Teddy Roosevelt
Just The Facts
- President of the United States of America from 1901-1909.
- Cowboy, soldier, historian, naturalist, rhinocerous hunter, author, bear hunter, explorer, elephant hunter, winner of the Nobel Damn Peace Prize, and the namesake for Teddy Bears.
- Agreed by all historians worth their salt to be the most badass politician in American history, world history, and the history of the universe in both fiction and non-fiction forms, possibly excepting Darth Vader. Possibly.
Early Life
Theodore Roosevelt, Jr., nicknamed "Teddy" or "TR", was born October 27, 1858 in New York City. As a young child, he was often sick and was stricken with asthma. Viewing this as a challenge, he proceeded to beat his asthma to death. In order to get exercise, he took up boxing as a kid. Coming from a rich family, he was eventually sent to Harvard.
At age 19, during his summer break, he went on hunting trip with logger William Sewell, who hired himself out to city folks who wanted to see the wilderness. Usually, they didn’t last more than a day or two. Sewell was astonished to find that not only did this NYC city guy joyfully canoe, hike, and hunt all day for weeks on end, but he actually enjoyed it more when they were soaked by rivers and nearly frozen to death by winds and cold.
During a boxing match at age 20, his opponent at one point punched him so hard he actually apologized. TR laughed it off, saying “Don’t mention it,” and went right back to the fight. (According to legend, the guy actually hit him after the bell sounded. When the crowd booed him, TR said that the guy didn’t hear the bell, then returned to fight.) You just couldn’t stop the guy from violencing things up.
At age 21, he took another hunting trip in the woods. Specifically, a winter trip in the Northeastern forests. After spending two weeks in literally sub-zero temperatures, he wrote in his diary, “I have never passed a pleasanter two weeks.” By contrast, Cracked staffers have been heard to start complaining when the air conditioning drops the temperature below 70.
And by the end of college, he entered into his Golden Years of love and joy when he married the love of his life, Alice Hathaway Lee, described by TR as “beautiful in face and form, and lovelier still in spirit.”
Out West
Four years later, his wife died in childbirth.
We know, this seems a pithy way of treating Alice Roosevelt, particularly since understanding so much of TR’s character rests in the death of his Love’s life at such a young age. TR himself wrote in his diary, “The light has gone out of my life.” Their charming courtship, and its quick, tragic end, forced him to be a tougher, harder man, a man with the power of a lion outside, but with a romantic sadness resting within. Like Mad Max, only with less leather bondage gear. Emotionally, for the rest of his life, he held a buried but potent emotion within his heart, and refused to mention
Oh, also, his mother died the same day. Total bogus, dude.
Alright, enough of that. Let’s get back to the violencing.
Distraught, TR moved out to the Badlands in the
Running into a grizzly is a situation known in hunting circles as “not good.” Given such a situation, TR, without hesitation, raised his rifle and shot the bear right between the eyes. First shot. No panicky shooting in his general direction, no turning and running, just a calm, quick, perfect shot. Thrilled by this adventure, TR started hunting Grizzly bears as a hobby. By contrast, on the last Cracked Staff hunting trip, upon arriving in the woods, six of us went into immediate Wii withdrawal, four went into a panic after seeing a squirrel run up a tree, one shot himself in the leg (twice) when a spider crawled over his boot, and three were never seen again.
Of course, in the Old West, bears weren’t the only killers. These were the days when the land was roamed by killers like Billy the Kid and Russell Crowe. It was a lawless time of violence and death, where a dispute over a card game resulted in knife wounds and lynchings, where the drunk outnumbered the sober, where a brothel was one of the more respectable joints in town, where walking down a street the wrong way could get you shot. So, pretty much just like modern-day Las Angeles, except with drive-by shootings replacing lynchings. The excuses for such violence were often thin and even non-existent.
One time, while TR was out hunting grizzlies, a local decided that the glasses-wearing, jolly-faced New Yorker shouldn’t be allowed to let his cattle graze on lands that nobody owned, and wouldn’t be a problem to get rid of. So, he hired a killer named Paddock to either scare TR out of town or shoot him out. Paddock went around town bragging about how he was going to kill the dude from

Of course, those from out of town didn’t always get right away that the jolly city guy wasn’t one of those guys you messed with. While TR was in a bar, a drunken gunslinger was waving his guns around and terrorizing the ladies in the bar before turning to TR and calling him “four-eyes.” TR responded, “If I have to, I have to.” He then punched the guy three times and crashed the guy’s head on the corner of the bar.
Historian and Politician
He also entered full-force into politics, getting appointed to the United States Civil Service Commission where he blah blah blah President of the New York City Police Commissioners blah blah destroyed police corruption blah blah Assistant Secretary of the Navy blah Governer of New York blah blah blah.
Let’s get back to the part where he kills things.
The Spanish-American War
Specifically, Spaniards.
TR was ready for some more fighting. “I should welcome almost any war, for I think this country needs one,” he remarked. As Assistant Secretary of the Navy, he had poured himself into preparing the US Navy for a war, and what was the point of all that hard work if it wasn’t going to pay off?
Fortunately for him, this was the 19th Century, a time when any old excuse would work for war. Heck, the French didn't even wait for excuses to declare war (and surrender) back then.
In 1898, the US declared war on Spain in order to free the Cubans. TR was thrilled and immediately rounded up a group of cowboys, Native Americans, and cops and whipped them into the 1st US Volunteer Cavalry Regiment, known as the "Rough Riders". TR became their Colonel, and led them into Cuba. Their charge up San Juan Hill became legendary.
The Cubans were now, finally, left free to rule themselves and create their own government. Really paid off, for both them and us.
Roosevelt's awesome victories made him immensely popular, and in 1900, he became the Vice President of the United States... for about six months, before President McKinnley was shot.
Now, for the first time in 40 years, the United States would be led by a man with the charisma, intelligence, moral center, and leadership to truly be one of the great leaders, a man who could accomplish anything, overcome any obstacle, lead through any difficulty.
So, of course, he became president in the one decade of the 20th century where absolutely nothing happened.






Makes you wonder why Chuck Norris jokes are a thing, not Teddy Roosevelt jokes.
ReplyNothing happened during that one decade of the 20th century, because nothing wanted to f**k with a decade where TR was in charge.
ReplyWow, wow, wow- As the police commissioner, he would wander the streets of New York at night and scour the city for cops sleeping during their shifts. He completely reformed the department.
Replyi think this should probably mention his friendship with Seth Bullock, aka the Sheriff from Deadwood.
ReplyI thought cracked was the internet shrine to Teddy Roosevelt's Engorged Manhood. This read like a wikipedia article with a mere sprinkling of humor.
ReplyWhat about the time he was giving a speech, got shot in the chest, then FINISHED THE SPEECH WITH A BULLET LODGED IN HIS TORSO
ReplyEdit: and the flagship of his fleet was named the "Big Stick"
Actually, the ship named "Theodore Roosevelt" is nicknamed "the Big Stick" by the ship's crew.
This had a lot of potential, but it was way too informative, with only the occasional joke thrown in here and there. Also, Bull Moose Party.
Replyhe also sent a fleet of battleships on a tour of the world looking for a fight ... kind of like those old wrestling matches where locals could see if they could last one round with one of the touring wrestlers.
ReplyThe whole Progressive movement happened. Fairly signifigant, actually.
Replybut not TR significant, not something he could really violence the hell out of