The year was 1883, seven years after George Armstrong Custer died at the Battle of the Little Bighorn and Wild Bill Hickok was shot from behind in a Deadwood saloon. It was just two years after the Earp brothers shot it out with the Clanton Gang at the O.K. Corral in Tombstone, Arizona, and only a year after Jesse James was assassinated in Missouri. Geronimo was still living free and raiding both sides of the border in the Southwest. The Wild West was not yet history when young Theodore Roosevelt determined to travel to the Dakotas and kill his first buffalo. After an almost comical series of mishaps, Roosevelt shot his bison, and, in the process, fell in love with the West. Before returning to New York, he invested in the Maltese Cross Ranch and ordered the construction of his first ranch log cabin.

Dressed in his custom-made buckskins, Roosevelt might have appeared to be a greenhorn in the Dakotas, but he was actually an experienced outdoorsman by his early 20s. His wealthy father had financed guided backcountry trips in Maine for Theodore and his brother, Elliott, where they learned to canoe, snowshoe, camp and hunt. The brothers had also traveled as far west as Minnesota on an extended hunting trip in 1880. He was an accomplished horseman, naturalist and taxidermist, and although he wasn’t the best shot due to poor vision, he had extensive experience with firearms.

After graduating from Harvard, Roosevelt married Alice Hathaway Lee in 1880 and climbed the Matterhorn while on their honeymoon in Europe. He was elected the youngest member of the New York State Assembly at 23 and subsequently the youngest speaker of the Assembly. Theodore and Alice shared a mansion in Manhattan with Roosevelt’s widowed mother. His successful start in life collapsed around him on February 14, 1884. On that Valentine’s Day, Roosevelt returned from Albany to his home in New York City to learn that his mother had died of typhoid fever. Later that same day, just two days after giving birth to their daughter, Alice died of failing kidneys due to Bright’s disease.

Broken-hearted, Roosevelt avoided all mention of his lost young wife and entrusted his infant daughter to his sister, Bamie. He would later write, “Black care rarely sits behind a rider whose pace is fast enough.” After putting his affairs in order, he made the four-day rail trip to Medora, North Dakota, and quickly immersed himself in the life of what he referred to as a “ranch man,” eventually being sworn in as a deputy sheriff and elected president of the local cattlemen’s association.

Roosevelt purchased a second ranch, the Elkhorn, across the Little Missouri from the Maltese Cross. He convinced two Maine woodsmen, Bill Sewall and Wilmot Dow, to travel west to manage his property. Over the next few years he would experience the epic lifestyle of the open range and grow into the man who would become a war hero and the 26th president of the United States.

In those days before widespread use of barbed wire, ranches on the northern plains were headquartered at key watering spots on rivers. The vast, surrounding federal land was considered open range where cattlemen were free to graze their herds. This necessitated a spring roundup to brand newborn calves, and a fall roundup to separate steers ready for market from the herd. All of the ranches would cooperate in roundups, and Roosevelt enthusiastically participated in these events complete with sleeping on the ground and meals from a chuck wagon.

The cowboy work of herding, roping and branding was exhausting, and Roosevelt often spent from sunup until sundown in the saddle. Nevertheless, he found time at night to work on notes for magazine articles that later became the basis for two bestselling books, “Hunting Trips of a Ranchman” and “The Wilderness Hunter.” While comfortable in the saddle, he never fully mastered the art of roping. His work ethic and grit, however, won him the respect and friendship of other ranch owners and cowhands alike.

Game was plentiful in the Dakota Badlands, and Roosevelt kept the ranch stocked with venison from mule deer, elk and pronghorn antelope hunts. Over the years, he would bag every species of big and medium-sized game in the West, including cougar, bighorn sheep, mountain goat and black and grizzly bear. On a hunt in the Bighorn Mountains, Roosevelt came face to face with a grizzly and felled it with a shot to the head from his custom Winchester Model 1876. The bear was in thick brush 25 feet from Roosevelt and his guide and ranch foreman, Arthur Merrifield, when the shot was made. Some of his western trophies are on display at Sagamore Hill National Historic Site, his former home on Long Island.

Taming The Badlands

As deputy sheriff of Billings County, Roosevelt took matters in hand when three thieves stole a boat used by his ranch hands to cross the Little Missouri. The culprits, led by Mike Finnigan, were reputed to be horse thieves and stock killers. Roosevelt tasked his foremen, Sewall and Dow, with quickly building a workable boat, and the three headed downriver to overtake the thieves.

They got the drop on the outlaws and spent the next eight days in harsh winter weather marching them back to stand trial for their crimes. Finnigan was surprised he and his partners were not immediately hung as horse thieves, and later wrote thankfully to Roosevelt from prison: “Should you stop over at Bismarck this fall, make a call to the prison. I should be glad to meet you.” While serving as a deputy sheriff, Roosevelt met and became lifelong friends with Seth Bullock, famed sheriff of Deadwood.

The namesake of the rail town of Medora was Medora Von Hoffman, the daughter of a wealthy New York banker and the wife of the Marquis de Mores. She was an excellent shot and hunted big game, including bears. The Marquis, a Frenchman, graduated from St. Cyr military academy and trained to be a cavalry officer. He was an accomplished swordsman and pistol shot, fighting successfully in several duels. He had the handlebar moustache and dark good looks of a Western villain straight from central casting. Utilizing his wife’s family money, he acquired 44,500 acres of Dakota rangeland in 1883 and built a slaughterhouse costing well over $6 million in today’s currency. His revolutionary plan was to slaughter cattle in Medora and ship the processed meat east in refrigerated rail cars, avoiding the weight loss of cattle shipped live to Chicago. He also intended to fence his land, making it impossible for smaller ranchers to water their cattle. Roosevelt had known Medora in New York and was on cordial terms with her and her husband, but he was destined to side with local ranchers in opposition to the Marquis’ plans to monopolize the cattle business.

The tension between the Marquis and the locals led to bloodshed when he and his employees engaged in a gunfight with three hunters. When the smoke cleared, Riley Luffsey was dead and the Marquis was charged with murder. While he was in jail awaiting trial, the Marquis heard a rumor that one of Roosevelt’s employees had spoken ill of him and encouraged his murder indictment. In a letter to Roosevelt, he asked, “Is this done by your order?” He ended the letter with a thinly veiled invitation to a duel by writing, “If you are my enemy, I want to know it…between gentlemen it is easy to settle matters of that sort directly.”

Ever the gentleman, Roosevelt had not conspired behind the Marquis’ back. He replied in writing, “Most emphatically I am not your enemy; if I were, you would know it, for I would be an open one, and would not have asked you to my house nor gone to yours.” He concluded by writing that he was “ever ready to hold myself accountable for anything I have said or done.” The matter went no farther, and the Marquis was later acquitted of the charges.

Trail’s End

The great blizzard of 1886 put an end to the Marquis’ plans and drove many cattlemen out of business. With as much as 90 percent of their cattle frozen in the storm, Roosevelt and others lost fortunes, and ranching forever shifted from the open range to fences and feed lots. Roosevelt returned east and resumed his political career, eventually leading the Rough Riders in the Spanish-American War and becoming president of the United States.

Today, Roosevelt’s ranches are preserved as part of the Theodore Roosevelt National Park, and the Marquis’ hunting lodge is the centerpiece of Chateau de Mores State Historic Site. Roosevelt’s experiences in the West inspired Owen Wister, a Harvard classmate, to write a classic novel about a heroic cowboy that was later made into a play and numerous movies, and gave its name to a television series. Wister dedicated The Virginian to his friend Theodore Roosevelt with the “author’s changeless admiration.”

Theodore Roosevelt’s Guns

As a “ranch man” in the Dakota Badlands, Roosevelt posed for photographs with a holstered Colt single-action revolver with ivory grips. He carried a .38-caliber Colt double-action revolver, salvaged from the battleship Maine, during the Spanish-American War. He reputedly carried a concealed early model semi-automatic pistol during his presidency, which is understandable considering he came into office upon the death of William McKinley at the hand of an assassin. The evolution of his sidearms from a single-action revolver to a semi-automatic is evidence that Roosevelt appreciated technological advances.

The .30-caliber Krag-Jørgensen was used by Roosevelt’s unit, the 1st Volunteer Cavalry, known as the Rough Riders, during the Spanish-American War. On his African safari after leaving the presidency, his arsenal included a 12-gauge Fox double-barreled shotgun, a .500-450 Holland & Holland double rifle and a .30-06 Springfield Model 1903.

His favorite firearm, however, was the Winchester lever-action rifle. He purchased the first of many Winchesters he would own, a Model 1876 in .45-75 with a custom pistol-grip stock, when he was 22. He wrote in “Hunting Trips of a Ranchman” that such a rifle “stocked and sighted to suit myself is by all odds the best weapon I ever had.”

Roosevelt cherished firearms and often presented them as gifts to valued friends, including a Winchester rifle he gave to Major General Leonard Wood, his old commanding officer from the Rough Riders.

This article was originally published in the winter 2018 issue of “American Frontiersman.” To order a copy and subscribe, visit

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