On Theodore Roosevelt’s 22nd birthday, he married his socialite sweetheart, Alice Hathaway Lee. Alice was the daughter of banker George Cabot Lee. She was a tall woman for the times, standing around 5’6”. She had wavy golden hair, blue-gray eyes, and people regarded her as strikingly beautiful. Her nickname was Sunshine because of her always-cheerful disposition. Roosevelt met Alice at a luncheon gathering in 1878 and was immediately smitten. He proposed marriage to Alice in 1879; she waited eight months before responding to his proposal. On the date of their marriage, Alice was 19 years old.
Alice and Theodore had a daughter whom they named Alice Lee Roosevelt, born on 12 February 1884. Two days later, Alice Hathaway Lee Roosevelt died from a condition called Bright’s Disease, a kidney dysfunction masked by her pregnancy. Eleven hours before his wife’s death, Roosevelt learned that his mother, Mattie, had died of typhoid fever. Completely distraught, Theodore left baby Alice in the care of his sister while he grieved. He resumed parenthood when baby Alice was three-years-old.
At the time, Theodore was a member of the New York State Assembly (1882, 1883, 1884). An idealistic young man, Roosevelt focused on corporate corruption, which included bribery to secure tax rate reductions of corporate income and judicial collusion. After Alice’s death, he threw himself into his legislative duties, almost ignoring the world around him. That he grieved mightily for Alice appears demonstrated by a diary entry: “The light has gone out of my life.”
Theodore visited the Dakota Territory in 1883. He wanted to hunt buffalo. He wanted to experience the life of a western pioneer. For several years, Roosevelt shifted back and forth between his home in New York and the Dakotas. Locals demonstrated little interest in helping the New York tenderfoot find his way. Roosevelt’s promise of quick cash convinced 25-year old Joe Ferris, a Canadian, to serve as Theodore’s hunting guide.
The hunting trip was not a pleasant experience. Roosevelt found the badlands exactly as Brigadier General Alfred Sully described them: “… hell with the fires out; grand, dismal, and majestic.” Roosevelt and Ferris encountered that terrible weather and a very rough trail. Through the challenge, Roosevelt displayed raw determination. Finding buffalo was difficult because, in 1883, buffalo were few and far between. While visiting with rancher Gregor Lang and using his small cabin as his base camp, Roosevelt became interested in raising cattle of his own. It seemed like a good investment because, with the extermination of bison on the northern plains, Texas cowboys were relocating large herds of cattle to the lush pastures of the Dakotas, Wyoming, and Montana. The Northern Pacific Railroad offered a quick route to eastern markets without long cattle drives, the effect of which reduced the quality of the beef.
Antoine Amédée Marie Vincent Manca de Vallambrosa, also known as the Marquis de Morés, was an entrepreneurial Frenchman and a key player in the North Dakota badlands. Morés was well known for his grandiose moneymaking schemes and his skill as a rifleman. The source of Morés’ wealth was his wife, Medora Von Hoffman, the daughter of a wealthy Wall Street banker. With Von Hoffman’s backing, Morés founded a meatpacking industry on the northern plain —his idea being to manufacture higher quality meat at lower consumer prices. Morés founded the town Medora, an area of about six square miles along the Little Missouri river bottom. He named it after his wife —its location intentionally placed near a lawless settlement as an insult to the rude settlers who lived there. In Medora, Morés built an abattoir, but the investment fizzled when Morés lost interest in it as he continued looking for new investments. It closed in 1886. But Morés initial enthusiasm for his scheme impressed Roosevelt and convinced him that cattle offered a sound business opportunity. Deciding to invest $14,000.00 in a cattle ranch, Roosevelt partnered with Ferris’ brother Sylvane and a man named Bill Merrifield, another Dakota cattleman. Yes, it was a business investment, but Theodore also wanted to live a western frontiersman’s lifestyle.
Between 1883-1885, Roosevelt shuffled between North Dakota and New York. He commissioned Ferris and Merrifield to build his Maltese Cross Cabin, but after 1884, he built a ranch named Elkton, 35 miles north of Medora. Roosevelt learned to ride horseback western style, rope, and hunt. He earned the respect of authentic cowmen, even though they were not overly impressed with the tenderfoot. On the other hand, he idolized the American cowboy because they possessed the stern, manly qualities “invaluable to a nation.” While in the Dakotas, Roosevelt wrote for national magazines describing the frontier; he also published three books: Hunting Trips of a Ranchman: Ranch Life and Hunting, and The Wilderness Hunter.
In 1886, when the ice on the Little Missouri River was beginning to break up, three no-goods cut Roosevelt’s skiff from its mooring at the Elkhorn Ranch and took it downriver. Roosevelt was determined not to let such men get away with his boat. It wasn’t much of a boat, but it belonged to Roosevelt (not the men who stole it)—so, there was an issue of pride —not only in refusing to allow anyone to steal from him but also because he was a deputy sheriff sworn to uphold the law. But to apprehend these men, Roosevelt (with his two ranch hands, men named Sewall and Dow) would have to place themselves at significant risk. Heavy ice jammed the river and spilled over its banks. Treacherous currents impeded river crossings, and the weather was viciously cold. He was also in pursuit of dangerous men, suspected rustlers, horse thieves, and cow killers.
The leader of this small band was a man named Finnigan, a red-haired, unshorn, smelly, and drunk much of the time; people also thought of him as a back shooter. Finnigan’s cohorts were a half-breed Indian and a crusty old German known for his viciousness in knife fighting. Finnigan’s reputation didn’t intimidate Roosevelt in the least. He took with him a camera by which he intended to record Finnigan’s capture on film.
Roosevelt and his men tracked Finnigan for three days, enduring sub-zero weather, inching their way along a winding river and through areas that were perfect ambush sites. The reward for Roosevelt’s watchfulness came on the third day of his tiring pursuit. A mid-afternoon, he discovered the stolen boat tied up along the shoreline and noted the wisp of smoke rising in the air from a nearby campfire. Only one of the men were in camp —the German standing guard while the other two hunted for food. When Roosevelt and his two men made their presence known, the German fellow gave up without a fight —mostly because his weapons were out of reach when Roosevelt, Sewall, and Dow rushed the camp.
Roosevelt and his men waited over an hour for Finnigan and his other man to return to camp. Their approach was noisy, unhurried, and unsuspecting. The Roosevelt party readied themselves. When Finnigan and the half-breed were within twenty yards, Roosevelt stepped out of the brush with his shotgun cocked and aimed. “Throw up your hand,” he ordered. The surprised half-breed immediately complied. Finnigan paused, assessed his situation, and then he too threw down his rifle. Because there was no rope to bind the men, Roosevelt ordered his captives to remove their boots. Should they try to escape, he reasoned, they wouldn’t get far without boots.
For another eight, miserably cold days, Roosevelt and his two cowboys transported the three thieves and their loot under guard. Danger followed the men as they made their way along the Little Missouri; Finnigan and his friends undoubtedly considered their chances for making a break and deserved a watchful eye but added to this were bands of Indians along Roosevelt’s path. While there was no indication of hostile Indians at this time, one never knew what an Indian would do. Roosevelt wisely chose to avoid the Indians, if possible.
By the time Roosevelt and his party reached the Diamond C ranch, they decided to split up. The plan was for Sewall and Dow to proceed downriver, while Roosevelt would march Finnigan and his men overland to the small town of Dickinson. No one at the Diamond C understood why Roosevelt didn’t just hang the thieves. Nevertheless, the rancher loaned Roosevelt a wagon to help transport the trussed-up thieves through ankle-deep mud. All the while, Roosevelt was cold, hungry, and growing very weary. After thirty-six hours of sleeplessness, Roosevelt reached Dickinson and turned his captives over to the county sheriff. In total, Roosevelt had journeyed 300 miles.
A few years later, realizing that had anyone else captured him other than Roosevelt, Mike Finnigan would have been strung up from the nearest tree, he wrote to Roosevelt and thanked him for keeping him safe.
While in the Dakotas, Roosevelt was prolific in organizing ranchers to address such problems as over-grazing. His work led to the establishment of the Little Missouri Stockmen’s Association. He promoted conservation around the Boone and Crockett Club. His ability to accomplish these things underscored Roosevelt’s stature among his western associates.
But the winter of 1886-86 was particularly severe, and it wiped out nearly everyone’s herd. Theodore, having lost over half of his $80,000.00 investment, returned to the East to resume his political life.
What we can say with certainty about Theodore Roosevelt, the born with a silver spoon in his mouth New Yorker is that as a child, he was weak and somewhat effeminate, a condition he worked steadily on to improve. In contrast to his youthful days, he returned to New York from the Dakotas physically and mentally tough. In this time, he also displayed his fearlessness. He would not back down from a fight, and he would not quit a difficult task.
It is worth considering Roosevelt’s cowboy life and its impact on what we know today about him and the old American west. Roosevelt was always a romantic man who perceived the American frontiersmen as exceptionally noble. They were men toughened by their experiences and their harsh environment. They were men accustomed to hard work, hardened by their circumstances, never giving up in the face of adversity. Such attributes were not only how Roosevelt perceived the western cowboy; it was how he saw himself. Better yet, it was a view of Roosevelt shared by those who knew him in the Dakotas —the cattlemen, his friends, and his neighbors (even though initially regarded as something of a dandy with four eyes).
The initial impressions of Roosevelt (whom the stockmen called Roosenfelder) changed after an incident in Montana in 1885. Theodore had been out searching for stay cattle. It was at the end of the day, and Roosevelt was tired and hungry. While taking a meal at a local saloon, a drunken cowboy derisively ordered Roosevelt, the four-eyed fella, to buy everyone at the bar a round of drinks. Roosevelt got up from his chair, whipped the cowboy from one end of the saloon to the other, and then returned calmly to his meal. The cowboy wasn’t aware that Roosevelt was a trained boxer. Roosevelt later described this cowboy, not as a bad man, only an “objectionable” bully and someone who deserved what he got. Word of this incident spread quickly, and, according to one account, Theodore went from being “four eyes” to “old four eyes,” and he was afterward “one of them.”
Roosevelt’s several books gave readers a clear picture of the noble cowman, notions later reiterated in the popular press. Theodore Roosevelt became the cowboy he most admired, and these were traits his eastern friends came to admire most about him. A careful evaluation of Theodore Roosevelt will reveal no distinction between the old west cowboy and the man Roosevelt became through the rest of his life. He was direct, fearless, spoke well, and was sure of himself. In the language of his cowboy associates, “Roosevelt didn’t take backwater from anyone.” Importantly, Roosevelt became one of the Dakotans, evidenced by the fact that he wasn’t stuck up, and he willingly took on every task usually assigned to a ranch hand. When moving cattle, Theodore’s time in the saddle equaled that of any cowhand.
Roosevelt, the cowboy, made his public debut after returning to the east in 1884. New Yorkers who knew him before his western trip marveled at how much he had changed —physically and psychologically. In August 1886, when another war with Mexico was possible, the 28-year old Roosevelt offered his services to the Secretary of War and the territorial governor of the Dakota territories. However, the tensions with Mexico soon abated, and Roosevelt would have to wait another ten years to demonstrate his military competence —which is something he did by recruiting cowboys to serve in his Rough Riders regiment.
In Roosevelt’s campaign for gaining the nomination for mayor of New York City, he became known as the “Cowboy Candidate.” There may have been no greater enthusiasm for Roosevelt’s campaign than from his Dakota Territory friends. Cowboy candidate is not merely how the campaign manager billed him during the mayoral campaign; it is how people back east began to see him, as well. From that point on in his life, Roosevelt achieved a lasting image of a western cowboy and never hesitated to capitalize on it.
- Brinkley, D. The Wilderness Warrior: Theodore Roosevelt and the Crusade for America. New York: Harper Collins, 2009.
- Hendrix, H. J. Theodore Roosevelt’s Naval Diplomacy: The U.S. Navy and the Birth of the American Century. Annapolis: Naval Institute Press, 2014.
- McCullough, D. Mornings on Horseback: The Story of an Extraordinary Family, a Vanished Way of Life, and the Unique Child who became Theodore Roosevelt. New York: Simon & Schuster, 1981, 2001.
- Philips, D. W. The Letters and Lessons of Teddy Roosevelt for his sons: Profiles in fatherhood. Vision Forum, 2001
- Roosevelt, T. R. Hunting Trips of a Ranchman: Sketches of Sport on the Northern Cattle Plains. Putnam & Sons, 1885.
 BrigGen Alfred Sully (1820-1879) was a Union military officer during the Civil War and Indian Wars. Sully graduated from the USMA in 1841 and, like his father Thomas, was a painter of some repute. Commanding a brigade during the Battle of Fredericksburg, his superior relieved him from command because Sully failed to suppress a mutiny by New York’s 34th Regiment. Sully was later found innocent of negligence, as charged but was afterward relegated to serving in the American West.