Returning from the Boer War aboard the S.S. Dunottar Castle, July 1900. Winston Churchill is seated in the second row, second from the right.
Returning from the Boer War aboard the S.S. Dunottar Castle, July 1900. Winston Churchill is seated in the second row, second from the right.
Wikipedia/Burnham Family Collection - Source
License: Public Domain

Churchill Acts As War Correspondent During the Second Boer War

In 1899, Winston Churchill headed to South Africa as a newspaper correspondent for the Morning Post to cover the Boer War between British and Dutch settlers. Unfortunately, he was present at an ambush of an armored train and captured by enemy Boer soldiers. On November 18, 1899, Churchill along with the other prisoners arrived in Pretoria at the prison called the State Model Schools. On the night of December 12th, when the prison guards turned their backs on Churchill, he took the opportunity to climb over the prison wall. Wearing a brown flannel suit with £75 (the equivalent of $375) and four slabs of chocolate in his pocket, Churchill walked on leisurely through the night in hopes of finding the Delagoa Bay Railway. So began his great escape and journey to freedom.

What men they were, these Boers! I thought of them as I had seen them in the morning riding forward through the rain--thousands of independent riflemen, thinking for themselves, possessed of beautiful weapons, led with skill, living as they rode without commissariat or transport or ammunition column, moving like the wind, and supported by iron constitutions and a stern, hard Old Testament God.

— Winston Churchill