The end of 1958 was marked by violent fighting that hastened the defeat of the Batista dictatorship and the triumph of the Revolution under Commander Fidel Castro. The capture of Yaguajay and the surrender of Santa Clara were significant victories for the rebels commanded by Camilo Cienfuegos and Ernesto "Che" Guevara.
On December 20, on Camilo's orders, the garrison of Mayajigua was attacked. An enemy squadron that had left the barracks for the airport was annihilated; the soldiers fled toward Yaguajay, and the town fell into the hands of the rebels. The successive defeats of the dictatorship's army in small towns propelled the rebel offensive toward Yaguajay, a key military objective on the invasion route of Column Two "Antonio Maceo" into the west, and one that would offer fierce resistance. Immediately after the capture of Mayajigua, the man later known as the Hero of Yaguajay began the siege of that city, located in the northern part of Las Villas province.
On the morning of December 21st, and continuing into the night of the following day, the firing on enemy positions commenced. The Hotel and the Yaguajay City Hall proved difficult to surround, as soldiers easily controlled all access points from their upper floors. They also positioned outposts on the streets leading to these locations, and a jeep constantly patrolled the surrounding area. The remaining soldiers, estimated at 280, were stationed at the barracks, one kilometer north of the city.
On the 23rd, Che Guevara visited the Yaguajay theater of operations and agreed with Camilo Cienfuegos that capturing the barracks would be difficult if the enemy insisted on defending it. In the early morning of the 24th, the Rebel Army intensified its fire and captured the hotel in a fierce battle that resulted in numerous casualties on both sides. On December 25, Che visited Yaguajay again and advised Camilo not to rush the assault on the barracks to avoid unnecessary casualties. He told him that he planned to secure the situation in Santa Clara so Camilo could act more calmly, as the plan was for Camilo to support Che in the battle that would unfold in that city with only about 300 men.
The fighting in Yaguajay continued until December 31, when the rebels received reinforcements of a mortar and a bazooka. With these, the barracks was subjected to a heavy attack and accepted unconditional surrender.
Simultaneously, after three days of fierce fighting, forces from Column Eight, Ciro Redondo, under the command of Ernesto "Che" Guevara, captured the city of Santa Clara on December 31, dealing a fatal blow to the dictatorship.
For the defense of Santa Clara, the Third Military District had over two thousand troops, a platoon of medium tanks, and another of light tankettes. It decided to defend the city using the Regiment's headquarters as its main base and reinforcing other strongholds within the city.
These strongholds included the Police Headquarters, the Provincial Government Palace, the Gran Hotel, the Martí Theater, the Jail, and the Courthouse. Squadron 31 would cover the Báez and Manicaragua roads; the so-called "Caballitos" barracks on the Central Highway; and the armored train in the Capiro hills, with control of the Camajuaní road and the Central Highway toward Havana.
To close off the province, Commander Ernesto "Che" Guevara ordered Commander Ramiro Valdés, with platoons led by Captains Armando Acosta Cordero, Olo Pantoja, and Eliseo Reyes (San Luis), to launch an offensive on the roads leading from Santa Clara toward Camagüey, attack the Jatibonico barracks, and advance into the interior, neutralizing the forces stationed there. Commander Víctor Bordón was ordered to occupy the territory west of Santa Clara, attack the bridge over the Sagua River and the Santo Domingo barracks, and prevent reinforcements from entering from the west.
Similarly, Commander Faure Chomón, with forces from the Revolutionary Directorate, would attack Trinidad and close the port of Casilda. Part of Commander Bordón's forces, under the command of Captain Julito Martínez, would cut the Cienfuegos-Santa Clara highway between Palmira and Cruces. The forces of the Second National Front of Escambray, whose leadership requested to participate in the offensive at the last minute, were to close the Cumanayagua-Cienfuegos highway, encircling the port city from the southeast.
Captain Rogelio Acevedo's platoon was to scout the city's approaches, obstruct the streets to hinder the passage of tanks, and attack the strongholds at the Courthouse and the Provincial Prison. Captain Roberto Rodríguez (El Vaquerito) would attack the Police Headquarters, and Captain Ramón Pardo Guerra's platoon would cut the railway line to derail and attack the armored train.
Captain Alfonso Zayas and his platoon would attack the enemy entrenched at El Capiro and subsequently the strongholds located at the Provincial Government building and the Gran H.