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Teddy Roosevelt's Legendary Rough Riders

This cavalry regiment was celebrated for its role in the Spanish-American War.

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  • Colonel Theodore Roosevelt in his Rough Riders uniform on October 26, 1898.Photo Credit: Wikipedia

The Spanish-American War stemmed from the 1895 Cuban War of Independence, Cuba’s third war against Spain. The Cuban insurrectos had the support of many in the United States; Spain was the last European country to have American colonies, and Americans, barely 100 years removed from British colonization, could sympathize. There was perhaps no more fervent supporter of US intervention in Cuba than Theodore Roosevelt, who, along with the Rough Riders regiment he would command, exerted great influence on its outcome.

Born in 1858, Roosevelt grew up in the era of the Civil War, when battle hymns constituted popular music. His family was split along the Mason-Dixon line; he watched his mother Martha surreptitiously send care packages to the Confederate frontline, while his father Theodore Sr. paid a replacement to fight for the Union in his place. Theodore Jr.’s shame at his father’s inaction and his mother’s treason might have inspired his later obsession with proving himself in battle. 

After serving as a member of the New York National Guard, then of the New York State Assembly, then as New York City Police Commissioner, Roosevelt took up a position as the Assistant Secretary to the Navy. He was in that position when, on the evening of February 14, 1898, a sudden explosion tore apart the USS Maine, an American battleship docked in Havana to protect US interests. Of the 355 aboard, 260 lost their lives in the explosion and its immediate aftermath; six more later died of their injuries. 

Although the cause of the Maine’s sinking was uncertain, many were quick to blame Spain. Yellow journalism stoked the fire, and “Remember the Maine” became a pro-intervention rallying cry. Roosevelt and his friend Leonard Wood, surgeon to President William McKinley, flexed their government connections, encouraging intervention—and trying to secure themselves a place in the fighting when it broke out. They soon got their wish: on April 19, 1898, Congress passed a joint resolution calling for Spain to liberate Cuba. Spain declared war, and Congress soon responded in kind. 

Secretary of War Russell Alger offered Roosevelt command of a regiment of 1,000 volunteer cavalrymen. To Alger’s surprise, Roosevelt declined. Instead, he nominated Wood, a more experienced officer who had participated in a campaign against the Apache leader Geronimo. Roosevelt accepted a lieutenant colonelcy, becoming second-in-command. 

The original plan was to wrangle a regiment of Western warriors to staff the 1st US Volunteer Cavalry. Roosevelt and many of his contemporaries had been raised on Wild West shows, and believed in the mythic figure of the rugged, heroic cowboy. Roosevelt himself had found success as a dude rancher in the Dakota Territory. While the Volunteer Cavalry did count some dyed-in-the-wool prospectors, cowpokes, and cattle rustlers among its numbers, it also included Ivy League students, Roosevelt’s well-heeled New York chums, Native Americans, and tennis champions Robert Wrenn and William Larned. 

But gathered in San Antonio, Texas to be trained and equipped, all 1,060 Rough Riders got along swimmingly as they underwent horse drills, machine gun demonstrations, and rifle practice, often descending on the town for dining, drinking, and gambling after hours. They were surrounded by gawking throngs of onlookers, who snapped photos or clamored to buy the brass buttons off their uniforms. Roosevelt cozied up to reporter Richard Oulahan; when Oulahan quoted Roosevelt’s intention to organize a regiment of “rough riders,” the name stuck. Roosevelt had borrowed the nickname from Buffalo Bill, who called his traveling Western show "Buffalo Bill's Wild West and Congress of Rough Riders of the World."

The US had already scored a major victory against Spain in Manila Bay, and Roosevelt, itching for a fight, feared the war wouldn’t last. But on May 26, 1898, Roosevelt received a telegram from General William Shafter. The 1,060 Rough Riders and their 1,258 horses were to pack into seven hot, overcrowded trains and proceed to Tampa, where they would embark on a ship for Cuba. But the ships, too, were double booked, and there would be no room for the Rough Riders’ horses; they would go to Cuba as infantry. Thus Roosevelt’s Rough Riders became Wood’s Weary Walkers.

The men lacked sufficient rations on the journey, but they docked safely at the vacant village of Daiquirí. They had scarcely set up camp when they received their first orders: to attack the Spanish encampment at Las Guásimas, along with two cavalry units, including the all-Black 10th Regular. First, though, they’d have to trek through miles of thick, humid jungle. Many abandoned their packs along the overgrown trails. 

To make matters worse, the Spanish troops at Las Guásimas had fortified the area with trenches, and knew the trails well enough to surmise where the Americans would be marching from. They fired at the Rough Riders using smokeless gunpowder, leaving no visual cues to their positions. The foliage of the elm trees that gave Las Guásimas its name was too dense to see through, anyway, but their trunks were too thin to provide sufficient cover. The Rough Riders arrived at the battle late, but coordinated with other regiments to attack the trenches from two sides at once and eventually took Las Guásimas. 

Meanwhile, American scouts had reported an alarming sight from Santiago de Cuba: Spanish troops had been seen digging trenches into the hillsides surrounding the city, fortifying the ranch houses that stood atop them. On May 30, 1898, the Rough Riders received orders to march in that direction and wait in reserve for a coming battle. With those orders came the news that General Joseph Wheeler had come down with a fever. Brigadier General Samuel Sumner would replace Wheeler, Wood would replace Sumner, and Roosevelt would replace Wood as commander of the Rough Riders. 

teddy roosevelt's rough riders
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  • Roosevelt and his Rough Riders at the top of the hill they captured in the Battle of San Juan.

    Photo Credit: Wikipedia

The artillery regiments at Santiago de Cuba opened fire early. Spanish guns shot back, and Roosevelt was wounded in the wrist by an exploding shell. The Rough Riders, stationed near a fortified slope they’d soon dub Kettle Hill, took cover from the artillery, but were flanked by snipers. As casualties mounted, Roosevelt grew restless. Finally, orders arrived from General Sumner to ascend Kettle Hill.

Under heavy shelling, the Rough Riders charged forward in short bursts, periodically diving into the dirt to return fire. They slowly scaled the hill, Roosevelt following on his horse—until a fence near the summit forced him to dismount and proceed on foot. Spanish soldiers took cover behind enormous cast iron sugar kettles, but Roosevelt rushed them, dropping one with a revolver that had been recovered from the Maine. Kettle Hill was soon under the Rough Riders’ control, but in the distance, Roosevelt spotted another regiment inching its way up San Juan Hill. Never one to miss out on the action, he again cried out for a charge. 

Most of the Rough Riders were distracted or temporarily deafened by the constant boom of artillery, so only five of them heard the order. Roosevelt had to slink back and rouse the rest of his men; this time, they heard him loud and clear. The Rough Riders made a mad dash up San Juan Hill, stopping occasionally to return fire. The Spanish troops were entrenched, providing scant targets, but they were also woefully unprepared for such a direct assault. By 2:30 PM, San Juan Hill was under American control.

What followed was a protracted siege of Santiago de Cuba that lasted nearly two weeks, punctuated by mostly unsuccessful attempts at diplomacy. Save a few brief truces so negotiations could proceed, every day saw San Juan Hill shelled with artillery fire. Snipers were still an ever-present threat. Many of the Rough Riders had left their blankets in the jungle, and those who couldn’t find someone to share with were soaked by summer storms. Rations were scarce, the supply line was unstable, and canned goods spoiled quickly in the heat. Roosevelt was forced to dip into his own pocket to feed his men. Many contracted malaria and yellow fever, while others overdosed on the drugs they were issued to combat these illnesses. Field hospitals became overwhelmed, turning away anyone with a fever of less than 104 degrees.

Surrender finally arrived on July 14, 1898. The Rough Riders, who had suffered the most casualties in the battle of San Juan Hill (a fact Roosevelt would later recall with pride), had nothing left to do but wait to be paid and dismissed. 

The end of the Spanish-American war marked the beginning of an era of US interventionism. However, it didn’t come without significant casualties, many of whom were members of the Rough Riders. Talk of political advancement and a Medal of Honor for Roosevelt was already stirring when he returned to New York. In November of 1898, just months after his return, he was elected Governor of New York; three years later, he succeeded McKinley as President. He didn’t receive any commendations for his part in the war during his lifetime, likely owing to the media sensationalism around the Rough Riders and Secretary Alger’s disapproval of Roosevelt’s frankness about the poor conditions his men had faced in Cuba. Roosevelt was finally awarded a posthumous Medal of Honor in 2001—the first US president to receive one.