Possibly one of the finest and most historic gifts made by Roosevelt was a Winchester Model 1895, serial number 23576. As with most of all of his Winchesters, this rifle was embellished with a gold plate and was inscribed “To Leonard Wood, Governor of Cuba, 12-29-99 from TR.” At the time of the rifle’s presentation, Roosevelt was governor of New York and Gen. Wood had just accepted the stewardship of the island of Cuba as her governor. Wood was a career army officer and Medal of Honor winner who, in May of 1898, had accepted command of the 1st U.S. Volunteer Cavalry and was somewhat chagrined to find that his second in command was the former assistant secretary of the Navy, Theodore Roosevelt. However, during training in San Antonio and in combat in Cuba, Roosevelt proved himself to be an efficient soldier and inspiring leader. Wood felt confident, when he was called to accept a promotion at the divisional level, that Roosevelt could handle the command of the unit that was now affectionately known as “Roosevelt’s Rough Riders” by the press.

By nightfall of July 1, 1898, Roosevelt had led his men directly into the pages of the history books with their gallant charge up Kettle and San Juan Hills. Roosevelt’s charge won him a place on McKinley’s re-election ticket as vice president, as well as the Medal of Honor. (He was recommended for it in 1898, but due to politics it was denied him. The medal was finally awarded posthumously on January 16, 2001.) He gave his former commander an exquisite 1895 rifle as a token of his esteem when both men were governors.

Whenever Winchester introduced a new model, Roosevelt was quick to put it through its paces. He acquired an 1894 similar to all his other rifles in extras and embellishments and used it on an antelope hunt. His “little .30” as he called it, was able to knock down a good sized antelope at a distance of more than 180 yards. After witnessing the fantastic shot and the irrefutable and immediate results, his guide said that the gun was just “aces” in his book! He also used a Model 94 outfitted with a Maxim silencer at his Long Island home “Sagamore Hill” so as not to disturb neighbors when varmints were in need of culling.

Roosevelt’s deeds with his Winchesters are certainly the stuff of legend. You could hardly be expected to find a more colorful figure so strongly linked to something that is now, and in no small measure due to his patronage, considered a household word and so instantly recognizable. Once, while on a hunting trip, he led in the capture of three riverboat thieves with an 1876 Winchester at the ready. Another time while riding the perimeter of his ranch, he was set upon by a band of restless Sioux. One clear view of his Winchester across the saddle and they soon scattered. He would have been photographed holding a Winchester 1895 carbine atop San Juan Hill during the Spanish-American War had he not given it to another trooper in his unit who was without a rifle at the time.

A prolific writer, he authored hundreds of magazine articles and 39 books, six of which were about his hunting adventures. When it came to Winchesters he heaped praise upon them generously. His biggest and best publicized hunting expedition was the one he made to Africa with son Kermit in 1909-1910. Prior to the public announcement of his trip, Roosevelt’s personal secretary, William Loeb, sent the following letter to Winchester:

“To: The Winchester Repeating Arms Company

From: William Loeb, Jr.
Secretary to the President.

Date: July 16, 1908

Gentlemen:

The president is going to Africa ... .He probably has all the rifles he needs but his son has not. Before deciding what he will buy, the president would like to see your catalog ... Will you send your catalog to the President at Oyster Bay ... ?

Signed: Loeb”

Such a simple letter started a chain of events that resulted in dozens of exchanges via wire and mail over the next year concerning the rifles and equipment needed for the great expedition to Africa. Far from just wanting a few rifles for Kermit to have along on the safari, Roosevelt ended up having 15 wooden crates full of Winchester rifles, ammunition and spare parts for his expedition shipped by Winchester to his waiting steamer. Of the rifles, he choose the 1895 lever-action in .30-’03 U.S. as well as in .405 Win. to be the highlighted arms of the trip.

The 1895 Winchester was a departure from his standard taste in rifles. Designed by John Browning, the 1895 was the first Winchester to accept the new smokeless “hi-powered” rounds that were now revolutionizing the shooting world. With a tubular magazine being not only impracticable but dangerous as well when loaded with pointed bullets, Browning developed a rifle action with a box magazine that still allowed the user to get off quick successive shots that would hit harder and farther away with the new “hi-power” rounds. Roosevelt had seen the awesome effect smokeless cartridges had on battlefield tactics in Cuba in 1898 when his men were subject to withering fire from the new Spanish Mausers that used the smokeless powder. For Roosevelt, the combination of the fast working lever-action and the power the new sporting cartridges packed made the 1895 the perfect rifle.

Introduced in 1904, the .405 Win. cartridge was the most powerful round ever developed for a Winchester lever-action rifle. Roosevelt had to have not one, not two, but three 1895s in .405, and it proved very effective on almost every sort of game in Africa. The big 300-grain bullet was a hard hitter with an initial muzzle velocity of more than 2,230 fps.

In perhaps the best presidential endorsement of any product ever, Roosevelt wrote in Scribners Magazine: “The Winchester .405 is, at least for me personally, the medicine gun for lions.” He created a sensation for the gun that lasts to this day. The .405 was discontinued in 1932. However, rifles chambered in “Teddy’s” caliber continue to bring a high premium over examples that are chambered in a round still readily available. In 2000, Winchester announced the re-introduction of the Browning 1895 in .405 caliber, demonstrating that the spirit of “Big Medicine” is still alive and well.

To Winchester enthusiasts, and to all gun and hunting devotees, Roosevelt will forever be a heroic figure—the perfect example of the responsible hunter, sportsman and shooter. He was an authentic statesman who knew, understood and loved firearms. He comprehended what firearms represent not only to a free society, but to the future of conservation and the sustained use of natural resources.