896 his regiment went to India. There he learned to like polo and read some books. The books by Thomas B. Macaulay and Edward Gibbon interested him the most. In 1897 Winston learned that fighting had broken out. He got two newspapers to hire him.