Roosevelt and the Rough Riders at S.Juan Hill, Cuba (XIX0009)

San Juan Hill, 1 July 1898: Roosevelt and the Rough Riders

The Battle of San Juan Hill was the largest engagement of the Spanish-American War and the one that made a future president. Theodore Roosevelt, who had resigned as Assistant Secretary of the Navy to raise a volunteer cavalry regiment, led the charge up Kettle Hill on foot after his horse became caught in wire — and spent the rest of his life describing the day as the greatest of his career.

The 1st United States Volunteer Cavalry

The regiment the press named the Rough Riders was assembled in weeks from an improbable mixture: Ivy League athletes and New York policemen who knew Roosevelt personally, alongside cowboys, ranch hands, Texas Rangers, prospectors and Native American scouts from the Territories. Colonel Leonard Wood commanded, Roosevelt was his second, and the unit trained at San Antonio before shipping from Tampa. Its horses never made it to Cuba: shipping space was short, so a cavalry regiment fought the war on foot.

Kettle Hill and the Heights

The assault on the San Juan Heights began badly, with American units backed up under Spanish fire from entrenched positions on high ground. What broke the deadlock was a combination of Gatling gun fire directed at the trenches and simultaneous pressure by the Rough Riders and the regular regiments — including the 9th and 10th Cavalry, the African-American Buffalo Soldiers, whose part in the assault was substantial and was consistently minimised in the accounts that followed.

What the Battle Actually Settled

Taking the heights put American artillery within range of Santiago and made the position of the Spanish fleet in the harbour untenable. It sortied two days later and was destroyed. Spain sued for peace within weeks, ceding Cuba, Puerto Rico, Guam and the Philippines. The war lasted ten weeks and transformed the United States into a colonial power — and Roosevelt, on the strength of San Juan Hill, into a governor, then a vice-president, then a president.

Giuseppe Rava’s Original Work

Giuseppe Rava reconstructs the Rough Riders as they actually campaigned: the brown canvas fatigue uniform, the slouch hat, the polka-dot neckerchief that became the regiment’s mark, the Krag-Jørgensen carbine. The tropical conditions and improvised appearance of the volunteer regiment follow contemporary photographs rather than later heroic illustration.

This is a limited edition fine art print, hand-signed by the artist, produced in SRA3 format on fine art paper. Ships worldwide.