The Rough Riders – Some Things You Didn’t Know About Theodore Roosevelt’s Famous Volunteers


THE THREE-AND-A-HALF MONTH  Spanish American War  is one of United States’ least understood conflicts. But because of a 39-year-old New York bureaucrat-turned-soldier named Theodore Roosevelt, and his ragtag regiment of western cowboys, Indians, and East Coast swells known as the Rough Riders," an iconic moment from one of that war’s pivotal land battles remains forever etched in the American consciousness.

Of course, the Rough Riders weren’t the only unit to charge up Cuba’s San Juan Hill on a blistering July day in 1898. More than 8,000 officers and men of the U.S. Army’s Fifth Corps, both infantry and dismounted cavalry, including four regiments of African American Buffalo Soldiers,  participated in the Battle of San Juan Heights.    But it was Roosevelt and his Rough Riders, the media darlings of the war, who captured the public’s imagination. And they proved themselves to be as brave and steady in the heat of battle as the hardened veterans they fought alongside of.

Here are seven things you may not know about this fabled regiment of American adventurers and its extraordinary leader.

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 Colonel Theodore Roosevelt. 

Roosevelt initially turned down the command

Secretary of War Russell Alger offered Roosevelt, at the time the Assistant Secretary of the Navy, the colonelcy of the First U.S. Volunteer Cavalry.  But the future president doubted he had the experience necessary to lead a regiment. Instead, he requested that Alger appoint a close friend, Captain Leonard Wood,   to command the unit and that he be made lieutenant colonel. Alger did just that. But before the battle at San Juan, Wood was promoted to brigade commander, leaving Roosevelt to take charge of the Rough Riders. He was promoted to full colonel on July 11, 1898.


The Rough Riders drilling in Tampa. Ironically, the regiment would leave its horses behind in Florida. 

The Rough Riders walked into battle

Despite being a cavalry regiment, the Rough Riders went to war without their horses and would make their famous charge up San Juan Hill on foot. That’s because at the time the USV departed for Cuba, there was barely enough room aboard the transports to carry the 17,000 officers and men of the Fifth Corps, let alone their horses. Thousands of mounts had to be left behind; the Rough Riders were suddenly “doughboys.” In fact, four of the unit’s 12 troops were also forced to remain on U.S. soil. Despite the tight space aboard the ships, the officers did bring their own horses. Roosevelt’s two animals, Rain-in-the-Face and Little Texas, made the voyage, although the former drowned during the Cuban landing.

The Rough Riders charged up two hills at San Juan

The first enemy position the cavalry division assaulted on July 1, 1898, was Kettle Hill  — named for the large cast-iron sugar-refining cauldrons found there. Shortly after driving the Spaniards from their trenches on the summit, Roosevelt led several hundred dismounted cavalrymen, including a number of Buffalo Soldiers, in a charge on San Juan Hill, which faced them to the west. Running across the open ground under a withering fire from the Spaniards, he and his men captured a fortified house on the ridge-top (often confused with the famed San Juan blockhouse,   600 yards to the south, which was taken by the infantry).

A Colt revolver similar to the one Roosevelt carried up San Juan Hill.  

Roosevelt personally killed a man

Near the top of Kettle Hill, two fleeing Spanish soldiers fired on Roosevelt and his orderly missing them both. T.R. answered the fusillade with his pistol, his second shot “doubling up” one of the enemy riflemen. “Did I tell you that I killed a Spaniard with my own hand…?” he later wrote his friend, Republican senator Henry Cabot Lodge.   Amazingly, the revolver Roosevelt carried that day, a .38 caliber Colt Navy Model 1892,  had only recently been recovered from the wreckage of the USS Maine, the battleship that famously exploded in Havana harbour four months earlier – an accident that at the time Washington used to justify the war.

"The Scream of Shrapnel at San Juan Hill” by Frederic Remington. 

The unit suffered heavy casualties

In his after-action report of July 4, 1898, Roosevelt wrote that of the 490 Rough Riders he led into battle at San Juan, 86 were killed and wounded with another half-dozen missing. “The great heat prostrated nearly 40 men,” he added, “some of them among the best in the regiment.” From its formation in May to its disbandment in September, the Rough Riders suffered a 37 per cent casualty rate, the highest of any American regiment, cavalry or infantry, in the war.





Roosevelt and the Rough Riders stand triumphantly on the high ground commanding the field. 

Roosevelt won the Medal of Honor… 103 years later

In an official report on the Santiago Campaign, Lieutenant Colonel Arthur Wagner wrote: “In the assaults on Kettle Hill and San Juan Hill, the courage and energy of Colonel Roosevelt, of the Rough Riders, was so conspicuous as to command general admiration. There is no doubt that to the influence of his personal qualities the successful issue of the attack was largely due.” All of Roosevelt’s commanding officers recommended him for Medal of Honor,  including the Fifth Corps’ own major general, William Shaftner.  Amazingly, the War Department denied Roosevelt’s decoration. The colonel’s widely publicized reports about his men’s poor health while on campaign ruffled feathers in Washington and earned him the animosity of Secretary of War Alger. This wrong was finally righted in early 2001, when Roosevelt was posthumously awarded the Medal of Honor by President Bill Clinton  just days before leaving the White House.


                                                                     © Michelle Young 2012