You've heard of the Rough Riders, Teddy Roosevelt, his Medal of Honor, and the ass-beating the United States gave Spain in Cuba. But do you know just how much went down on the Caribbean Island that day?


Let's start off with a big reveal: There's no reason the United States should have won in Cuba against the Spanish. With the exception of the Americans (especially Roosevelts' volunteers) being extremely hardy due to being raised in the rough backcountry of the American wilderness, the Spanish definitely had the upper hand.

Spain was in Cuba for centuries before the Americans invaded. They had hardened fortifications, strengthened over the years by repeated attacks from pirates, rebels, and conventional foes alike. Moreover, they were in the middle of putting down a slave uprising, so their troops were battle-hardened veterans. They also had better weapons, better food, and better gear.

By the time the Americans wanted to take the San Juan Heights (and Roosevelt charged Kettle Hill), the Spanish should have been ready to push the U.S. back into the sea.

But they didn't count on how difficult it is going up against America in what is, essentially, a home game.

1. The Rough Riders were mostly famous before leaving for Cuba.

That looks way too boring for TR.

Imagine the sitting Secretary of the Navy resigning his office to join a bunch of cowboys, Native Tribesmen, the sheriff of Houston, Robert Mueller, Baker Mayfield, Rafael Nadal, Michael Phelps, Malcolm Gladwell, and Sebastian Junger as they team up to finish Afghanistan off once and for all. That was, in essence, the Rough Riders.

2. They were woefully underprepared.

Pew... wait for it... pew

The Navy had no real way to land horses in Cuba and many drowned. Even when they did have horses, the Americans had to hack their way through the dense jungles to get anywhere they wanted to go. By the time Roosevelt got to Kettle Hill, he and his men had hacked all the way there. They also had only one black powder cannon and a few gatling guns, not to mention black powder rifles that gave away their position to the Spanish. They also were issued heavy wool uniforms to fight in Cuba in July.

The Spaniards, in contrast, had new Maxim machine guns and smokeless Mauser rifles.

3. Spain messed up.

It's helpful when the enemy comes to you. In the open. Wearing bright colors.

The Spanish commander, Arsenio Linares, didn't fortify the area where his gunners would have clear lines of fire to anyone mounting an assault. Instead, he fortified the top of the hill and his gunners couldn't necessarily see what the enemy was doing at the bottom.

4. Roosevelt was only supposed to move up in support

Nothing supports a battle like winning it.

T.R. and the Rough Riders were pinned down in high grass getting shot up by snipers on the nearby hill for hours before Roosevelt asked to advance and was told to only support regular Army troops attacking the front of the hill. Instead, he and his men charged the hill through the 3rd Cavalry, some of which joined them. Among the 10th Cavalry assaulting the San Juan Heights were the African-American Buffalo Soldiers, who joined Roosevelt in his charge up Kettle Hill.

5. One of America's greatest soldiers was there.

His leadership is how he earned his nickname.

A young Lieutenant John J. Pershing had to take command of D Troop when their captain was killed trying to breach Spanish defenses. He led the Buffalo Soldiers up the crest of the hill. One of Pershing's Buffalo Soldiers was the first to plant the Stars and Stripes on the hilltop.

6. Roosevelt almost lost the battle.

"Someone's watching the other hill, right? Right?"

Roosevelt bravely led the charge up San Juan Hill, an act which would earn him the Medal of Honor one day. But, in doing so, he left Kettle Hill lightly defended and subject to a Spanish counterattack. By the time Roosevelt realized what happened, 600 Spaniards were on their way to exploit his mistake. Luckily, the Americans moved Gatling guns to the crest of Kettle Hill by then and most of those attackers died.

7. It was not a flawless win.

Getting hit by giant caliber bullets is never fun.

The 1st Volunteer Cavalry suffered a 37-percent casualty rate, the highest of any unit in the entire Spanish-American War. Still the heights belonged to the Americans by 3 p.m. on July 1st. On July 4th, the Spanish fleet sailed out of the nearby harbor and met the U.S. Navy, which took down every last Spanish ship.

The war was over by mid-August, 1898, just six weeks later.