4 True Stories That Prove Teddy Roosevelt Was the Toughest Person Ever

Teddy Roosevelt Was the Toughest Person Ever

Two-term president, victorious military commander, devoted conservationist. These are just a few of the hats that Theodore ‘Teddy’ Roosevelt wore during his lifetime. For the record, he was also a supreme badass who stared death in the face on many occasions and belly-laughed every time (literally, in one instance). Here are four of his most remarkable, death-defying adventures.

He took down an armed cowboy with his bare hands during a bar fight
By 1883, Teddy was already weary about politics; he had recently lost a bid to become the nominee for Minority Speaker of the House, so he decided to head West for a little R&R. He constructed a log cabin near Medora, N.D., which was designed as a frontier retreat from his New York City residence ― and what’s a frontier retreat without some frontier shenanigans?

One evening, Teddy was entering a saloon in the nearby town of Mingasville when a drunken patron fired several shots at him. The cowboy then pointed his firearm at Roosevelt’s face, mocked him with the term “four eyes,” and ordered him to buy a round for everyone in the establishment. Teddy responded by laughing in the man’s face, then charging him and beating him senseless. The cowboy fired one more shot at “four eyes”, which missed completely; Teddy then pounded the man’s head into the wooden bar until he was unconscious.

Once the fracas was over, Teddy hauled his would-be assailant to a shed and locked him up until morning, but not before he presumably uttered some macho line like, “Bar’s closed”, or, “I think he’s had enough.”

He navigated a frozen river to chase some boat thieves
Teddy spent the early months of 1886 at the Elkhorn Ranch, a North Dakota establishment located on the banks of the Little Missouri River. Roosevelt and his two hunting companions, Bill Sewall and Wilmot Dew, purchased a “clinker-built boat” to ferry them across the frozen river. After a particularly unfruitful hunting expedition one morning, the men returned to the river to find their vessel had been cut from its rope and taken to parts unknown. A normal man might have lamented the loss of the boat, but Teddy didn’t take kindly to theft.

So he, Sewall, and Dew spent the next three days building a boat from scratch. Once the makeshift boat proved navigable, the trio set off in search of the stolen clinker. Roosevelt’s account in his 1888 memoir, Ranch Life and the Hunting Trail, details a miserable pursuit:

“For three days, the three men navigated the icy, winding river among the colorful clay buttes hoping to take the thieves captive without a fight. A shootout was a concern, for Roosevelt noted that “the extraordinary formation of the Bad Lands, with the ground cut up into cullies, serried walls, and battlemented hilltops, makes it the country of all others for hiding-places and ambuscades.” However, Roosevelt was certain that the thieves would not suspect that he was in pursuit, for they had stolen virtually the only boat on the river. Roosevelt, Sewall, and Dow battled against the elements, too, enduring temperatures down to zero degrees Fahrenheit”.

They finally reached the trio of thieves, who were led by a man named Finnigan ― “a hard case” who “had been chief actor in a number of shooting scrapes”. Roosevelt and his men had little trouble overpowering the thieves and tying them up. But upon returning to the ranch with their quarry, they encountered an “impassable ice dam” that took them eight days to finally cross. Roosevelt entertained his freezing men and their bootless captives by reading from a copy of Anna Karenina that he brought aboard; by many accounts, he watched the men for more than 40 hours without sleep. When the party reached land, Roosevelt performed his duties as deputy sheriff and arrested the three men, rather than ordering them to be hanged ― a progressive legal decision, in those days.


He survived the hellish death trap known as San Juan Hill
One of Teddy’s most notable pre-presidential achievements came as commander of the Rough Riders, arguably the most famous U.S. regiment to see action during the Spanish-American War of 1898. The Riders’ legendary charge up Cuba’s San Juan Heights in Cuba (on foot, no less), led by a stalwart Lieutenant Colonel Roosevelt on horseback, was a pivotal victory for American troops.

All that stood between U.S. troops and the Spanish held-city of Santiago were two hills, San Juan and Kettle, which collectively formed the San Juan Heights. On the morning of July 1, the Rough Riders were ordered to attack the 760 Spanish troops who defended the two hills. Approximately 8,000 U.S. soldiers took part in the initial charge, but hundreds of men were killed by the time U.S. forces reached the base of the heights. Lt. Col. Roosevelt led the Rough Riders up Kettle Hill, aided by Gatling guns manned by his fellow Americans; they were joined by Captain Pershing’s 10th Cavalry, a black regiment who later became known as the ‘Buffalo Soldiers’. Under heavy Spanish artillery fire, the Rough Riders reached the crest of Kettle Hill and engaged in hand-to-hand fighting with the opposing army; the Americans secured their position on Kettle Hill when the Spanish began to retreat.

The men were sunburned and exhausted. But when Teddy saw Spanish troops firing upon the forces that had taken the adjacent San Juan Hill, he requested permission to assist them. Once General Sumner gave his approval, Lt. Col. Roosevelt led 500 men in a charge down the steep ravine that separated both hills. After wading through waist-deep trenches, the Riders successfully ascended the hill, drove away the lingering Spanish forces, and ended the day in firm control of the San Juan Heights. Surprisingly, it was not until 2001 that Teddy was posthumously honored for his actions in battle that fateful day.

Teddy was a popular president throughout his two terms in office,
He gave a stirring campaign speech… after being shot moments earlier
Teddy was a popular president throughout his two terms in office, which lasted from 1901 to 1909. But that’s not to say everyone loved him.

He decided to run as a candidate for the Progressive Party in the 1912 election against incumbent William Howard Taft (who had once served as Roosevelt’s Secretary of War) and Democrat Woodrow Wilson. On October 14, 1912, he was scheduled to deliver a rousing speech to a crowd in Milwaukee. Unfortunately, he encountered some trouble as he was greeting his supporters on his way to the podium. A saloon keeper named John Schrank approached Teddy, drew a pistol, and shot the former president in the chest. This would have surely been a fatal wound, were it not for Teddy’s crumpled, handwritten speech tucked in the breast pocket of his shirt; the document impeded the bullet, and Teddy only suffered a flesh wound.

Then, with the bullet fragments still lodged in his torso, Teddy took to the stage and delivered the speech as promised. When he produced the blood-stained paper from his shirt, he declared, “You see, it takes more than one bullet to kill a Bull Moose”, referring to his former political party. The address lasted for nearly an hour; after he stepped down from the stage, a woozy Teddy was rushed to a nearby hospital and treated for his gunshot wound. Wilson went on to win the election, but the Milwaukee incident cemented Teddy’s place in the Bad Ass Hall of Fame.