Teddy Roosevelt Historic Pistol Sells for $910K

By Rock Island Auction
Jan. 5, 2022

This revolver is one of the most iconic Smith & Wesson firearms in existence and is factory documented as shipped to one of the most beloved and influential men in American history: Colonel Theodore Roosevelt.

The included factory letter confirms this New Model No. 3 was shipped to “Colonel Roosevelt” on May 12, 1898, the same day Roosevelt left for San Antonio, Texas, and the same day as the bombardment of San Juan during the Spanish-American War.

On May 6th, Roosevelt had been officially sworn in as a lieutenant colonel in the 1st U.S. Volunteer Cavalry. He was previously expected to be in San Antonio around the 10th but was delayed, so the revolver was likely Texas shipped and was intended to be Roosevelt’s personal sidearm for the campaign in Cuba. On July 1, 1898,

Theodore Roosevelt famously led the Rough Riders in their charge up Kettle Hill during the Battle of San Juan Hill. The event became one of the most famous events in Roosevelt’s life and helped propel him to the governorship of New York, then the vice presidency, and ultimately the presidency in short order. He has remained one of the most iconic statesmen in our nation’s history, seen as the physical embodiment of American masculine values at the turn of the century, and was a highly influential leader during a significant transitional period in American history on many fronts.

For firearms collectors, veterans, and sportsmen, he is often remembered for his collection of beautiful firearms like this Smith & Wesson, his tough stance against foreign adversaries, his courage in combat, the sacrifice he and his family made for the country, his epic hunts both in the U.S. and abroad, his conservation of more than 230 million acres of public land for all Americans, the establishment of the Boone & Crockett Club and the American Bison Society, and so much more.

For historians, we can proudly call him one of our own; he published numerous books in his lifetime, including “History of the Naval War of 1812,” “The Rough Riders,”and the multi-volume “The Winning of the West.” He is the only American to be awarded both the Nobel Peace Prize (1906) and the Medal of Honor (2001).

There is something about Roosevelt for every American to admire. His contributions to this country are simply too immense to compile here. Roosevelt had many firearms, and they were often highly personalized special order pieces that fit his specific tastes and needs.


This revolver is chambered in .38 Long Colt, the standard U.S. service cartridge of the period. This caliber is very rare in the New Model No. 3 but makes perfect sense as a choice for Roosevelt as he was heading off to fight in the Spanish-American War. The factory engraving by the Youngs is also fitting given Roosevelt’s other engraved firearms. The embellishment is elegant and fairly understated rather than flashy, again fitting for an officer headed off to war. It consists of flourishes of scroll engraving with beaded backgrounds on the barrel, cylinder, and frame. The revolver has a pinned rounded blade front sight, notch rear sight on the barrel latch, “+SMITH & WESSON SPRINGFIELD, MASS. U.S.A.+” on top of the rib, Matching serial numbers are on the barrel, latch, cylinder, butt, and inside of the right grip. An early 20th century Rock Island Arsenal brown leather holster for a Colt double action service revolver with an “E.H.S.” inspector mark below the arsenal marking on the flap and “US” embossed on the body is included. These holsters were designed for the Colt Model 1892 and subsequent double action revolvers. A Model 1892 recovered from the USS Maine was famously carried by Roosevelt in the Battle of San Juan Hill. This iconic revolver won silver medal 352 for the Ten Best Arms Award at the NRA Annual Meeting in 1996 (medal and plaque included). It was on loan to the NRA National Firearms Museum c. 1998-2013 and then the National Sporting Arms Museum from 2013-2022.

The revolver has been featured in multiple publications. It has been featured in multiple editions of the “Standard Catalog of Smith & Wesson” by Jim Supica and Richard Nahas, including on the cover in 1996; in “Smith & Wesson Engraving” by Michael Kennelly on page 10; on page 277 of “Theodore Roosevelt: Outdoorsman” by R.L. Wilson; on page 4 of “Theodore Roosevelt: Hunter-Conservationist” by R.L. Wilson and discussed on page 111; in “Firearms, Freedom, and the American Experience Guidebook to the NRA Museum;” “Guns of the NRA National Sporting Arms Museum” by Supica, Wicklund, and Schreier on page 90 which notes “Roosevelt received this factory engraved revolver in May of 1898 just as he left New York for San Antonio to train the Rough Riders. It is one of only a handful of this model chambered for the then new .38 U.S. Service cartridge. It is believed he intended to take this revolver to Cuba in the Spanish American War.”; page 140 of “The Illustrated History of Firearms from the NRA Museums Second Edition” by Supica, Wicklund, and Schreier; and “The Colonel Roosevelt Smith & Wesson New Model Number Three Serial Number 32661” by Jim Supica in “The Texas Gun Collector” Spring 1998 issue. It was also featured for the month of September on Smith & Wesson’s 1995 calendar, the First Freedom NRA membership magazine centerfold in Feb. 2009 and on television on Ozarks Watch and CSPAN coverage of presidential firearms.

Also included are affidavits from Albert Brichaux and Jeffrey Allen Faintich stating that the revolver was sold by them to Jim Supica and guaranteeing that the revolver was originally shipped to Theodore Roosevelt. The statement by Faintich also states that Mike Berkshire of Palm Beach, Florida, “reported buying the revolver from the descendants of the bodyguard or valet of President Theodore Roosevelt, who had represented to Mr. Berkshire that the revolver had been a present from Pres. Roosevelt to their ancestor.” The revolver was then subsequently confirmed via a factory letter as having been shipped to Colonel Roosevelt. Berkshire sold the revolver in 1990. It was then briefly owned by Brichaux before being returned to Faintich to be sold to Supica.

Exactly where the revolver went after being shipped to Roosevelt is not clear aside from the fact that it later turned up in the possession of the family of a bodyguard/valet of Roosevelt who indicates Roosevelt had given the revolver to their ancestor. As explained in the provenance section above, this attribution was subsequently solidified when factory records confirmed the revolver was shipped to “Colonel Roosevelt.” What we do know is that in May of 1898, Roosevelt was in Texas preparing the Rough Riders to go to war. He was an early proponent of U.S. intervention in Cuba and of driving the Spanish Empire out of the Western Hemisphere considering U.S. involvement to be both advantageous to the country and also the honorable and just course of action. At the time, he was serving as Assistant Secretary of the Navy, but he desired to have direct involvement in the war and resigned to serve as an lieutenant colonel in the First U.S. Volunteer Cavalry, the soon to be famous “Rough Riders.” The unit was formed of men from many walks of life from both the East and West, but the recruits from the Southwest and Indian Territory gained a lot of attention and made up the bulk of the unit.

There were also New York policemen who had previously served under Roosevelt when he was the New York City Police commissioner and men from high society in the East. Some had fought in foreign wars in the service of other countries. American newspapers widely reported the affairs of “Teddy” Roosevelt and his “Rough Riders,” including Roosevelt’s planned arrival in San Antonio, Texas, around May 10th prior the revolver being shipped and then subsequent confirmation that he left on May 12th. His diary entry for the 12th reads, “Made for San Antonio,” and the entry for the 15th reads, “Reach camp at San Antonio.” While he never liked the “Teddy” nickname, he embraced the “Rough Riders” tag for his diverse troopers. He arrived in San Antonio on the 15th. After training in Texas, they departed to Tampa, Florida, at the end of May. Four of the companies stayed behind due to inadequate transports and some of the men died of malaria and yellow fever, but the rest arrived in Cuba on June 23, 1898. Many of their horses and mules had also been left behind, so the Rough Riders were forced to fight as infantry rather than cavalry. They fought in the Battle of Las Guasimas on June 24th and helped force the Spaniards to retreat. Soon, their most famous moment was upon them: the Battle of San Juan Hill. On July 1, the Spanish troops were heavily outnumbered, but they held the high ground, and the Americans were forced to charge exposed uphill to force them out. Roosevelt, the Rough Riders, the 3rd U.S. Cavalry, and the Buffalo Soldiers of the 10th U.S. Cavalry assaulted Kettle Hill on the right of the battlefield supported by suppressing fire from Gatling guns. They charged up the hill taking losses from both Spanish fire and the heat. The 10th Cavalry were the first to reach the top. Roosevelt moved to support the troops on San Juan Hill and then was ordered back to defend Kettle Hill which was soon counterattacked by the Spanish. The Gatling guns again proved significant in stopping the Spanish attack. Before the battle was over, 200 Americans were killed. Another 1,000 were wounded.

Though the various units had fought admirably together to take both Kettle Hill and San Juan Hill, the Rough Riders and Colonel Roosevelt received much of the attention along with the now famous Buffalo Soldiers. Roosevelt was posthumously awarded the Medal of Honor in 2001 for his actions. He preferred to be called Colonel Roosevelt after the war. He returned home to New York and then ran for governor as a Republican in 1898 and won, placing him at the head of the most populous state in the country at the time, but he soon jumped back to the national stage as vice president under President McKinley and then was propelled to the presidency when McKinley was assassinated at the Pan-American Exposition in Buffalo, New York. Thus, he went from a relative outsider to the leader of the Republican Party and the country.

As president, he was both popular and controversial. His dinner with Booker T. Washington at the White House marked the first time an African-American had been openly an equal guest at the White House and was met with serious hostility in the Democratic controlled South. He quickly earned a reputation as a progressive leader. Roosevelt established himself as a serious regulator of big business breaking up trusts and negotiating for better prices and pay, fighting corruption in government agencies, passing laws to ensure safer food and medicine, and conserving over 1/4 of a billion acres in National Parks, National Monuments, and National Forests and reserves preventing them from being destroyed and preserving the land for future generations, establishing himself as one of the foremost conservationists in American history.

After leaving the White House, Roosevelt and his son Kermit participated in the Smithsonian-Roosevelt African Expedition which is recorded in his book “African Game Trails.” During the expedition, they killed over 11,000 animals, including 512 big game animals, for preservation and scientific study back in the U.S. He then toured Europe. When he returned to the U.S., he clashed with President William H. Taft, his longtime friend and hand-picked successor, when Taft broke from Roosevelt’s progressive policies, particularly on conservation. The growing schism within the Republican Party led to Roosevelt running as the presidential candidate of the newly found Progressive Party in 1912. During the campaign, Roosevelt was shot in Milwaukee, Wisconsin. Despite being shot in the chest, Roosevelt went on to give his 90 minute speech, living up to his manly reputation after opening his speech with: “Ladies and gentlemen, I don’t know whether you fully understand that I have just been shot, but it takes more than that to kill a Bull Moose.” During his recovery, he noted “I’m fit as a bull moose.” Together these statements led to the Progressive Party being nicknamed the Bull Moose Party.

It was around the time of the assassination attempt that another revolver for Roosevelt was ordered. That Colt Single Action Army subsequently sold for $1,466,250 at Rock Island Auction Company on December 5, 2020. The split between the Republicans and the Progressives essentially threw the election to Woodrow Wilson and the Democrats. After his defeat, Roosevelt traveled to South America where he participated in the dangerous “River of Doubt” expedition aka the Roosevelt-Rondon Scientific Expedition. He planned to bring back examples of various animals for scientific study at the Smithsonian, but the expedition went poorly. Their boats were overturned losing supplies and their scientific specimens. Three members of the expedition died and nearly everyone contracted malaria. Roosevelt himself at one point asked to be left behind for dead as he languished from an infected wound on his leg as well as malaria, but Kermit would not leave his father behind. Though he made it back to New York, he never fully recovered his trademark vigor. Nonetheless, when World War I broke out, Roosevelt was authorized to raise volunteers but was stopped by President Wilson. His son Quentin served as a pilot and was shot down and killed.

Theodore Roosevelt died on January 5, 1919. Roosevelt’s last words were to his former bodyguard/valet, James E. Amos. He asked James to turn out the light and then died in his sleep. Vice President Thomas R. Marshall famously remarked, “Death had to take Roosevelt sleeping, for if he had been awake, there would have been a fight.” Unfortunately the identity of the specific bodyguard/valet that received this revolver was not recorded in the provenance documentation. Amos seems a very likely candidate and is known to have had one of Roosevelt’s revolvers in his possession after T.R.’s death. Amos was an African-American and began working for Roosevelt when he was president and was his valet for over a decade. His father was born into slavery and fought with the U.S. Colored Troops during the Civil War and was a Washington, D.C., police officer when he met Roosevelt while he was riding his horse. James was initially hired to help care for Roosevelt’s children but quickly moved up, including taking care of Sagamore Hill, and as valet/bodyguard during his presidency and became a close friend of the president and his family. He later worked as a private detective as well as for the U.S. Customs and the Interior Department, but remained in contact with the former president and returned to work for him. The Theodore Roosevelt Center noted Roosevelt called Amos “the best shot that I have ever seen” and indicated he “offered advice on Roosevelt’s gun collection and purchased and tested all of his firearms.” Amos was not with Roosevelt during the assassination attempt, but he was with him while he was recovering and helped nurse him back into health. The family called him to be at Roosevelt’s side during his final hours. Amos later wrote about his time with Roosevelt in “Theodore Roosevelt: Hero to His Valet” and went on to be one of the first and longest serving African American FBI agents, serving from 1921-1953. When Amos died, he left behind a variety of Roosevelt’s hunting trophies and other memorabilia to the Theodore Roosevelt Museum House. One page 151 of his book, Amos wrote, “While President he often went armed. I have in my home now a large revolver which Mr. Roosevelt placed at the side of his bed every night while in the White House. It was given me by Mrs. Roosevelt after his death.” Thus, this revolver very well could have been Roosevelt’s bed stand gun and have been given to Amos. Bedside use would certainly help explain how this revolver has remained in such extraordinary condition. Provenance: The Mike Berkshire Collection; The Jeffrey Faintich Collection; The Albert Brichaux Collection; The Supica Collection

Rating Definition:
Exceptionally fine. The revolver retains 85% plus of the original blue finish and has 80% bright original case colors visible on the hammer and slightly more subdued original case colors on the trigger guard. Wear is mostly limited to the muzzle, cylinder, and back strap where the revolver displays smooth gray and brown patina. The engraving and markings remain exceptionally crisp. The grips are very fine and have crisp checkering, attractive figure, and minimal minor handling and storage marks. Mechanically excellent. The holster is very good with mild wear. This incredible historic revolver is firmly documented by the factory as shipped to “Colonel Roosevelt” at the beginning of the Spanish-American War and, as such, is in a very exclusive class of presidential firearms. It has been on display in two of the most prestigious American firearms museums for many years and has been featured in multiple publications. Theodore Roosevelt remains one of the most admired presidents in American history, particularly to sportsmen and gun collectors, and thus this revolver is a true national treasure and will no doubt hold tremendous value for many years to come.
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