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.