Along with serving two terms as the President of the United States between 1901 and 1909, Theodore “Teddy” Roosevelt also had a laundry list of supremely manly escapades throughout his life, such as the time he was shot in the chest in an assassination attempt, but went ahead and gave a lengthy speech he’d planned anyway before seeking medical attention. (More on this in the Bonus Facts below) Another such story he was often fond of telling came from his brief stint as a deputy sheriff for Billings County, North Dakota.

Originally Roosevelt only travelled to what were then the badlands of North Dakota to hunt buffalo in 1883, but the future president became so enamoured with frontier life and the beauty of the natural landscape that he decided to build himself a log cabin, buy a few cows and tend to the herd as a way of escaping the monotony of everyday life in New York City. Since we’re talking about Teddy Roosevelt, a man who never did things halfway, when we say he “bought a few cows” to serve his new hobby of ranching, we of course mean that he bought several hundred. These cows were left under the care of the Chimney Butte ranch, of which Roosevelt bought a considerable steak. (pun intended)

Roosevelt being Roosevelt reportedly loved being a cowboy and he threw himself into any and every job the ranch required whenever he visited.

When Roosevelt casually bought a few hundred more cows a year later in 1884, he established the Elkhorn Ranch so that he’d have a place to store them all. As for why Roosevelt doubled-down on his little ranching hobby, it’s believed it was as a result of the fact that Roosevelt’s wife, Alice, died of undiagnosed kidney failure shortly after giving birth to their daughter Alice in 1884. This was on the same day and in the same house that his mother died of typhoid fever, just 11 hours earlier. In response, he simply put a giant X in his journal and wrote one sentence under it: “The light has gone out of my life.”

Perhaps seeking escape, Elkhorn Ranch was born.

It was during his tenure as a rancher that Roosevelt also decided to try his grizzled hand at being a lawman, and although the post of deputy sheriff didn’t offer any pay save for remuneration on any travel costs incurred while on duty and a small stipend for any arrests made, Roosevelt nonetheless dedicated himself to this job with the trademark go-getting, no-nonsense attitude that would later become synonymous with his presidency.

In particular, Roosevelt felt that he had a moral duty to ensure criminals should receive a fair trial at the hands of the law and he was absolutely dogged in his determination when it came to pursuing those who’d committed any act of wrong doing, something he was only too happy to prove in March of 1886 when he was informed that the only boat on his ranch (and for many miles around) had been stolen. The boat in question was what Roosevelt used to cross the Little Missouri River to hunt and tend to his cattle.  According to Roosevelt,

We had no doubt as to who had stolen it; for whoever had done so had certainly gone down the river in it, and the only other thing in the shape of a boat on the Little Missouri was a small flat-bottomed scow in the possession of three hard characters who lived in a shack, or hut, some twenty miles above us, and whom we had shrewdly suspected for some time of wishing to get out of the country, as certain of the cattlemen had begun openly to threaten to lynch them. They belonged to a class that always holds sway during the raw youth of a frontier community, and the putting down of which is the first step toward decent government…

The thieves, who were described by Roosevelt as “a well-built fellow named [Michael] Finnigan“, “a half-breed, a stout, muscular man” called Burnsted and “an old German, whose viciousness was of the weak and shiftless type” called Pfaffenbach, had each been implicated in a number of crimes including cattle rustling, murder and, oddly less forgivable at the time, horse theft. The thieves had apparently stumbled upon Roosevelt’s boat while absconding from a nearby crime scene, reasoning that nobody could follow them down the river which was currently almost impassable due to a combination of a storm and severely icy weather resulting in much of the river being frozen.

Although the boat itself was of relatively little value, only being worth about $30 ($750 today), and the weather was dangerously bad, Roosevelt felt that by not pursuing the thieves, he would be ignoring his moral obligation as a lawman to pursue any criminal. Further, he reasoned,

In any wild country where the power of law is little felt or heeded, and where every one has to rely upon himself for protection, men soon get to feel that it is in the highest degree unwise to submit to any wrong…no matter what cost of risk or trouble. To submit tamely and meekly to theft or to any other injury is to invite almost certain repetition of the offense, in a place where self-reliant hardihood and the ability to hold one’s own under all circumstances rank as the first of virtues.

So as soon as he became aware of the theft, he called on his two most trusted ranch hands, Bill Sewall and Wilmot Dow and informed them that they were going to hunt the thieves down; a bold claim considering the thieves had stolen his only viable means of transport for such an endeavour and that the ranch was currently in the middle of an ice storm that had already killed 60% of the cows Roosevelt owned. Catching up to the thieves on horseback in that weather simply wasn’t an option.

Roosevelt and his companions spent the next three days building themselves a brand new boat with which to pursue the thieves down the icy river. Yes, Roosevelt built himself a new boat just to track down and arrest the men who’d stolen his other boat, even though it would be at great risk to his own life from the combination of the weather, potentially hostile Native Americans in the region, and that the men he was hunting were well armed and would have little qualms about simply shooting him and leaving his body where no one would ever find it.

Using his skills as an expert hunter, Roosevelt was able to easily track the thieves down river and find their camp, which he happened to stumble upon while two of the thieves were gone hunting. Given that the thieves had not expected any pursuit, having stolen the only boat for many miles around and that catching up by horse in that weather would have been impossible, they were lax, allowing his group to easily ambush the third member of the posse. As Roosevelt said, “The only one in camp was the German, whose weapons were on the ground, and who, of course, gave up at once…”

They then,

made him safe, delegating one of our number to look after him particularly and see that he made no noise, and then sat down and waited for the others. The camp was under the lee of a cut bank, behind which we crouched, and, after waiting an hour or over, the men we were after came in. We heard them a long way off and made ready, watching them for some minutes as they walked toward us, their rifles on their shoulders and the sunlight glinting on the steel barrels. When they were within twenty yards or so we straightened up from behind the bank, covering them with our cocked rifles, while I shouted to them to hold up their hands – an order that in such a case, in the West, a man is not apt to disregard if he thinks the giver is in earnest. The half-breed obeyed at once, his knees trembling for a second, his eyes fairly wolfish; then, as I walked up within a few paces, covering the centre of his chest so as to avoid overshooting, and repeating the command, he saw that he had no show, and, with an oath, let his rifle drop and held his hands up beside his head.

Rather than shooting or hanging the men on the spot, which he was entirely within his rights to do, Roosevelt vowed that each man would receive a fair trial.

Originally Roosevelt’s group had planned to float down river with the thieves to the nearest town, Dickinson, (going upriver wasn’t an option with the swift current) but this plan soon had to be abandoned as the river was simply too frozen over for the journey to be completed.  At first, they thought to wait it out to see if the ice would break up enough to again allow for travel. Roosevelt noted,

The next eight days were as irksome and monotonous as any I ever spent: there is very little amusement in combining the functions of a sheriff with those of an arctic explorer. The weather kept as cold as ever…. We had to be additionally cautious on account of being in the Indian country, having worked down past Killdeer Mountains, where some of my cowboys had run across a band of Sioux – said to be Tetons – the year before. Very probably the Indians would not have harmed us anyhow, but as we were hampered by the prisoners, we preferred not meeting them; nor did we, though we saw plenty of fresh signs, and found, to our sorrow, that they had just made a grand hunt all down the river, and had killed or driven off almost every head of game in the country through which we were passing.

Low on supplies, they decided to split up, with Roosevelt breaking off from the group so he could personally escort all three prisoners to the nearest town, on foot, before they ran out of food.

Since he was the only member of his party left, Roosevelt didn’t sleep for the duration of the almost 40 hour journey across partially frozen, occasionally “ankle deep”, sludge, reportedly keeping himself awake at night by reading Leo Tolstoy’s Anna Karenina while still pointing a shotgun at his prisoners so they couldn’t sneak away or kill him and then be happily on their way.

What makes this more impressive is that none of the prisoners were cuffed or bound in anyway during their transport. You see, the weather was so cold that Roosevelt was worried they would succumb to frostbite if he tied them up at night, so he simply decided to keep ever vigilant while escorting the three prisoners, who were no doubt looking for any opportunity to overpower their lone captor, the last stretch of the journey.

After travelling (from the start) some 300 or so miles across the roughest terrain imaginable in bitterly cold weather, Roosevelt was “most heartily glad when we at last jolted into the long, straggling main street of Dickinson, and I was able to give my unwilling companions into the hands of the sheriff. Under the laws of Dakota I received my fees as a deputy sheriff for making the three arrests, and also mileage for the three hundred odd miles gone over – a total of some fifty dollars.”

Roosevelt would later go on to write about this escapade in one of his many excellent books, Ranch Life and the Hunting Trail.

If you liked this article and the fascinating Teddy Roosevelt Bonus Facts below, you might also enjoy:

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• The Female Prostitute That Rose to Become One of the Most Powerful Pirates in History and Whose Armada Took on the Chinese, British, and Portuguese Navies… and Won

Bonus Facts:

• Roosevelt helped found the NCAA (National Collegiate Athletic Association), the Boone and Crocket Club, and the Long Island Bird Club; was one of the first fifteen people elected to the American Academy of Arts and Letters; was President of the American Historical Association and a noted historian himself; read thousands of books; wrote thousands of letters to go along with his books and thousands of magazine articles;  established 150 National Forests, 51 Federal Bird Reservations, 5 National Parks, 18 National Monuments, 4 National Game Preserves; successfully negotiated the end of the Russo-Japanese War (winning him a Nobel Peace Prize for this); reduced the National debt by about $90 million ($2.2 billion today or about 5% of the total national debt at the time); and oversaw the creation of the Panama Canal, among many other notable accomplishments.
• As mentioned briefly, Roosevelt was shot by saloon keeper John Schrank on October 14, 1912.  His life was saved thanks to a steel eyeglass case and his 50 page speech he was carrying in his jacket, both of which the bullet had to pass through.  His decision to go ahead with his speech, rather than seek medical aid immediately, was from concluding that because he was not coughing up blood, the bullet must not have penetrated that deeply into his chest.  His opening line for the speech was, “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.”  X-rays later showed that the bullet had lodged 3 inches into his chest and was embedded in his ample chest muscle.
• In a display of classic gentlemanly honorable behavior rarely demonstrated by politicians today, during the week Roosevelt spent in the hospital after being shot, the other two Presidential candidates stopped their campaigns until Roosevelt was released from the hospital and would be capable of campaigning himself.  This was even more significant as there were just two weeks left until the election.
• Theodore Roosevelt’s famous slogan “Speak softly and carry a big stick” was not his own invention, but rather a West African proverb that he particularly liked.  The full proverb is: “Speak softly and carry a big stick; you will go far.”
• After graduating college, Roosevelt saw a doctor about his frequent heart problems.  The doctor recommended that Roosevelt seek a career behind a desk and avoid any strenuous activities in his life.  Roosevelt obviously did not heed this recommendation, regularly boxing, playing tennis, hiking, rowing, playing polo, horseback riding, and practicing judo (earning third degree brown belt), among other regular exercises.  This actually probably helped extend his life, rather than shorten it, though he did eventually die of heart failure.  He also went blind in one eye thanks to boxing several times a week and in one instance having his retina detach after a punch to the eye.  After that happened, he decided to stop boxing and took up judo.
• Roosevelt frequently liked to skinny dip in the winter time in the Potomac River.
• Being the daughter of perhaps one of the manliest men of all time, Roosevelt’s daughter Alice was known for “unladylike” habits of smoking, gambling, promiscuity, late night parties, and keeping a pet snake. She also reportedly had a quick wit and was fond of constant rule breaking.  Roosevelt once commented on his daughter’s frequent practice of interrupting state meetings to speak with him, saying “I can either run the country or I can attend to Alice, but I cannot possibly do both.”
• When the Roosevelt’s moved out of the White House, Alice Roosevelt buried a voodoo doll of the new President’s wife, Nellie Taft, in the front yard.  Alice’s lone child, Paulina Longworth, was actually not from her husband, Nick Longworth, but the daughter of Senator William Borah who she had a long lasting affair with.  Nick Longworth himself may have had children by women not Alice, as he was known to have had numerous affairs throughout their marriage, which had become an unhappy one after Alice had campaigned against him.
• Roosevelt’s decision to get back into politics full time after living as a rancher may have never happened had it not been for the aforementioned severe winter of 1886-1887 where he lost nearly all of his cattle, as did most of the other ranchers in the region.  This was a total loss of about $80,000 in investments (about $2 million today) for Roosevelt.
• Roosevelt’s last name was commonly mispronounced even in his own day. He was even once publicly criticized for “mispronouncing” his own last name by Mr. Richard E. Mayne who was the chairman of the Department of Reading and Speech Culture for the New York State Teachers Association.  Mayne felt Roosevelt was “perpetuating a practice against which are set the principles of usage…” by pronouncing his name Rose-uh-velt rather than using common English pronunciation to pronounce it as it’s spelled.  As a response to Mr. Mayne, Roosevelt explained that his name is from his Dutch ancestry and so is pronounced as the Dutch would have.  Specifically, in Dutch the double “o” makes a long “o” sound, thus should be pronounced “Rose” rather than “Roos”.  And, indeed “roos” in Dutch means “rose”.
• Theodore Roosevelt was the fifth cousin of future President Franklin Delano Roosevelt.  He was also the uncle of Franklin D. Roosevelt’s wife, Eleanor Roosevelt, who was Teddy’s brother Elliott’s daughter.
• While Theodore Roosevelt’s father was a big supporter of Abraham Lincoln and the Union during the Civil War, his mother was on the other side of the fence.  She was from the South and from a slave owning family.  Her brother, James Dunwoody Bulloch, was a Confederate Navy commander.  Another brother was also a member of the Confederacy, serving as a midshipman on the CSS Alabama.  After the war, those two moved to England.
• How the Teddy Bear got its name was thanks to a specific hunting trip in Mississippi that Theodore Roosevelt took.  During the trip, Roosevelt and a group of hunters were hunting bear with little luck. After 3 days, their dogs found and old bear that they chased until exhaustion, then attacked.  The guides clubbed the bear, then tied it up and called for Roosevelt to come shoot the old and severely injured animal.  Roosevelt refused, claiming that it would not be sportsmanlike to shoot an animal this way and in this condition.  However, because the bear was grievously injured, he did eventually have one of the guides kill it to put it out of its misery.  The story likely would have ended here, except for Clifford Berryman, who was a political cartoonist.  Berryman made a cartoon depicting Roosevelt’s refusal to shoot the bear.  Morris Michtom, a shopkeeper, saw this cartoon and wrote to Roosevelt asking him permission to call toy stuffed bears his wife had made for selling in his shop “Teddy Bears”.  Roosevelt agreed to let him do this.  This name later saw a surge in popularity after a different company, Steiff, produced stuffed bears that were used as wedding decorations at Theodore Roosevelt’s daughter’s wedding.  These were called by those that covered the wedding and those at it “Teddy Bears”.
• Roosevelt was the first President to invite a black man to have dinner at the White House, Booker T. Washington.  This was after a meeting with Washington had run late, at which point Roosevelt invited Washington over for dinner.  About African Americans, Roosevelt had this to say, “…the only wise and honorable and Christian thing to do is to treat each black man and each white man strictly on his merits as a man, giving him no more and no less than he shows himself worthy to have.”
• While he was progressive when it came to black people and women’s rights, Roosevelt did not hold criminals, the sick or crippled, and others in such high favor, being in favor of eugenics (ironical considering his own long history of medical ailments).  At the time, eugenicists in the U.S. (and elsewhere in the world) were performing forced sterilization of the poor, sick, criminals, prostitutes, as well as forced abortions of pregnant women of ill repute or seen as inferior based on certain traits.  Roosevelt said of this, “I wish very much that the wrong people could be prevented entirely from breeding; and when the evil nature of these people is sufficiently flagrant, this should be done. Criminals should be sterilized and feeble-minded persons forbidden to leave offspring behind them.”
• This stance on eugenics was widely popular in the early 20th century, supported by such famed individuals as Winston Churchill, Margaret Sanger, H.G. Wells, George Bernard Shaw, John Harvey Kellogg, and, of course, Adolf Hitler, among many others.  This movement was spurred on and given its name by Sir Francis Galton in 1883, inspired by Galton’s half-cousin Charles Darwin’s work.  The eugenics movement started to lose its steam thanks to its association with the Nazi party.  That being said, numerous countries still performed forcible sterilization after the war, including the United States with the last forcible sterilization occurring in 1981. Sweden was another example of a country that kept the eugenics torch burning until 1975, forcibly sterilizing some 21,000 people and coercing another 6,000 into “voluntarily” being sterilized.  Sweden still controversially requires sterilization before sex change operations are allowed.  There are a surprisingly large list of countries that kept such programs going around this long or longer, more here
• Many think of Roosevelt as having been quite tall, but he was actually slightly short, particularly for a President.  He stood at just 5 feet 8 inches tall.  However, for much of his adult life, he was incredibly strong thanks to a regular regiment of heavy exercise.  Towards the end of his life, he did for a time become obese after being shot in the chest.  The aforementioned bullet was in too deep to get out safely, so was left in, causing him considerable pain for the rest of his life and stopping him from being able to do many of his normal exercises. He did lose a good amount of this fat while on his famous “River of Doubt” expedition where he lost 55 pounds after becoming severely ill with infection and “tropical fever”.
• Roosevelt injured his leg on the River of Doubt expedition after jumping from his own boat and attempting to stop with his own strength two of his crewman’s boats from crashing into the rocks.  This leg injury became infected and he soon also contracted “tropical fever”.  He attempted to get the rest of his expedition to leave him to die on several occasion, but they refused, despite his illness drastically slowing their progress; he needed constant medical attention was often delirious.  He never fully recovered from this, with the last decade of his life having frequent flare-ups of leg inflammation and various sicknesses as a result, as well as dealing with the pains from the bullet lodged in his chest.
• Roosevelt’s first known paper on zoology was written when he was just nine years old.  After spending considerable time researching and collecting insects, he wrote a paper called “The Natural History of Insects”.
• Along with taking a copy of Tolstoy’s Anna Karenina, Roosevelt also took a camera with him to document the capture of the criminals, for reasons known only to Roosevelt he never actually took any pictures and as a result had to stage pictures of the event using, interestingly enough, the very men who’d helped him capture the criminals as their stand-ins.
• Another favourite story of Roosevelt’s about his time as a cowboy was when he was accosted by a large man in a bar who tried to coerce him into buying a round for the whole bar. The legend goes that Roosevelt distracted the man by laughing before felling him with a punishing left hook – right punch combo.
• Even after Roosevelt became president, he was keen to cultivate his macho image, famously having his first official White House portrait, often playfully referred to his by his daughter as “the mewing kitten”, destroyed and repainted so that it made him look better.
• As noted, when Roosevelt first arrested the thieves, he could have quite simply shot each man where they stood without reprieve, something that actually came up when Roosevelt tried to secure a wagon while transporting the prisoners on his own and the ranch owner he spoke to asked him why he hadn’t just hung the prisoners as soon as he’d found them. By instead choosing to do the honorable thing, Roosevelt gained the begrudging respect of the gang’s ringleader, who later wrote to Roosevelt from prison thanking him for being such a peerless sentinel of justice. Roosevelt similarly refused to press charges against Pfaffenbach, stating that he didn’t “have enough sense to do anything good or bad.”, something Pfaffenbach was only too keen to thank Roosevelt for.