Esther Allen has an excellent piece in NYR Daily about the history of US-Cuba relations, including this fascinating story about the Cuban flag:
For its part, the US government had had an eye on Cuba at least since the beginning of the nineteenth century, when Thomas Jefferson tried without success to buy the colony from Spain. Half a century later, a Venezuelan adventurer named Narciso López recruited a band of filibusters in the United States to invade the island. Supported by Mississippi Senator [and future Confederate president] Jefferson Davis and others, López hoped to annex Cuba to the US as a slave state, thereby bolstering the Southern states’ clout in the Senate and averting the threat of civil war. The flag López created—red, white, and blue, with stripes and a star—flew for the first time in lower Manhattan in the year 1850, raised by The New York Sun over its headquarters at the corner of Nassau and Fulton Streets in a show of support for annexation.
López’s scheme failed, but commitment to slavery would remain an element of US-Cuba relations for some years thereafter. [ … ] The first act of the Cuban independence movement after it declared war on Spain in 1868 was to free the slaves under its jurisdiction, but the Spanish Empire devoted enormous resources to maintaining its last footholds in this hemisphere. The Cuban insurgents lost their first war of independence in 1878, and slavery remained legal on the island until 1886.
By that point, the flag the filibusters had brandished—“López’s flag” as the Cuban insurgency’s greatest leader, José Martí, called it—had become the banner of independence. The lives lost in its service transformed it from a petition for annexation into the flag of Cuban sovereignty. The great Cuban ethnomusicologist Fernando Ortiz coined a term for this complex cultural process, which he identified as a fundamental dynamic of Cuban history. He called it transculturación and believed that it grew out of the resilience of the Africans, brought to Cuba against their will, who coopted the alien cultural symbols available to them to create new and vibrant meanings from the unspeakable trauma they had endured.
Jumping ahead to the present day — which recently saw the US flag hoisted at the US Embassy in Havana for the first time since 1961 — Allen concludes with some observations about Cubans’ attraction to our flag:
Walk down any street in Cuba and you’ll also encounter riffs on the American flag. Reporters from the US have been surprised to note that Cubans like to sport shirts or leggings emblazoned with the flag of a nation that has embargoed their country for more than half a century. And why shouldn’t they? After all, the Cuban flag evolved from the same shapes and colors. None of us can say what any person means by the design on the t-shirt he happens to be wearing; it may be an expression of support for the Cuban government’s policy of normalization, an expression of antipathy for the Cuban government, or the proud showing off of a gift from an uncle in Rochester, New York, or a sister in Union City, New Jersey.
For more from a nice photo essay on the US flag as a fashion statement in Cuba, check out Los cubanos ya se lucen la bandera de EEUU (“Cubans are already wearing the US flag”), from the Peruvian site La Mula.