Theodore Roosevelt: Leading the Rough Riders During the Spanish-American War

Included in McKinley’s call for volunteers had been an appeal for three regiments ‘to be composed exclusively of frontiersmen possessing special qualifications as horsemen and marksmen.’ Secretary of War Russell A. Alger offered command of the first such regiment to the administration’s only bonafide cowboy, Roosevelt, who had once operated a ranch in Dakota Territory. Roosevelt wisely declined because of his lack of military experience, suggesting that Leonard Wood be named colonel and that he go as second-in-command. Alger agreed.

The First U.S. Regiment of Volunteer Cavalry was to be recruited in the southwestern territories, with 340 men to be raised in New Mexico, 170 in Arizona, 80 in Oklahoma, and 170 from the Indian Territory. Within days of the sinking of the Maine, West Point graduate Alexander Brodie, a Prescott, Arizona, mining engineer, along with Phoenix journalist James McClintock and Prescott mayor William ‘Buckey’ O’Neill, had already begun recruiting volunteers.

The first to formally enlist was O’Neill, a frontier legend at age 38 and among the most popular men in Arizona Territory. Born in Ireland, he had come to Arizona in 1879. He was working as a journalist for the Tombstone Epitaph at the time of the O.K. Corral gunfight and soon had his own reputation for gunplay as the hard-riding sheriff of Yavapai County. His nickname came from his passion for faro, or ‘bucking the tiger’ in that frontier game. Dedicated to the cause of Arizona statehood, he was now prepared for the greatest wager of his life. ‘Who would not gamble,’ he wrote to a friend, ‘for a new star in the flag?’

Brodie secured an appointment as senior regimental major, with O’Neill and McClintock as company commanders. By May 4, 200 recruits were gathered in the Prescott plaza. Accompanied by Josephine, a rather ill-tempered young mountain lion given to the troops as a mascot by a local saloon owner, they boarded trains amidst much fanfare and set off for their San Antonio training station.

New Mexico Governor Miguel Otero wasted no time in recruiting troops and a remarkable corps of officers. Captain William Llewellyn of Las Cruces had been a federal lawman in Dakota Territory, famed for destroying Doc Middleton’s outlaw gang. Captain George Curry, the strapping former sheriff of Lincoln County, had known both Billy the Kid and Pat Garrett, while Captain Maximiliano Luna belonged to one of the most prominent Hispanic families in the territory. The New Mexico recruits reached San Antonio on May 10, joining the troops from Arizona and 83 men from Oklahoma raised by Captain Robert Huston of Guthrie. A week later, 170 more men arrived from the Indian Territory — including full or mixed-blood Cherokee, Choctaw, Chickasaw, Pawnee, and Creek Indians. Within days they were augmented by a remarkable contingent of about 50 well-to-do easterners. These Ivy League friends of Roosevelt included some of the best athletes and richest young men in America. The westerners initially viewed them with skepticism, and not a little contempt, but were soon won over.

‘These men are the best men I have ever seen together,’ Colonel Wood wrote to his wife, ‘and will make the finest kind of soldiers.’ Cowboys and polo players, teamsters and yachtsmen, lawyers and day laborers, lawmen and outlaws, miners and football players, Indians and Indian fighters formed a strange amalgam that forecast, in Roosevelt’s eyes, the new American century while harkening back to the old frontier. ‘Wherever they came from, and whatever their social position,’ he wrote, ‘[they] possessed in common the traits of hardihood and a thirst for adventure.’

Roosevelt did not arrive in San Antonio until May 15. He had remained in Washington to secure weapons, uniforms, and supplies for the regiment. The press had already dubbed the unit ‘Roosevelt’s Rough Riders’ — a name T.R. did not relish because of its obvious reference to Buffalo Bill’s Wild West show — and the men were anxious to see their namesake lieutenant colonel. Many were at first unimpressed with his somewhat comical appearance, but that quickly changed. Lieutenant Tom Hall sized him up immediately: ‘He is nervous, energetic, virile. He may wear out some day, but he will never rust out.’

Rumors abounded that Spanish Admiral Pascual Cervera’s Atlantic fleet was headed for either Puerto Rico or Cuba. On May 29, Commodore Winfield Scott Schley’s ‘Flying Squadron’ found Cervera moored in the harbor at Santiago de Cuba and set up a blockade. That same Sunday morning, the Rough Riders — 1,060 strong with 1,258 horses and mules — began boarding Southern Pacific Railroad cars for the journey to Tampa, Florida, their jump-off point for Cuba. ‘In all the world there is not a regiment I would so soon belong to,’ Roosevelt wrote to the president. ‘We earnestly hope we will be put in Cuba with the very first troops; the sooner the better.’

All was confusion in Tampa. Major General William Rufus Shafter, a Civil War veteran and former Indian fighter, was in command of the Fifth Army Corps. Weighing more than 300 pounds and afflicted with various ailments that did little to sweeten a notoriously foul temperament, Shafter was totally unfit to lead an expeditionary force into the tropics. In charge of his cavalry was the diminutive Alabama Major General Joseph ‘Fighting Joe’ Wheeler, famed Confederate cavalryman and current congressman. Ten regular and two volunteer cavalry regiments would be under his command. Despite his age and seeming frailty, Wheeler was as energetic and bold as Shafter was sloth-like and cautious. Brigadier Generals J. Ford Kent and Henry Lawton would command infantry divisions. In all, some 17,000 men were to embark for Cuba.