The following two-part essay will analyze critically four of the ten greatest controversies of Sir Winston Churchill's career that are based on the 2015 BBC News Magazine article of T. Heyden. Churchill, often referred to erroneously as an "opportunist", navigated his political career as a thorough pragmatist. The four controversies of his career are: a) Being “anti-union” during the Tonypandy Riots in 1910, b) Permitting the usage of “Mustard gas” against the Kurds and Afghans in 1919, c) Deploying the Royal Irish Constabulary Special Reserve (“Black and Tans”) in January 1919, and d) Indifference toward the Bengal famine in 1943. These examples were selected randomly to reflect a balance of two foreign and two domestic incidents. In the second part of this essay, Churchill was often referred to as a “political amateur”when he withdrew troops at the Dardanelles Campaign of 1916. However, the following four documents support otherwise that Churchill's assessment that the campaign in the Dardanelles was "not a civilian plan foisted by a political amateur upon reluctant officers and experts". These documents are entitled, 1. Excerpts from Churchill's Resignation Speech- 15 November 1915. 2) Excerpts from a letter from Churchill to A. B. Law (Head of the Conservative Party)- 21 May 1915. 3) Cabinet Memorandum by Churchill defending his Policy of the Dardanelles Campaign- 5 August 1915, and 4) Communique sent to Rear-Admiral J. de Robeck (of the Dardanelles Campaign)- 1917.