Churchill in Cuba: The Best War Education Bullets Can Buy

The Spanish Army’s 1700-strong find and fight column had been marching over a week through the jungles of central Cuba looking for rebels. Then, suddenly, in the humid, hot opening days of December, 1895, they found themselves under sustained sporadic fire from enemy insurgents for forty-eight straight hours. British Army subaltern (lieutenant) Winston Churchill had just turned twenty-one-years old and was embedded as an observer with Spanish forces. He described that incoming rebel fire sounded “like the buzz of an offended hornet.” The combat was so constant, Churchill wrote, “no soldier ever goes a yard without his weapon.”

The skirmishing culminated with a meeting engagement between the Spanish and a rear guard of Cuban insurgents. Churchill judged it a “draw,” but one that essentially went to the rebels:

Here you have a General of Division and two thousand of the best troops in the island out for over ten days in search of the enemy, overcoming all sorts of difficulties, undergoing all kinds of hardships, and then being quite contented with killing thirty or forty rebels and taking a low grass hill which was destitute of the slightest importance.

“Such tactics make the war interminable” for the Spanish, Churchill wrote of the Battle of La Reforma. Right or wrong, what’s noteworthy about Churchill in Cuba is the practical experience he gained in assessing war, across several dimensions, for himself. Anybody can read about a war; to assess a conflict for oneself is a uniquely important skill which is at the very heart of the military profession. And those military officers that wish to develop their own analytical expertise would do well to march in Churchill’s bootsteps.

The British Army, in those days, divided the year into training and leave blocks that provided officers large chunks of time off to pursue personal interests. Churchill’s first annual winter leave after receiving his commission as a cavalry officer in February 1895, he exploited family connections to arrange for the blessing of the British and Spanish governments’ to report on how effective the 200,000 Spanish soldiers deployed in Cuba were at pacifying the island’s rebellion. Churchill arrived in Havana on November 18, 1895.

We know Churchill learned a great deal because he penned a series of five dispatches on the Cuban War of Independence for the Daily Graphic, a British newspaper (they appeared in print on December 13, 17, 24, 27, 1895, and January 13, 1896, titled “The Insurrection in Cuba,” and signed “W.S.C.”).

More than 120 years later they still read well, and address the key issues in the conflict, including Cuba’s raw value, insurgent objectives, what caused the conflict, the war’s consequences, each belligerent’s advantages, tactics, and, most importantly—Churchill’s overall strategic assessment.

  • Value: He noted that nearly nobody in England recognized Cuba’s “wealth,” principally derived from its continuous production of the world’s best sugar.
  • Objectives: Churchill perceived the rebels were out to demonstrate “the power they have” to “obtain recognition” as a belligerent from the United States and “procure the intervention” of a European state.
  • Cause: He found the war was caused by a “corrupt” Spanish colonial government that terribly “overtaxed” the Cubans.
  • Consequences: The first thing Churchill saw in Cuba was the corpse of a Spanish lieutenant who had been shot for “neglect of duty.” He also took note of the civilian population’s “suffering and misery,” and that smallpox and yellow fever had run rampant.
  • Advantages: Churchill saw the insurgents as amateurs that held the distinct advantage of “constant and accurate intelligence,” who could disappear because their only uniform was “a badge.” Weapons-wise, the Cuban rebels were “very formidable” with the machete, which he called the country’s “national weapon.” The rebels suffered two main deficiencies: they had almost no ammunition, and even if they did, they were “very bad shots.” The Spanish infantry, oppositely, impressed Churchill as professionals, who noted they “march splendidly” and covered 26 miles in a single day despite bad roads and carrying full kit.
  • Tactics: Churchill counted rebel tactics as: “burning cane fields, shooting from behind hedges, firing into sleeping camps, destroying property, wrecking trains, and throwing dynamite.” Most interestingly, he noted the rebel proclivity for attaching crude phosphorous grenades to Cuban grass snakes’ tails for the purpose of setting loose amongst Spanish troops to disguise the explosive’s “authorship.” (Today, this might be a “SB-IED,” or “snake-borne, improvised explosive device.”)
  • StrategicAssessment: “As long as the insurgents choose to adhere to the tactics they have adopted,” Churchill believed, “they can never be caught nor defeated.” For this reason, he thought it “probable” that “compromise alone is possible” in the conflict. He also advised readers not to be fooled by the battles there, which he found to be “devoid of importance.” Instead, Churchill suggested the better war metric was the “position of the insurgents” (i.e., look for the relative strategic value of the key terrain and towns the rebels held).

Besides cigars and his first military decoration (bestowed by the Spanish Army), what did Churchill take from his eighteen days in Cuba?

Succinctly put: He assessed war for himself, from close enough to smell the gunsmoke.

And then he practiced his powers of conflict assessment some more. Over the next four years, he participated in three more wars (Afghanistan, Sudan, and South Africa), wrote five books and published 215 magazine and newspaper articles, mostly on conflict. One contemporary account had it that by the age of twenty-five, Churchill had “seen as many campaigns as any living general.”

What might today’s military officers take from Churchill’s early experience with war?

While reasonable minds can find fault with some of Churchill’s strategic decisions in his life’s full sweep, on the biggest, most important issues in the all-important Second World War, his strategic acumen stood far above nearly all others.

Churchill’s sharp strategic sense seems to have been forged in fiery furnaces like Cuba, his instincts honed by practice so he was well-equipped to estimate strategic probabilities and spot the factors that truly matter at war.

Basil H. Liddell Hart has described “two forms of practical experience” when it comes to war, “direct and indirect.” “Indirect” war experience includes the reading of history, simulation,wargames, staff rides, and even the consumption of film and fiction. Those are undoubtedly important for width in learning.

But we can also see the value of direct experience with war in Churchill’s adventure in Cuba. To immerse oneself in a war—to study the strategy, society, and self while at war—this is a deeper, perhaps stronger, form of war study.

The modern American military would do well to follow Churchill’s lead. Military officers shouldn’t need Churchill’s family connections to avail themselves of this sort of experiential learning. The U.S. military ought to routinely send more observers to learn firsthand about foreign wars. It’s already happening, albeit in very limited quantities, through the Modern War Institute’s contemporary battlefield assessments and the U.S. Army’s Asymmetric Warfare Group. Such programs should be expanded.

Because it may well be the best way to prepare for war is, simply put, to go to war like Churchill did. Even if dangerous, the best education for war might be the one that only bullets can buy.