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Theodore Roosevelt Pocket Watch


It’s no secret that brands and individuals today are looking for that viral moment to ‘catch the wave’ hoping to fast track success—whether it’s a scripted plug or simply being noticed, which may lead to an article that catapults their idea, agenda, or product upward.

In 1898, the future 26th President of the United States, Theodore Roosevelt, caught a similar wave and yes, he earned it. That year, he helped organize and lead a cavalry regiment called the Rough Riders during the Spanish-American War. The Rough Riders are most famous for their charges, that Roosevelt urged, up both Kettle Hill and San Juan Hill while under heavy fire. The battles, known collectively as the Battle of San Juan Heights, were a pivotal moment in the Spanish-American War and contributed significantly to the U.S. victory over Spanish forces in Cuba. Theodore Roosevelt’s leadership during this battle, and throughout the war, earned him national fame and helped catapult him to the presidency in 1901.

Theodore Roosevelt’s sister, Corinne Roosevelt Robinson, and his brother-in-law, Douglas Robinson Jr., gifted him a pocket watch just before he departed for the Spanish-American War in Cuba in 1898.

Theodore Roosevelt Pocket Watch

Inside the watch, the inscription reads: “THEODORE ROOSEVELT FROM D.R. AND C.R.R.”

The watch is an American Waltham ‘Riverside’ 17-jewel Model 1888 (introduced in 1888) size 16 mechanical manual-wind silver pocket watch with a Hunter case designed to protect the watch’s face and crystal.

In 1898, Waltham employed thousands of workers who produced hundreds of thousands of watches annually. Waltham had one of the most advanced and largest watchmaking facilities globally, spanning several buildings in Waltham, Massachusetts.

Remember, at the time, men did not wear wristwatches as they considered them feminine. However, men would wear and display a pocket watch as it was much more than a timekeeping device; it was a powerful symbol of prestige, craftsmanship, and social status. And like today, a gifted watch could immediately become highly sentimental.

Roosevelt kept this pocket watch his entire life as it was a significant and cherished item—it accompanied him during the war, on his hunting expeditions in Africa, and while exploring the Amazon in South America. However, he owned and used multiple timepieces throughout his life, as was common for individuals of his status. His Rough Rider pocket watch was his treasure, but he also owned a beautiful pocket watch made by the prestigious American brand Tiffany & Co. With his extensive travel, he would have had access to many fine Swiss-made watches, railroad watches, and other gifted watches, including an Elgin pocket watch—a gift from his brother-in-law, Douglas Robinson, who played a significant role in developing the real estate market in New York City.

After Theodore Roosevelt’s death, his pocket watch, along with many of his other personal belongings, eventually became part of historical collections and exhibits. Specifically, this watch was part of the collection at the Sagamore Hill National Historic Site within Roosevelt’s home in Oyster Bay, New York.

In 1971, the watch was loaned out, first for a six-year term, later extended, to the Theodore Roosevelt Inaugural National Historic Site in Buffalo, New York. Museum staff typically conduct daily checks of exhibits to ensure all items are accounted for and in their proper place. During one of these routine inspections in 1987, staff on duty noticed the absence of the pocket watch from an unlocked case.

After detailed forensics and witness interviews by law enforcement, including the FBI, given the watch’s significant value and historical importance, the investigation remained ongoing as the mystery persisted.

That was until 2023, 36 years later, when the watch was discovered again. It turned up at a Florida auction house and was seized by federal agents after the auctioneer reached out to historical sites and the National Park Service. On June 27, 2024, the treasured watch was returned to public display at Sagamore Hill once again. A formal repatriation ceremony was held to mark its return to the National Historic Site, with representatives from the FBI and the National Park Service in attendance.