After ambushing an armored train sent to reinforce government troops, Ernesto 'Che' Guevara's guerrilla column overran Santa Clara, Cuba's third-largest city, in a decisive battle that broke the Cuban Army's will to fight. News of the defeat reached Havana that night; by early morning on December 31 Batista and his inner circle boarded planes into exile, effectively ending his seven-year dictatorship and clearing the way for Fidel Castro's forces to enter Havana days later.
By late December 1958, Fidel Castro's 26th of July Movement had spent two years waging guerrilla war from the Sierra Maestra mountains, gradually winning peasant support and eroding the morale of Batista's demoralized, poorly led conscript army. Castro dispatched two columns toward central Cuba to cut the island in half: one led by Che Guevara, the other by Camilo Cienfuegos.
Guevara's column, numbering only a few hundred fighters against thousands of government troops, targeted Santa Clara, a provincial capital astride the vital central highway and railway. His men derailed and ambushed an armored train packed with troops and munitions sent as reinforcements, using a captured bulldozer to rip up the tracks—a coup that yielded weapons for hundreds more rebels. house-to-house fighting through December 29 and 30 broke the garrison's resistance.
Word of Santa Clara's fall convinced Batista the war was lost. In the early hours of January 1, 1959, he fled Havana by plane for the Dominican Republic with an entourage and a fortune in cash, having decided there was nothing left to defend. Castro's forces entered Havana within a week, and Guevara—an Argentine doctor turned guerrilla commander—emerged as one of the revolution's most mythologized figures.
Key people: Che Guevara, Fulgencio Batista, Fidel Castro