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There is no way Teddy should have come out alive.
San Juan Hill has become almost cartoonish in our historical imagination. The invasion itself is jeered at as a template for international imperialism, a model for every instance of American intervention. Theodore Roosevelt himself is sometimes portrayed as a borderline comedic figure.
None of that matters.
Military figures, those who actually serve on the battlefield, are regarded with a sort of awe by the rest of us, those of us who, because of circumstance, or luck, or connivance, have never seen combat.
It was by a strange combination of coincidences that a future President survived.
A nearby brigade was commanded by 4 senior officers within 10 minutes, as one after another was killed or carried away with life-threatening wounds.
Four commanding officers in 10 minutes.
American troops fully expected to meet an overwhelming force of thousands of Spanish troops as they charged toward the top of San Juan Hill. They had no way of knowing that 10,000 Spanish troops had been diverted, stationed as reserves in the city of Santiago de Cuba about a mile away. Nobody knows why General Arsenio Linares ordered them held back, away from battle.
So, instead of 10,000 enemy troops, Americans encountered fewer than 800. Most of those turned out to be inexperienced conscripts, newly drafted into battle.
American troops expected heavy fire from the big guns behind concealed Spanish fortresses. They had no way of knowing that those fixed fortifications were not laid out according to any military strategy. Instead, they were aligned in whatever direction geography made convenient. So heavy artillery could not be directed at the oncoming, completely vulnerable, Americans.
The central role of thousands of African American soldiers, and the loss of hundreds in battle, was nearly lost to history. And the point at which Roosevelt went from Kettle Hill to San Juan Heights is still uncertain.
What we do know for sure is that Colonel Theodore Roosevelt led troops into what they had to have thought was near certain death.
Quite a fellow, that Teddy Roosevelt.
Nobody knows what fueled the inner fire that led Roosevelt to physical bravery. The popular speculation was that he lived his life reacting to, and overcoming, the limitations of a sickly childhood. He had been stricken with such severe asthma that it had not been certain he would even survive into adulthood. He found his condition intolerable, and he overcame it with a combination of strenuous exertion and sheer willpower.
He was brave and powerful because he knew no other way to lead a life that he could tolerate.
Some have attempted to peer into the psyche of John F. Kennedy, speculating about what could have driven him into wartime danger. Like Roosevelt, it may have been a childhood of frailty. He was born pounds below a safe and healthy weight. He was stricken with one serious illness after another. At age three, deadly scarlet fever nearly killed him. A grim family joke came to be. If a mosquito bit young Jack, the mosquito would die.
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