Tough Teddy and Old Hickory: America’s Most Badass Presidents

Tough Teddy and Old Hickory: America’s Most Badass Presidents

Khalid Elhassan - December 4, 2024

Theodore Roosevelt got into boxing in his youth, and continued to box well into middle age in the White House. He had to quit after a sparring partner permanently messed up one of his eyes. That was only one of the badass things about TR, but nothing as badass as Andrew Jackson. He didn’t box – he straight up killed up people in duels. Below are nineteen things about those and other fascinating Teddy Roosevelt and Old Hickory facts.

19. Badass Andrew Jackson

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Andrew Jackson. Andrew Jackson’s Hermitage

America’s seventh president, Andrew Jackson, was one of the toughest chief executives in the country’s history. Not necessarily a good person: as a general, Jackson had been too eager to hang his men for disciplinary infractions at the drop of a hat. He was also the only American president to have made his wealth primarily as an active wholesale slave dealer – a career considered disreputable even by many slave owners. However, one thing Jackson was good at was kicking ass and taking names.

18. A Serious Beef Against the British

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Andrew Jackson’s refusal to polish a British officer’s boots got him slashed with a sword. Andrew Jackson’s Hermitage

Andrew Jackson began his ass kicking career during the American Revolution, when he enlisted in his local militia at age thirteen. A year later, a fourteen-year-old Jackson defiantly refused to shine a British officer’s shoes. He got slashed with a sword across his face and hand as a result. That left the future president with a burning hatred of the British, and he paid them back in spades at the Battle of New Orleans in 1815. There, forces led by Jackson killed, wounded, and captured about 2500 British, while suffering only 300 casualties of their own.

17. Jackson, the Duelist

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Charles Dickinson. K-Pics

Andrew Jackson was prickly, readily took offense, and would just as soon kill you as look at you. When not leading men into combat or slaughtering Redcoats by the hundreds, Andrew Jackson could often be found out back dueling with somebody who had said something that annoyed him. Dueling, as in facing people with loaded pistols, taking aim, and opening fire at a given signal. And not once, or twice, but many times. The total number of Jackson’s duels is unknown, but estimates range from a low of thirteen to over a hundred. His most famous duel occurred in 1806, when he got into a tiff with a man named Charles Dickinson.

16. The Badass Who Discovered He Wasn’t as Badass as Andrew Jackson

Tough Teddy and Old Hickory: America’s Most Badass Presidents
An 1828 woodcut of the Andrew Jackson vs Charles Dickinson duel. Wikimedia

Charles Dickinson had a reputation as the best pistol shot in the country. That did not stop Andrew Jackson from calling him out. At the duel, Jackson stood stock still, and allowed Dickinson to take the first shot. Dickinson took aim, and put a bullet in Jackson’s chest. It wounded, but did not kill him. Jackson recovered, took aim, and pulled the trigger, but the pistol stopped at half cock. By the rules, that did not count as a shot. So as a horrified Dickinson waited, Jackson cleared the pistol, then took deliberate aim once more, and fired a shot that mortally wounded his adversary. As to Jackson, he recovered and went on to greater things, but Dickinson’s bullet remained in his chest for another nineteen years.

15. The Maniac Who Tried to Assassinate Old Hickory

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Andrew Jackson in 1824. Wikimedia

By the time he became president, Andrew Jackson’s dangerous reputation had been so well established, that only a madman would try to assault him. However, America never had a shortage of madmen. One of them became the first to attempt a presidential assassination when he took a shot at Jackson. Richard Lawrence, a house painter, often angrily muttered about Andrew Jackson. On January 30th, 1835, he was seen sitting in his shop, cackling to himself, before he suddenly got up and exited, with the exclamation: “I’ll be damned if I don’t do it!” The “it” was killing Jackson, which Lawrence tried to do by ambushing the president outside the Capitol building.

14. When Andrew Jackson Beat Up a Would-Be Assassin

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Andrew Jackson standing over his bludgeoned would-be assassin. Library of Congress

Richard Lawrence waited behind a pillar, and when Jackson passed by, took a shot at his back. The pistol misfired. Lawrence pulled out a second pistol and tried another shot, only to get another misfire. By then, Jackson had noticed what Lawrence was up to, and was understandably irate. There was no Secret Service presidential security detail in those days, so Old Hickory handled things himself. Although 67-years-old at the time – pretty old by the day’s standards – an enraged Jackson fell upon the much younger Lawrence, and proceeded to bludgeon him with his cane. The would-be assassin was probably saved from getting beat to death by people in the vicinity, who intervened to restrain the president and hustle Lawrence off into custody.

13. Teddy Roosevelt’s Sickly Childhood

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Teddy Roosevelt as a child – yes, boys wore dresses back then. K-Pics

America’s 26th president, Theodore “Teddy” Roosevelt (1858 – 1919), was a sickly child whose frequent bouts of ill health made his parents fear that he would never reach adulthood. The son of a Manhattan socialite and a businessman philanthropist father, young Teddy often suffered severe nighttime asthma attacks that defeated the remedies of America’s best doctors. As he described the bouts in later years, they felt as if somebody had sat on his chest and tried to smother him with pillows.

12. From Sickly Child to Health Nut

Tough Teddy and Old Hickory: America’s Most Badass Presidents
A young Teddy Roosevelt. Harvard College Library

A born fighter, Teddy Roosevelt did not despair. Instead, he discovered a means to help keep down the asthma, and simultaneously keep up his spirits: vigorous exercise. When he was around eleven-years-old, Teddy traveled with his family to Europe, and as they hiked in the Alps, the sickly kid discovered that he could keep pace with his father. It felt great, and from then on, TR adopted a regimen of strenuous exercise and outdoors activities. He also took up boxing to learn how to fight, after he got bullied by two older boys on a camping trip.

11. Teddy Roosevelt Was a Badass Boxer

Tough Teddy and Old Hickory: America’s Most Badass Presidents
A nineteen-year-old Teddy Roosevelt in Harvard. K-Pics

Teddy Roosevelt went to Harvard, where he boxed and rowed. He was good enough at the former to make it to second place in a boxing tournament. He also got into wrestling, judo, and jiu-jitsu. TR continued to practice martial arts until well into middle age, and kept at when he made it to the White. He was finally forced to stop in 1908, when a punch during a sparring session caused permanent damage to one of his eyes. After Harvard, TR spent a year at Columbia Law School, before he dropped out in 1881 to serve in New York’s State Assembly. His political career showed early promise, and he made a name for himself, especially with efforts against corporate corruption. Then came 1884, a truly terrible year for the future president.

10. A Heartbreaking Valentine’s

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Teddy Roosevelt’s diary entry for February 14th, 1884. Wikimedia

On February 14th, 1884, two days after she gave birth to their daughter Alice, Teddy Roosevelt’s wife died. His mother died a few hours later. The only entry on his diary that day was an ‘X’, and the notation “The light has gone out of my life“. That summer, he attended the GOP National Convention in Chicago, but his candidate lost. The personal and political setbacks in quick succession caused TR to feel burned out, so he decided to quit politics and move out West. He had visited the Dakota Territory in 1883 to hunt buffalo, and fell in love with the western lifestyle. So he invested $14,000 – a significant amount in those days – to become a rancher.

9. TR Out West

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Teddy Roosevelt’s Elkhorn Ranch. Theodore Roosevelt National Park

Teddy Roosevelt was more than just a rich East Coaster who went out west to play cowboy. In the summer of 1884, he established the Elkhorn Ranch on the banks of the Little Missouri River in the Badlands, about 35 miles north of today’s Medora, North Dakota. He enthusiastically embraced his new occupation as a rancher, and set out to learn the ropes – literally – of the profession. TR learned to ride, rope cattle, and hunt, and wrote three books about his experience. Later that year, he went on a days-long horseback ride to clear his head and take in the scenery, and eventually came across the Nolan Hotel in Mingusville, Montana.

8. When Teddy Roosevelt Walked Into a Seedy Bar

Tough Teddy and Old Hickory: America’s Most Badass Presidents
A bespectacled Teddy Roosevelt out West, on horseback. Theodore Roosevelt Presidential Library

The Nolan Hotel looked like a seedy dive, and Teddy Roosevelt was reluctant to enter – especially after he heard a pair of gunshots coming from the bar. However, nightfall was near, and it and it was cold outside. So he went in. He saw a “shabby individual in a broad hat with a cocked gun in each hand was walking up and down the floor talking with strident profanity. He had evidently been shooting at the clock, which had two or three holes in its face“. Soon as he saw TR, who wore glasses, the lout hailed him as “Four Eyes”, and announced to the bar that “Four Eyes is going to treat!” The future president tried to play it off as a joke, but the loudmouth followed him around.

7. TR and the Barroom Bully

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Teddy Roosevelt on horseback. Library of Congress

As Teddy Roosevelt described his encounter with an armed bully in a Montana bar: “As soon as he saw me he hailed me as ‘Four Eyes,’ in reference to my spectacles, and said, ‘Four Eyes is going to treat.’ I joined in the laugh and got behind the stove and sat down, thinking to escape notice. He followed me, however, and though I tried to pass it off as a jest this merely made him more offensive, and he stood leaning over me, a gun in each hand, using very foul language… In response to his reiterated command that I should set up the drinks, I said, ‘Well, if I’ve got to, I’ve got to,’ and rose, looking past him.” As seen below, things were about to get rough.

6. Making a Bully Come Correct

Tough Teddy and Old Hickory: America’s Most Badass Presidents
A bespectacled Teddy Roosevelt out West. Medora

Teddy Roosevelt put a serious beat down on the barroom bully. He continued: “As I rose, I struck quick and hard with my right just to one side of the point of his jaw, hitting with my left as I straightened out, and then again with my right. He fired the guns, but I do not know whether this was merely a convulsive action of his hands, or whether he was trying to shoot at me. When he went down he struck the corner of the bar with his head… if he had moved I was about to drop on my knees; but he was senseless. I took away his guns, and the other people in the room, who were now loud in their denunciation of him, hustled him out and put him in the shed“. The next day, the humiliated lout left town on a freight train.

5. When Teddy Roosevelt Got Shot

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Teddy Roosevelt campaigning in 1912. Historic Ipswich

Many of us get queasy or even faint at the sight of blood if we nick ourselves shaving, or suffer a paper cut in the office. Not so Teddy Roosevelt, who once gave a speech while bleeding from the chest, where he’d just gotten shot. It began in 1912, when TR came to regret his decision to walk away from the presidency in 1908. So he returned to the campaign trail, and ran for president as candidate of the Bull Moose Party. That October 14th, he made his way to a podium at the Milwaukee Auditorium, and opened with the unremarkable statement “Friends, I shall ask you to be as quiet as possible“. Next, however, he delivered one of the most remarkable lines ever uttered on the stump: “I don’t know whether you fully understand that I have been shot“.

4. Delivering a Speech With a Bullet in the Chest

Tough Teddy and Old Hickory: America’s Most Badass Presidents
X-ray of Teddy Roosevelt’s chest after he was shot. Business Insider

As Teddy Roosevelt’s horrified audience gasped, he unbuttoned his vest, to reveal a bloodstained shirt beneath. The former president then topped his previous statement with an even more memorable one: “it takes more than that to kill a bull moose!” TR pulled out a 50 page speech from his coat pocket, pierced through with a bullet, and continued: “Fortunately I had my manuscript, so you see I was going to make a long speech, and there is a bullet—there is where the bullet went through—and it probably saved me from it going into my heart. The bullet is in me now, so that I cannot make a very long speech, but I will try my best“.

3. “I Do Not Care a Rap About Being Shot

Tough Teddy and Old Hickory: America’s Most Badass Presidents
The attempt to assassinate Teddy Roosevelt. Shapel Manuscript Foundation

Just about any other candidate – except maybe Andrew Jackson – would have keeled over in shock or at least bid the audience adieu before rushing to seek medical care. Not Teddy Roosevelt. Assuring his audience “I give you my word, I do not care a rap about being shot; not a rap“, he went ahead and delivered a ninety minute fiery speech. The assassination had been attempted at 8 PM, as Roosevelt got into an open air car outside his hotel, and waved his hat at the crowd. Just then, the darkness was lit up by a flash from a .38 Colt revolver – TR had been shot.

2. TR Saved His Would-Be Assassin

Tough Teddy and Old Hickory: America’s Most Badass Presidents
Contemporary coverage of the attempt to assassinate Teddy Roosevelt. Library of Congress

An aide grappled with the would-be assassin and prevented him from firing another shot, before the crowd joined in to subdue the miscreant. The culprit, a mentally troubled Bavarian immigrant named John Flammang Schrank, would have been lynched on the spot if Teddy Roosevelt had not intervened: “Don’t hurt him. Bring him here. I want to see him. Roosevelt then asked Schrank “What did you do it for?” When Schrank stayed mum, TR instructed the crowd to turn him over to the police.

1.     A Deranged Assassin

Tough Teddy and Old Hickory: America’s Most Badass Presidents
The glass case and speech that saved Teddy Roosevelt’s life. Pinterest

Teddy Roosevelt reached inside his shirt and felt around. He encountered a dime-sized hole, and told an aide “He pinked me “. The former president then coughed into his hand a few times, saw no blood, and determined that his lung had not been pierced. He then directed that he be driven to the Milwaukee Auditorium, to address the waiting audience. The hefty speech, squeezed into his jacket pocket, had combined with a glass case and a dense overcoat to slow the bullet. It was later recovered lodged against his fourth rib, on a trajectory to his heart. As to the shooter, Schrank acted because of a dream, in which the assassinated president William McKinley had urged him to avenge him by killing his vice president and successor, TR. Schrank was found legally insane, and institutionalized until his death in 1943.

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Where Did We Find This Stuff? Some Sources and Further Reading

Davis, Burke – Old Hickory: A Life of Andrew Jackson (1977)

History Collection – 25 Reasons Why George Washington Was the Most Fascinating President in America’s History

Live Journal – Andrew Jackson, Man of Honor

Miller, Nathan – Theodore Roosevelt: A Life (1992)

National Park Service – Roosevelt’s Bar Fight

Smithsonian Magazine, November 2012 – The Speech That Saved Teddy Roosevelt’s Life

Thayer, William Roscoe – Theodore Roosevelt: An Intimate Biography (1919)

Wisconsin Magazine of History, Vol. 53, No. 4 (Summer, 1970) – The Attempted Assassination of Teddy Roosevelt

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