Book: The Rough Riders

Overview
The Rough Riders is Theodore Roosevelt’s firsthand account of raising, training, and leading the 1st U.S. Volunteer Cavalry in the Spanish-American War of 1898. Written with brisk energy and vivid detail, the book moves from the regiment’s improvised birth to its campaign in Cuba, culminating in the assaults on Kettle Hill and the San Juan Heights outside Santiago. Roosevelt blends battlefield narrative with affectionate portraits of his men, offering a study in American voluntarism, leadership under fire, and the frictions between idealism and military bureaucracy.

Raising the Regiment
Roosevelt recounts resigning as Assistant Secretary of the Navy to help form a volunteer cavalry alongside Colonel Leonard Wood. The unit drew a striking mix: cowboys, ranch hands, sheriffs, Native Americans, miners, Ivy Leaguers, and athletes. In San Antonio, discipline and esprit de corps were forged through hard drill, marksmanship, and horsemanship. Roosevelt highlights a meritocratic ethic that cut across class and region, arguing that the diverse roster coalesced around a code of courage, initiative, and mutual respect. The press coined the nickname “Rough Riders,” and the men embraced it with pride.

From Tampa to Cuba
Mobilization at Tampa was chaotic. Logistics faltered, ships were scarce, and much of the regiment’s equipment and nearly all its horses were left behind, turning a cavalry outfit into an infantry force in everything but name. Roosevelt’s narrative dwells on the scramble for transport, the crowding aboard ships, and the heat and uncertainty of landing at Daiquirí and Siboney. He sketches the tropical environment as a formidable enemy itself, with swamps, jungle, and disease complicating every movement and amplifying the consequences of supply failures.

First Engagements at Las Guasimas
The regiment’s baptism of fire came at Las Guasimas on June 24, 1898. Advancing through dense brush against well-positioned Spanish regulars with smokeless Mauser rifles, the Rough Riders confronted invisible fire and steep ground. Roosevelt depicts confusion and improvisation, steadying the line under pressure while praising the grit of individual troopers and scouts. Losses were heavy, including promising young officers like Allyn Capron and well-known volunteers such as Hamilton Fish. The fight taught hard lessons about reconnaissance, fire discipline, and the deadly advantage of entrenched defenders.

Kettle Hill and the San Juan Heights
Roosevelt’s most famous passages describe the July 1 attacks. With supporting fire from Lieutenant Parker’s Gatling guns, the Rough Riders, regular infantry, and African American regiments of the 9th and 10th Cavalry surged against Kettle Hill. Roosevelt writes of leading from the front, rallying scattered units amid wire, brush, and crossfire, and seizing the blockhouse. Momentum carried elements forward toward San Juan Hill, where the combined pressure helped crack the heights. He memorializes the gallantry of men like “Bucky” O’Neill and underscores the decisive value of initiative, small-unit leadership, and inter-regimental cooperation.

Santiago, Sickness, and Home
After the heights fell, the campaign settled into trenches around Santiago. Heat, malarial mosquitoes, yellow fever, and inadequate rations, derided as “embalmed beef”, ravaged the ranks. Roosevelt details shortages of medical supplies, the endurance of exhausted troops, and the frustrations of command in a sickly camp. He became a leading voice calling for evacuation, helping draft a public letter urging removal of the army before disease consumed it. With the city’s surrender and the regiment’s muster-out, he turns to the bittersweet homecoming and the lingering bonds among veterans.

Portraits, Judgment, and Style
Throughout, Roosevelt sketches vivid character studies of Western cowboys and Eastern collegians alike, honoring steady privates as readily as famous figures. He praises the regular army and black regiments for professionalism and courage, while criticizing logistical blunders and complacent staff work. The prose is muscular, direct, and anecdotal, celebrating physical bravery and the democratic mixing of classes and regions. The Rough Riders stands as both a war memoir and a piece of nation-making mythology, shaping public memory of a brief, consequential war and the citizen-soldiers who fought it.