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Winston Churchill, military observer in Cuba
Winston Churchill as a Subaltern in the 4th Hussars, February, 1895
Cuba 1895
One of the most curious events in the Spanish-Cuban-American war was the presence of Winston Churchill (1895) much before the US entry into the war. Churchill was gathering information as a military observer. There are even some who infer that the information on tactics and methods used by the Spanish was put to work in subsequent Boer War, and led to the eventual victory of the British forces in that South African War.
It is interesting to speculate that a much more complete military style copy of Churchill`s reports may exist somewhere in the vast archives of the British Empire, or in the private papers of his son Randolph. In support of this, one can infer tantalizing hints by Randolph, when he refers to his father Winston Churchill`s advice to him at the time of the Spanish Civil War so as not to appear to be a spy. In addition, it is noted below Winston Churchill at the time of his visit to Cuba was on a leave of absence from his regiment.

However, one should bear in mind what a knowledgeable source points out (for further details see Davis 1906): `Churchill`s visit to the front was typical of ambitious British (and German, Japanese, Russian, Turkish, and even American) military officers of the day. They got experience in seeing combat, and the resulting reports filed at home could help boost one`s chances of promotion. In many cases it was also lucrative in that the observers would also write articles for popular magazines. The American and Spanish armies were loaded with observers. At times, however, the observers were not necessarily welcomed by their own units, who had to stand the boring times (with the lack of promotion) at home, while the officers of means could get a leave of absence and go gallivanting.`
What we see below are accounts by a brilliant, but still very young, man who just turning twenty-one as yet does not fully understand the complexities of irregular war, nor the subtleties of Cuban politics and racial relations. For instance Churchill accepts the Spanish propaganda point that Antonio Maceo was a Black separatist, a while it is now clear that Maceo, not only was not completely black (he was mulatto), but was an avowed integrationist. The Spanish view of the war was of course quite different from the Cuban perspective. Whatever, South Africa, the Sudan, Gallapoli etc, will teach Churchill other lessons, and a great man will be forged.

by by Randolph Churchill and Larry Daley
Article ID 193
First Article 193 of 815 Last
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