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This rare flag is an original reunion flag from one of the early Rough Riders Reunions, held annually between 1899 and 1904. The construction of the flag is of clamp-dyed wool bunting with a sewn cotton sleeve. The pattern, 8-8-7-7-7-8 is scarce on 45 star flags, but what makes the flag most special is the stenciled overprint for the veterans of the 1st U.S. Volunteer Cavalry.  The presence of the official unit name, the name of their most famous battle, and their informal name, "Roosevelt's Rough Riders", named for Theodore Roosevelt, the unit's famous leader and America's 26th President, makes the flag one of the most desirable military reunion flags one can hope to find.  Its relatively large size as a full-sized flag, rather than a small hand-waver parade flag, is unusual for reunion flags.  The fact that it shows signs of wear on the fly and evidence of repair, indicates that the flag was flown for some period of time by its original owner, likely as a point of pride, even after the reunion took place.

Theodore Roosevelt's Rough Riders are one of the most storied military units in American history.  The 1st U.S. Volunteer Cavalry mustered into service at the start of the Spanish-American War.  The unit was the only cavalry regiment to see action on the war, participating in the famed Battle of San Juan Hill.  Theodore Roosevelt's charismatic style and his daring and bold military leadership of the unit catapulted him to a national figure of legendary proportions. In August, 1898, as the unit was preparing to be discharged, the unit formed the "Rough Riders Association" with the intent of keeping the Rough Riders in touch after the war through reunions and other events.¹  The first reunion took place in 1899 in Las Vegas, followed in 1900 with a reunion in Oklahoma City, the 1901 reunion in Colorado, and 1902 in San Antonio, Texas.  Roosevelt attended these early reunions personally. Between 1905 and 1948, no official regimental reunions occurred, though informal reunions still took place. Just two years after forming the Rough Riders and fighting in Cuba in 1898, Roosevelt was nominated vice president on the Republican ticket headed by President William McKinley.  Upon McKinley's assassination in 1901, Roosevelt became the youngest sitting American President at just 42 years old. Roosevelt was likely serving as either Vice President or President at the time when this reunion flag was made.

¹ Roosevelt's Rough Riders, http://www.sharlot.org/buckey-oneill/182-roosevelts-rough-riders