--- title: "How Teddy Roosevelt’s gun was as awesome as he was" date: "2021-07-10" modified: "2021-07-11" authors: - name: "Blake Stilwell" job_title: "Editor-In-Chief, Air Force Veteran" link: "https://www.wearethemighty.com/authors/blake/" url: "https://www.wearethemighty.com/popular/teddy-roosevelts-gun-was-awesome/" categories: - "History" - "Tactical" - "Weapons" --- # How Teddy Roosevelt’s gun was as awesome as he was ![]() In April 1990, the FBI was called to Teddy Roosevelt's house. No one would dare steal from TR while he was alive, but since he had been dead for 70-plus years and his house was long ago turned into a museum, the thief was able to rob the place and make off with an important piece of Americana: Teddy Roosevelt's piece. They stole the pistol he used at the Battle of San Juan Hill. To this day, no one knows who took it, and only the FBI knows who turned it in, but now it's back where it belongs. Its history is America's history, and the history of Teddy Roosevelt's sidearm matches the legacy of the man who wielded it. It started with a sinking ship. --- ![]() *In 1976, the Navy discovered the USS Maine was actually sunk by a fire that hit its ammunition stores, but let's not let the facts get in the way of a good story. (U.S. Naval History and Heritage)* In 1898, the USS *Maine* exploded in Havana harbor, a port owned by Spain at the time. Since anti-Spanish sentiment and pro-Cuban Independence was at a fever pitch among Americans at the time, the incident was blamed on a Spanish mine. Even an official Navy inquiry supported the mine theory. With more than 250 American sailors dead, the United States had to respond, and they did so by declaring war on Spain. Teddy Roosevelt was the Assistant Secretary of the Navy at the time. Incensed by the Spanish provocation, it wasn't enough for TR to just dispatch American warships to distant Spanish colonies. The man felt he had to go kill some Spaniards personally – and he did. He helped raise the 1st U.S. Volunteer Cavalry and deployed to Spain with an insane, ragtag group of cowboys, journalists, and athletes, the likes of which the world will never see again. ### Also: [7 cool facts about the Battle of San Juan Hill]() ![]() *Someone should have told Spain that white was a bad choice of uniform color.* Roosevelt earned a Medal of Honor for leading what was supposed to be an overmatched support column on a daring charge up the hill that totally routed the defending Spanish, and he did it wielding a Colt Model 1892 Army and Navy double-action, six-shot revolver, one special to Roosevelt for many reasons. First and foremost (maybe?), it was a gift to him from his brother-in-law, U.S. Navy Capt. William Sheffield Cowles. Where Cowles acquired it makes it really special: [the weapon was salvaged from the wreckage of the ]()[USS *Maine*]() in Havana Harbor just a few months prior to the battle. ![]() *You can't spell "counterattack" without the letters 'T' and 'R.'* The weapon is valued at over $250,000 and has an inscription above the grips: "From the sunken battle ship Maine" and "July 1st, 1898. San Juan. Carried and used by Col. Theodore Roosevelt." The April 1990 theft was actually the second time the pistol had been taken from Sagamore Hill. The first time was in 1936 when it was removed from the case, but the thief panicked and threw the weapon into the woods nearby. Roosevelt's sidearm and 1st Volunteers uniform are considered the most priceless artifacts on display at the museum. ## Author Blake Stilwell is We Are The Mighty's Editor-in-Chief, covering military news, entertainment, and history, along with veteran education, employment and entrepreneurship. He is a former U.S. Air Force combat cameraman with degrees in Graphic Design, Television and Film, International Relations, Public Relations, Business Management and Middle Eastern Affairs. After leaving the military, he began working in film and television production in New York and Los Angeles, work that included ABC News, NBC Olympics, and HBO Sports. He then spent two years in Washington with White House Communications, before joining the Near East Foundation. At NEF he served as an International Development Fellow, then Communications Officer, and finally, Media Officer for the Middle East and Africa. Based in the Palestinian Territory, he coordinated strategic communications between eight country offices, international media, and government and NGO partners. He began a career focused on writing and editing in 2015 with We Are The Mighty. He left in 2019 for Military.com, but returned as Editor-in-Chief in 2025. Blake’s work has been seen on CBS News, Fox News, CBC, The Chicago Tribune, Task & Purpose, Military Times, Recoil, Skillset, American History, and was shockingly even used in a Supreme Court argument. He is an avid traveler and small business owner in Ohio, where he spends most of his energy fixing up a very old house. ### Author social links [Facebook]() [Twitter]() [Instagram]() [LinkedIn]()