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If you were to ask any 21st-century American about Cuba, most of the stories that would come to mind would be those of the Missile Crisis, the world on the brink of nuclear collapse, and the repression of freedoms against the island’s inhabitants by a socialist tyranny. And they are right.

But the rich connections between the island and the United States are not limited to the last 70 tumultuous years. There is a whole current of prior ties, in which solidarity and alliance between regional neighbors prevailed.

We discussed these with Cuban-American historian Octavio de la Suarée, who for years was a professor and head of the Department of Language, Literature, and Culture at William Paterson University in New Jersey, and who presides over the Cuban Academy of History in Exile. Here is part of that long conversation on the 250th anniversary of the United States.

The American Henry Reeve was a scourge to Spanish troops during the Ten Years’ War in Cuba. Is that so?

Reeve’s units frequently outnumbered Spanish forces and often defeated larger enemy contingents through daring tactics and relentless determination. His combat experience as a veteran American gave him an advantage in battle, and his fearlessness earned him a well-deserved reputation among the Cuban revolutionaries. In one notable engagement, Reeve fearlessly leaped onto an enemy artillery battery to help secure victory, a feat that would guarantee his promotion to Brigadier General in 1873. Throughout the war, Reeve suffered more than 10 wounds. He was held in high esteem alongside legendary Cuban military leaders such as Generals Máximo Gómez and Antonio Maceo.

Henry Reeve always led the charge, first in line, thus demonstrating exceptional courage in battle. The brigadier general participated in several battles during this period, including the engagements of Las Yeguas, La Luz, and Atadeo. On September 28, 1873, during the Battle of Santa Cruz del Sur, in one of his most remarkable feats, he personally led the assault on a Spanish artillery battery, capturing it in hand-to-hand combat.

Was it during this battle that he suffered a brutal wound?

Exactly. It was devastating. Shrapnel from Spanish artillery fire severely damaged his right leg near the hip, and he was subsequently transported to a military hospital in Najasa. The wound, his eleventh in combat, left him unable to ride a horse without assistance. After a six-month recovery period, he rejoined the fight against the enemy, his wound fitted with a metal prosthesis and specialized riding equipment to secure him to his horse, allowing him to continue leading his troops in machete charges against the Spanish forces.

On June 20, 1874, Reeve was given command of the First Division and was wounded again during the Battle of San Antonio de Camujiri on July 4, 1874.

In January 1875, Reeve provided artillery cover for Cuban forces crossing the Spanish defensive line known as the Júcaro-Morón Trocha, allowing Máximo Gómez’s invading contingent to advance westward.

Later that year, Reeve requested to participate in the western invasion and was assigned to Las Villas on November 5, 1875. Recognizing his leadership skills, the Cuban general Máximo Gómez entrusted him with the command of the Second Division, responsible for the Camagüey and Villareño cavalry units, charging him with extending the war to the western regions of the island. On November 30, 1875, Reeve led a cavalry squadron across the Hanabana River, becoming the vanguard of the invading force. He also played a key role in the first invasion of western Cuba, marking his participation in the Battle of Las Guásimas.

By May 1875, he had reached the plains of Colón, and by 1876 he had entered Havana province. Over a period of six months, he led a campaign that resulted in the destruction of more than 50 sugar mills, attempting to cripple the Spanish economy that sustained the war effort. Between 1875 and 1876, he fought in the battles of Los Abreus, Crocodilos, Quemado Grande, Santa Teresa, Espinal, Lagunillas, and Orbea. In July 1876, he was wounded again in the Battle of the Hanabana River, one of his last major armed engagements before his final battle near Yaguaramas. Despite these successes, internal divisions among the Cuban revolutionaries, including caudillismo, regionalism, and factionalism, weakened the independence movement. As a result, Reeve found himself leading a significantly reduced force.

On August 4, 1876, Reeve fell in combat. How did this happen?

On the savanna near Yaguaramas, Reeve and his men were ambushed by Spanish troops and guerrilla forces near Alba de Tormes. During the battle, Reeve’s horse was killed, leaving him stranded on the battlefield.

His personal aide, Rosendo García, tried to get him another mount, but Reeve ordered him to seek cover to avoid being killed. Reeve decided to stand his ground and remained beside his dead horse, armed with a machete in one hand and a revolver in the other.

The brigadier general then suffered multiple gunshot wounds, including one to the groin and another to the shoulder. As the Spanish troops approached, he was hit by three more shots. Recognizing that he was about to be captured and out of ammunition, he took his own life with a shot to his right temple.

His remains were sent to the city of Cienfuegos as a war trophy and publicly displayed in the Reina Cemetery, although the exact location of his burial remains unknown. At the time of his death, he was wearing a white jacket with a vest, new boots, trousers, a belt, and a fine pocket watch. His body bore numerous wounds. Although Reeve was not Cuban by birth, he is remembered today as a Cuban National Hero, a soldier who fought selflessly for his adopted homeland.

After the failure of the Ten Years’ War, the Spanish-American War broke out in 1898. This war ended the Spanish Empire and marked a period in which Cubans and Americans took up arms together on the battlefields. How did Cuba reach that point?

The failed expedition of the Venezuelan Narciso López to Cuba in August 1851, with the purpose of liberating the island from the vestiges of Spanish colonialism in the Americas, would pave the way for the three subsequent sustained armed conflicts that would culminate in the establishment of the Republic of Cuba in 1902: these are the Ten Years’ War (1868-1878), the Little War (1879-1880), and the War of Independence (1895-1898).

As we saw earlier in the answer to the first question, the Americans participated from the very beginning, and there we see the actions of “The Little Englishman” Henry Reeves, and others. However, the entry of the United States into the conflict, which led to the expansion of the struggle with its military and economic power, would witness the islanders and Americans fighting together again — this time as a group, not individually — during the short period of time the confrontation lasted.

This is where someone who would later become very well-known in American politics enters the picture, eventually becoming president: Theodore Roosevelt.

As you say, the figure and the detachment that stand out in this fight are Colonel Teddy Roosevelt and the Rough Riders. Roosevelt and his men fought with courage and gallantry during their stay on the island in the two or three months that the conflict lasted.

Theodore Roosevelt was an assistant in the United States Department of the Navy and had the vision to create a volunteer corps for this conflict, and he presented his idea to his superior. Since his combat experience was very limited, Roosevelt suggested that a hero from previous battles and a friend of his should take command of this new unit, and he offered to be his assistant. His proposal was accepted immediately.

Roosevelt resigned his position in the department, and soon afterward, Colonel Leonard Wood and Lieutenant Colonel Teddy Roosevelt were reviewing more than 23,000 applications received from candidates interested in serving.

The disparate group that was hastily selected, now called the First United States Volunteer Cavalry, consisted of polo players, hunters, cowboys, Native Americans, and athletic friends of Roosevelt’s from his time at university. This heterogeneous and disorganized group of nearly 1,000 men gathered at a ranch in Texas, and the few career military men among the participants served as training officers for the rest of the volunteers, since the latter had no idea what military life entailed.

Among them was Captain Bucky O’Neill of Arizona, who was the mayor of Prescott, a marshal famous throughout the West for his victorious deeds against the Apaches and against bandits and murderers; another was Allyn Capron, who was, all in all, the best soldier in the regiment.

Roosevelt believed that he represented the ideal model of what an army officer should be. He was the fifth in his family to serve in the United States Army, and both his body and mind were perfectly equipped to perform his duties. Tall and slender, an exceptional walker and boxer, a first-rate horseman with good aim, he seemed what he was: the archetype of the fighting man. Both men commanded companies and were extremely respected and admired by their men for their fortitude and discipline.

A naval battle and a battle in the eastern part of the island were key to ending the Spanish-American War.

The Spanish-American War is considered, on the whole, a pathetically one-sided conflict. The American battleship “Maine” exploded in Havana Bay, supposedly due to a mine, and the United States declared war on Spain.

On May 1, 1898, Commodore George Dewey destroyed the Spanish fleet in two hours at the Battle of Manila Bay in the Philippines, and the capital was occupied by American troops in August.

While the Cuban Mambises fought on land alongside American volunteers and regulars, the Spanish fleet in the Caribbean under Admiral Pascual Cervera was in the port of Santiago de Cuba when it was discovered by the Americans. An army of regular troops and volunteers under General William Shafter, including Teddy Roosevelt and his Rough Riders, landed on the east coast of Santiago and slowly advanced toward the city with the intention of forcing Cervera’s fleet out of the harbor and onto the open sea.

Cervera was forced to withdraw his squadron shortly afterward and tried to escape westward along the coast. In the ensuing battle, their ships were immediately attacked by U.S. cannons, and all of them were quickly grounded, burning, or sunk. Their fleet was destroyed.

“In the capture of the San Juan hills, our forces numbered about 1,000 men against some 4,500 Spanish soldiers,” Roosevelt reported. “Our total losses were 1,071, killed and wounded.” Of the cavalry division of some 2,300 men, including officers and enlisted men, there were 375 killed and wounded. The Rough Riders also captured a multitude of prisoners.