Lot 114

T. Roosevelt Cuba Signed Field Order Assuming Command of Rough Riders, 2nd Brigade. Highly Important and Historic!

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T. Roosevelt Cuba Signed Field Order Assuming Command of Rough Riders, 2nd Brigade. Highly Important and Historic!

Estimate: $8,000 - $10,000

Current Bid: $3,000

(4 Bids)

by University Archives
July 28, 2026 10:00 AM EDT
Live Auction
88 Danbury Road
Suite 2A
Wilton, CT, US 06897

Theodore Roosevelt
Camp Hamilton, Cuba, August 1, 1898
T. Roosevelt Cuba Signed Field Order Assuming Command of Rough Riders, 2nd Brigade. Highly Important and Historic!
DS

Theodore Roosevelt document signed assuming command of 2nd Brigade in Cuba. 1p, 8" x 10.5"; Camp Hamilton, Cuba; August 1, 1898. Manuscript Field Orders number 24 by which Roosevelt assumes command of the 2nd Brigade of the Cavalry, 5th Corps. Signed, "T. Roosevelt." Matted to an overall size of 11.5" x 14.25". From the collection of noted cavalry officer, Lt. General Harold G. Moore, Jr., whose heroic experiences were portrayed by Mel Gibson in the movie, "We Were Soldiers." Includes a statement of provenance from an executor of his estate. Letter has light dampstaining and wear along the flattened folds. Affixed to the mat along top only. An exceptional document recording Roosevelt's rapid rise to commander, a key moment that would launch his political career and his meteoric rise to the presidency less than three years later.

The Field Orders reads: "Pursuant to verbal order of the Division Commander of the 31st ult the undersigned hereby assumes command of the 2nd Brigade of the Cav Division 5th Army Corps."

The significance of this field order cannot be overstated. Only one assumption of command order exists to record the moment, and it is the very first order signed by the incoming commander, Theodore Roosevelt. As only a few presidents commanded troops in wartime, and Roosevelt's time in this post was brief, this document is an exceptionally scarce relic of his service.

Theodore Roosevelt helped form the 1st U.S. Volunteer Cavalry (famously known as the "Rough Riders") in the spring of 1898 at the outbreak of the Spanish-American War, serving as lieutenant colonel under Leonard Wood. Sent to Cuba with the cavalry division, they fought at Las Guasimas and then in the assault on San Juan Heights on July 1, 1898. On that day, Roosevelt famously led a charge up Kettle Hill, which made him a national hero. When Wood was promoted to brigade command, Roosevelt was made colonel of the regiment.

After the surrender of Santiago on July 17, U.S. troops were encamped in poor conditions, leaving the men exposed to malaria and yellow fever, including at Camp Hamilton where this field order was signed. During the very days he received verbal orders to assume command of the 2nd Brigade, Roosevelt joined in drafting and signing the famous "Round Robin" letter urging that the Army be brought back to the United States. The weather and unsanitary conditions in Cuba in midsummer needlessly put the troops at great risk.

Roosevelt's command of the cavalry brigade in Cuba lasted only through this immediate post-siege period. He and the Rough Riders sailed from Cuba on August 7 and landed at Camp Wikoff, Montauk Point, Long Island, on August 14, 1898, where they were quarantined and processed before being mustered out in mid-September.

This brief but dramatic Rough Rider episode (organizing the regiment, leading the charge at San Juan, and publicly demanding humane treatment for his men) brought Roosevelt national attention. Within weeks of returning home he accepted the Republican nomination for Governor of New York and won the election in November 1898. His successful term as governor propelled him onto the national ticket as Vice President in 1900. After President William McKinley was assassinated in September 1901, Roosevelt, still in his early forties, became President of the United States – less than three years from his time as a Rough Rider.

This field order is from the estate of Lt. General Harold G. "Hal" Moore, Jr. Moore was a brigade commander in the 1st Cavalry Division during the Vietnam War, making for a compelling custodial and thematic link between two iconic American cavalry brigade commanders. In recognition of his and his wife Julia's service, the Department of Defense renamed Fort Benning, Georgia, to Fort Moore from May 2023 through March 2025. A large body of Moore's papers and historic materials were donated to the National Infantry Museum and the General Hal Moore Military Museum, but this item was retained.

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: 14.25" x 11.5"
  • Medium: DS

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