Description:

Theodore Roosevelt
n.p., ca. 1898
T. Roosevelt & Rough Riders, Incredible Photo! PSA Encapsulated
Photograph

Fantastic original Underwood & Underwood photograph authenticated and encapsulated by PSA/DNA as a Type IV, depicting Theodore Roosevelt and members of the legendary 1st United States Volunteer Cavalry, better known as the "Rough Riders" during the Spanish-American War in 1898. The sepia-toned photograph shows a group of uniformed men, some seated and some standing, posed on open terrain. The reverse of the photograph contains the original stamp of Underwood & Underwood, a prominent news photo agency of the era, and bears period wear consistent with an authentic turn-of-the-century press photograph. Slightly embossed stamp, but striking image. The photo measures 9" x 7" and is encapsulated to an overall size of 9.75" x 13.25."

The Rough Riders were a volunteer cavalry regiment formed in 1898 under the command of Theodore Roosevelt, who famously resigned as Assistant Secretary of the Navy to fight in the Spanish American War. Officially designated as the 1st U.S. Volunteer Cavalry, the unit achieved enduring fame for its daring charge up Kettle Hill, often mistakenly referred to as San Juan Hill, during the pivotal Battle of San Juan Heights in Cuba. The regiment was composed of an unusually diverse mix of men, including cowboys from the American Southwest, Ivy League athletes, Native Americans, and frontier lawmen. Their rugged image, combined with Roosevelt's bold and charismatic leadership, helped to forge a lasting national mythos around the Rough Riders as symbols of American bravery, toughness, and patriotic resolve.

This original press photograph is credited to Underwood & Underwood, one of the most influential photojournalism agencies of the late 19th and early 20th centuries. Founded in the 1880s, the company became a global leader in stereoscopic imagery and news photography, known for distributing high quality visual coverage of major events to newspapers and magazines worldwide. Their documentation of military campaigns, including the Spanish American War, played a significant role in shaping public perception of American imperial and military endeavors.

This item comes with a Certificate from John Reznikoff, a premier authenticator for both major 3rd party authentication services, PSA and JSA (James Spence Authentications), as well as numerous auction houses.

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  • Dimensions: Photo: 9" x 7" Slab: 9.75" x 13.25"
  • Medium: Photograph

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October 8, 2025 10:00 AM EDT
Wilton, CT, US

University Archives

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Bid Increments
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$2,000 $2,999 $200
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