Cuba faces its most precarious moment since the 1959 revolution as the Trump administration's oil blockade triggers a humanitarian emergency. The Communist government, which has outlasted 13 U.S. presidents, now confronts economic collapse with roughly 2.75 million Cubans fleeing since 2020, most heading to the United States.

Images from The New York Times archives document seven decades of political turmoil, from Fidel Castro's guerrilla campaign in the Sierra Maestra mountains to the 1961 Bay of Pigs invasion's failure. The Cuban Missile Crisis brought the world to the brink of nuclear war when Moscow secretly deployed missiles to the island, triggering a 13-day standoff with Washington.

The revolution's early triumphs in literacy and healthcare gave way to decades of Soviet alignment, U.S. trade embargoes, and economic stagnation. Old Havana's crumbling facades and vintage American cars reflect a country frozen in midcentury time. Castro's death in 2016 closed one chapter but failed to alter Cuba's economic trajectory, leaving the government now negotiating with Washington to resolve their latest confrontation.