Kentuckian tried to stake a claim on Cuba. It didn’t turn out well for him.
Mar 30, 2026
Kentuckian William Logan Crittenden might be happy to hear that Sen. Lindsey Graham, R-S.C., wants President Donald Trump to “free” Cuba after he finishes “freeing” Iran.
Going on 175 years ago, the 28-year-old nephew of U.S. Attorney General John J. Crittenden (who also served as a Bluegra
ss State governor, congressman and U.S. senator) died trying to wrest Cuba from Spain. “The U.S. has always had designs on Cuba,” said Murray State University historian Brian Clardy.
Crittenden helped lead the rag-tag Narcisco Lopez expedition that stormed the island in August, 1851. Spanish troops quickly forced the little band to surrender. They executed Lopez, 53, Crittenden and most of their men.
Organized in the U.S. before the Civil War, such freelance forays into Latin American countries were called “filibusters,” an Anglicized version of “filibustero,” Spanish for freebooter or pirate or plunderer.
William L. Crittenden
Filibustering “goes to the core of American exceptionalism,” Clardy said. “It’s the idea that it’s our divine right to be the hegemonic power in the Americas.” In 1845, journalist John L. O’Sullivan declared it was America’s “manifest destiny to overspread the continent allotted by Providence for the free development of our yearly multiplying millions.”
Clardy also said the exceptionalist idea that undergirded filibustering also is basic to President Trump’s foreign policy: a wanton disregard for U.S. and international law and the sovereignty of nations.“I think I can do anything I want with it,” Trump recently said of Cuba, while refusing to disavow using military force. “Whether I free it, take it, I think I can do anything I want with it.”
Mid-19th century Southern leaders were ever eager to expand slavery and they looked to the vast western land won from Mexico in the Mexican-American War of 1846-1848. But they also saw Cuba, where slavery was legal, as a potential source for more slave states. “Some even imagined the United States as a great slave-owning republic that would stretch across the Caribbean to Brazil,” according to “Milestones in the History of U.S. Foreign Relations, 1830-1860,” a former U.S. State Department website.
Lopez, a Venezuelan-born Cuban, was, “like some wealthy Cuban slave-owners … wary of shaky Spanish rule over the island,” the website says. He wanted the U.S. to annex Cuba to save slavery. “Cuban property owners were concerned that Spain would give in to British pressure to abolish slavery in Cuba,” according to the website.
Lopez organized several failed filibusters and lined up Crittenden for the last one. Born in Shelby County in 1823, he graduated from West Point in 1845 and fought in the Mexican-American War. Afterwards, he resigned his commission and settled in New Orleans, where Lopez organized his 400-man expedition. The filibuster consisted of Cuban emigres and U.S. volunteers, evidently including some more Kentuckians besides Crittenden.
Lopez’s force reached Cuba on Aug. 12, 1851. He hoped Cubans would rally to him; evidently few did, and his enterprise was doomed. (Clardy sees parallels between the Lopez fiasco and the botched 1961 Bay of Pigs invasion in which 1,400 CIA-backed Cuban exiles were routed in their attempt to topple Fidel Castro.)
Americans, especially Southerners, denounced the executions of Lopez, Crittenden and their men, though their filibuster was illegal under U.S. law. No one should have known that inconvenient fact better than the AG, the country’s top law enforcement officer.
Anyway, Crittenden’s martyred hero reputation back home was enhanced by the story of his death. Reputedly, he rejected a blindfold and refused the firing squad commander’s order to get on his knees and turn around so he could be shot in the back. “A Kentuckian always faces his enemy and kneels only to his God,” supposedly were his last words.
President Millard Filmore refused to condemn the executions and “public anger against Fillmore’s seemingly lukewarm support for expansion contributed to a Whig defeat in 1852,” the website says, adding that “growing antislavery sentiment in the northern United States and Spanish determination to hold on to Cuba eventually forced U.S. leaders to end attempts to acquire the island.”
Clardy said Trump is no more likely to free Cuba today than President William McKinley was in 1898 after Spain had to give up Cuba following its humiliating defeat in the Spanish-American War. American troops, which occupied the island following the conflict, were not withdrawn until Cuba agreed to allow the U.S. to establish Guantanamo Bay naval base and intervene in Cuban affairs when it wished. The U.S. sent troops in 1906-1909, 1912 and 1917-1922.
Cuba remained a U.S. puppet until Castro overthrew pro-American dictator Fulgencio Batista in 1959 and made Cuba a Soviet puppet.
Clardy expects Trump to install another rightwing, pro-American dictator who will reopen the island to exploitation by U.S. business interests. “Cuba hasn’t been free since Columbus arrived in 1492,” the historian said.
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