When we think of presidents and the American West, images of cowboys and vast landscapes often come to mind. But while some leaders were more “hat than cow,” Theodore Roosevelt truly lived the rugged frontier life. This remarkable chapter in American history saw TR, a Harvard-educated New Yorker, embrace the challenges of the Old West. It was here, far from city comforts, that the future president forged a deep connection with the land and its spirit, becoming much more than a politician—he became a man shaped by the wild.
After facing unimaginable personal tragedy, Theodore Roosevelt sought solace and strength in the untamed Dakota Territory. He wasn’t just visiting a ranch; he was building a new life, tending cattle, and immersing himself in the demanding rhythms of the frontier. These formative years weren’t just an escape; they were a crucible, transforming the young patrician into the resilient, “big stick”-wielding leader America would come to know and admire. Join Our American Stories as we explore how the raw beauty and harsh realities of the American West molded Theodore Roosevelt into the iconic figure who would one day lead the nation.
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Both were more hat than cow.
Theodore Roosevelt, on the other hand, owned two ranches and ran cattle in North Dakota and Montana. He was just forty-two years old when he took office in nineteen oh one, the youngest president ever. It was the West that molded Roosevelt into a man. Also, it was where he learned to carry a big stick. Here to tell the stories: Roger McGrath and Michael Blake. McGrath is a regular on our show, a regular contributor for the History Channel. Michael Blake is a two-time Emmy Award-winning makeup artist and a respected film historian.
Here’s McGrath and Blake.
Theodore Roosevelt was one of New York’s most accomplished, adventurous, self-sacrificing, and patriotic sons: Harvard graduate, author, cattle rancher, war hero, U.S. President, and the recipient of the Nobel Peace Prize and the Medal of Honor. He was a towering American figure whom sculptor Goodson Borglum carved into Mount Rushmore alongside Washington, Jefferson, and Lincoln, contributing mightily to making Roosevelt into the heroic man he became. Whereas days in the Old West. Unfortunately, most Americans today know little about Theodore Roosevelt and next to nothing about his life on the frontier. Theodore Roosevelt is born in the heart of New York City in eighteen fifty-eight, the second of four children to a prominent and wealthy family. Is not the sickly child often portrayed, but energetic and adventurous, although he does suffer from severe asthma attacks, which gives him a reputation for ill health. At eleven years old, he hides the Alps with his father stride for stride, and later it takes up boxing after being bumbled by two older boys. By the time he’s in his late teens, he is a robust, physical specimen, and his asthma attacks are less frequent. Roosevelt is home-schooled and proves a bright student and a voracious reader. He doesn’t attend one of the proper prep schools, as most young men of his social class do, but is nonetheless admitted to Harvard University at age eighteen. His father, whom he loved and admired greatly, tells him to take care of his morals first, his health second, and his studies third. He takes his father’s advice to heart and is a paragon a moral rectitude. Is also a top performer on the Fsity rowing in boxing teams. He excels in the classroom, graduating magna cum laude and Phi Beta Kappa, and finishes in the top twelve percent of his class. His achievement is all the more impressive because his father died two years earlier. From the inheritance Roosevelt received, he could have settled into a life of indulgence and indolence. Instead, he enters Columbia Law School in the fall of eighteen eighty, and nearly the same time he marries the love of his young wife, Alice Lee. After year at Columbia, the political bug bites him, and he’s elected to the New York Assembly. He’s in his second term when tragedy strikes. His wife gives birth to a daughter on February 12, eighteen eighty-four, but two days later, his mother dies of typhoid fever and his wife of kidney failure. The Bible blow leaves Roosevelt devastated for a time. He throws himself into political work with a vengeance, but soon decides to seek solace in the frontier West. Theora.
Roosevelt once said that if he hadn’t gone West, and hadn’t spent time in the Dakota Territory, he never would have been president. While some may say, “Oh, that’s typical hyper bowl of theater,” it’s actually very true. At the time, in eighteen eighty-four, he had lost both his mother and his first wife on the same day, February 14th, Valentine’s Day, within hours of each other. His first wife, Alice, had just given birth the day prior to their first child, who was also named Alice. So grief-stricken was he that he left the baby daughter in care of his older sister baby, and he went out West to a cabin he had recently bought and cattle ranch in what is now the area of Madora, North Dakota. Theodore went West to mend his broken heart, to escape. It’s kind of an interesting trait of Roosevelt. Whenever he lost something very important in his life went away, in this case going West.
Roosevelt first experienced the West on a hunting trip to Dakota Territory in eighteen eighty-three. He roughed it on several hunts and joined himself immensely. He also bought a ranch, the Maltese Cross, and stocked it with cattle. Now he is returning to the ranch, not for a visit, but to settle. These years in the West contribute mightily to shaping him into the man America will come to admire, a man who is part cattle-puncher, which helps make the cowboy a symbol of our country. Without his time and experiences in what was still the Old West, Theodore Roosevelt would not have organized the Rough Riders, not have led the charge up San Juan Hill, and not have become president.
And you’ve been listening to Roger McGrath and Michael Blake, the story of Teddy Roosevelt and what a story! Indeed, when we come back, more of this remarkable story here on Our American Stories.
Folks, if you love the stories we tell about this great Country, and especially the stories of America’s rich past, know that all of our stories about American history, from war to innovation, culture, and faith, are brought to us by the great folks at Hillsdale College, a place where students study all the things that are beautiful in life and all the things that are good in life. And if you can’t cut to Hillsdale, Hillsdale will come to you with their free and terrific online courses. Go to Hillsdale.edu to learn more. And we continue with Our American Stories and the story of Theodore Roosevelt and his time spent out West, healing and mending a broken heart. Let’s return to Roger McGrath and Michael Blake.
In June eighteen eighty-four, Roosevelt gets off the Northern Pacific Railroad at the town of Madora, founded only the year before by a French nobleman turned rancher, the Marquis de Moret, and named for his wife, at the western edge of Dakota Territory, near the border with Montana Territory. Madora is in the heart of the Bad Lands. Despite the name and its rugged terrain, the Bad Lands have thousands of acres of grasslands, especially in the valley of the Little Missouri River, where Madora and several cattle ranches develop. The area is still frontier. Only eight years earlier and two hundred miles to the southwest, Kester and two hundred men of the Seventh Cavalry were massacred at the Battle of the Little Pighorn.
When Theodore got to Madora area in eighteen eighty-four after the passing of his mother and wife, one of the first things he did within a day was he saddled up his favorite horse, Manitoub, and went out for a ride for three days by himself into the wilderness. He wanted to test himself. He wanted to see if indeed he could be like those who he had read about in earlier days of the Party pioneers, and he did quite well.
From Madora, tire Heads, seven miles south to the Maltese crossed to begin his life as a rancher. He is soon dressed in the buckskin suit made for him by one of the first white women to settle in the region, widow Mattox. He is armed with an ivory-grip Colt revolver and a Bowie knife. A wide-brimmed hat sits on his head when in the saddle. He wears spurs on the heels of his high-topped boots and steve pipe chaps. He writes his sister, “Well, I have been having a glorious time here and will hardened now. I have just come in for spending thirteen hours in the saddle. First and foremost, the cattle have done well, and I regard the outlook for making the business a success has been very hopeful. This winter, I lost about twenty-five add from wolves, called, etc. The others are in admirable shape, and I have about one hundred fifty-five calves. I shall put on a thousand more cattle and shall make it my regular business. I have never been in better health than on this trip. I’m in the saddle all day long, either taking part in the round of a cattle or hunting an antelope. This country is growing on me. It has a curious, fantastic beauty of its own.” Before the summer is out, Roosevelt lays claim to a large tract of land thirty-five miles to the north of the Maltese Cross, erects a cabin on it, drives in herd of cattle, and christens his new ranch, Elkhorn. When the Marquis hears about it, he says he has an earlier claim to the same property. Roosevelt notes the marquis has not built the cabin on the property or stocked with cattle, and ignores the Frenchman’s protestations. Roosevelt understands that not standing fast will expose him to ridicule as a weakling. He desperately wants to be respected as a man who lives by the Code of the West. Unwritten and informal, the Code of the West develops during the nineteenth century in the American West. First and foremost, a man is expected to stand his ground, to have sand in the face of death. Many a man expresses it simply, “I’ll die before all run.” A man is also expected to be loyal to his friends. The cowboys call it writing for the brand. A man is expected to work hard and pull his own weight. A man is never to steal another man’s horse. That isn’t mere thing left, but can mean a death sentence. For the man who is left without a horse. Certain forms of outlawry are tolerated. A highwayman can hold up a stagecoach or a train and take the express company’s treasure box, but he is not to rob the passengers. A man’s word is his bond. His word and his handshake are better than a legal contract. Women are to be treated with difference and respect. Roosevelt embraces the goat of the West and is determined to live by it. When he first arrives, many suspect he’s not up to it. “Will this scion from a prominent family in New York be up to the rigors of life on the frontier?” The glasses he wears don’t help. However, rows himself into working his ranches with such determination, energy, and stamina that even the most seasoned cowboys are impressed. But when faced with life or death, “Will he have sand?”
As a cattle operation, Theodore was the boss, and during roundups, Theodore would take a job just like any other cowboy, and he would do various jobs rounding up the cattle. The only thing he didn’t do was rope any of the cattle because of his poor eyesight. But he’d help in the branding and castrating the male cows and things like that. During one of the cattle roundups, Theodore was noticing that some of his men were lagging behind and the cattle were starting to spread out. So he yelled to them and said, “Yo that, hasten forward quickly now!” Well, the cowboys simply looked at him for a moment and thought, “What the heck was that?”
Now?
Most cowboys, when they round up cattle, they’ll do the various yahs or yehas, or whistles, or all sorts of sound effects to get them to move. Well, when the cowboys and Roosevelt’s outfit got a little bored, they would yell at the cattle, “Hasten forward quickly!” after that moment.
During his first summer on his ranches, Roosevelt is many miles west of the Elkhorn looking for stray horses. With the sun setting, he decides to ride to Mingusville, a town on the Montana side of the border with a small cluster of buildings including a railroad station, a livery, and a hotel. It’s dark by the time he stables his horse and walks towards Noolen’s hotel. Two shots suddenly ring out from the bar and dining room of the hotel. Undeterred, Roosevelt walks inside and finds the bartender and several men, as Roosevelt put it, wearing the kind of smile worn by men making believe to like what they don’t like. Roosevelt also sees a drunken patron with a revolver in each hand, swearing and strutting back and forth. A clock on the wall has two bullet holes in its face, evidence of the drunk’s prowess with his revolvers. When the drunk sees Roosevelt, he proclaims, “Four eyes will treat the house to drinks!” Roosevelt laughs along with everyone else, and takes a seat at a table, hoping that will be the end of it. However, the drunk strides over to the table and repeats the demand.
“You’re going to buy us a drink?”
And Theodore try to ignore it. And again he’s repeated his demand, with a few cusswords in it. And Theodore always said, “If it’s at all possible to avoid a fight of it,” he says, “But if you can’t, hit them, and hit them hard so they don’t get up.” Well, Theodore, the man’s standing in front of his table. Theatre is sitting down and he’s weaving, and Theodore said, “Well, if I’ve got to, I’ve got to.” And as he stood up, he pushed the table aside and hit the man with a sharp right to the gin, a sharp left, and another right, driving him back.
And you’ve been listening to Roger McGrath and Michael Blake tell the story of Teddy Roosevelt and his adventures out West. More of Theodore Roosevelt’s life story, his life out West and how it shaped him here on Our American Stories. And we continue with Our American Stories. And let’s pick up where we last left off with Theodore Roosevelt punching out a bully in a bar.
Here’s McGrath and Blake.
While clots into the floor, the drunk reflexively fires his guns, hitting no one. Roosevelt is ready to drop on the man with the knee of the ribs, but sees he’s unconscious.
Well, after this fight with the, uh, drunken cowboy, all the cowboys in the area of Madora respected Theodore. They accepted him then as one; he had proved his mettle.
Another incident that cements Roosevelt’s reputation as a man with sand and not just another Easterner, or playing cowboy. Occurs just after the ice breaks up on the Little Missouri River. In fear for their lives from vigilantes in Montana, three men steal Roosevelt’s boot that he tied to a tree just above the river’s shoreline on his Elkhorn ranch. When Roosevelt discovers the theft, he’s outraged. He and two ranch hands set out in a second boat to capture the miscreans. The thieves have a couple of days head start, but there are still ice foes on the river and the weather turns bitterly cold, forcing them to stop frequently, build the fires, and hunt for game. After a week of pursuit, Roosevelt, in his hands, see the stolen boat moored on the river bank and smoke coming from a campfire. They stealthily approach the campfire and see one man warming himself. Roosevelt springs out of the brush and levels at a Winchester. At the man, he offers; there’s no resistance, and taken prisoner. Still out hunting, his two partners returned singly and suffered the same fate at the hands of Roosevelt. Now in two boats, Roosevelt, his ranch hands, and the prisoners continued downstream until they come upon a ranch and secure a wagon from the rancher.
Well, Theodore didn’t want to sit with his back to these three men riding alongside the driver and the wagon, so he followed the wagon in ankle-deep mud in the middle of February, and he walked the forty-five miles to Dickinson to turn them over to the local law authority. And by the time he got there, his feet were almost frostbitten. He hadn’t slept for thirty-six hours because he kept he stayed awake the whole time to watch these guys so they didn’t try to escape when he turned him in the next morning, when they were arraigned in front of a judge who happened to be somebody Theodore knew from his days at Columbia College when he was studying to be a lawyer, and the judge’s name was Western Star. He asked the judge not to charge the German Man because he says, “I don’t think he knows what he’s doing,” and the German Man would profusely thanked Theodore for his efforts, and Theodore chuckled and said, “Well, that’s the first time I’ve ever been thanked for calling someone an idiot!” The other two men did get five-year terms, and he had the respect of the local cattle owners, but they didn’t understand why did you go to all that trouble when you could have just shot him or hung them, and that was it. And they didn’t understand Theodore. And this was something very key to Theodore’s make-up and something that would echo throughout the rest of his life, whether he was New York Police Commissioner or in charge of the Civil Service Board, or Assistant Secretary to the Navy, or the Governor of New York, and then ultimately the President of the United States. Theodore didn’t want vengeance. He wanted justice, and he saw justice serve. That was very important to him. Yes, it would have been easier to hang the three men or shoot them, but that was not what Theodore wanted. Obviously, if the men tried to shoot it out with them, they would have returned fire. But Theodore was determined to see these men brought to justice, and justice they.
Were even out West. The politician and civic duty is in Roosevelt’s blood, is instrumental in organizing the Little Missouri Stockmen’s Association, and at the organization’s first meeting eighteen eighty-four, he’s elected chairman or some call it president, and re-elected in eighteen eighty-five. In eighteen eighty-six, Madora’s newspaper, The Bad Lands Cowboy, says the association can congratulate itself on again electing Theodore Roosevelt as president. Under his administration, everything moves quickly forward, and there is non.
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