By the time the Rough Riders faced off against the Spanish at the Battle of San Juan Hill, Spain had been occupying Cuba for years. The Spanish knew the terrain well and had spent years fighting off rebels, pirates, and other invaders.
An Interesting Turn of Events
Spain had a solid weapon, gear, and food supply, plus they had plenty of seasoned soldiers, especially since they had just dealt with an uprising amongst their slaves. Knowing this, it would have made sense for the Spanish to defeat Teddy Roosevelt and Rough Riders.
However, history tells us that is not how it went. Before heading to Cuba, the Rough Riders were well-known. Teddy Roosevelt was the Secretary of the Navy, and he chose to leave and join Robert Mueller, Baker Mayfield, Rafael Nadal, Michael Phelps, Malcolm Gladwell, and Sebastian Junger.
The men were not nearly as prepared as they should have been. Most of the horses died before they got to Cuba because the Navy had no way to get them there safely.
Roosevelt and his men had to fight their way through the jungle to get anywhere, making any horses they could find useless. They also did not have many weapons.
The men had one black powder cannon, some gatling guns, and black powder rifles. Somehow they were also outfitted in wool uniforms in July in Cuba.
The Spanish had better weaponry, Maxim machine guns, and Mauser rifles. Unfortunately, Arsenio Linares, the Spanish commander, made a few errors that contributed to the Rough Riders' success.
Linares placed all of his gunners at the top of the hill. While their position there was strong, he could not see what was happening at the base of the hill. The Rough Riders were getting hit by sniper fire for hours before Roosevelt asked if they would move forward.
However, the Army denied his request. But, that did not stop Roosevelt and his men from coming up through the 3rd Cavalry and assaulting San Juan Heights.
African-American Soldiers from the 10th Cavalry joined him. Lieutenant John J. Pershing led the Buffalo Soldiers, and one of his soldiers placed the American flag on top of the hill.
Since Roosevelt charged up, Kettle Hill was unprotected. Thankfully, American forces had Gatling guns in place and stopped the Spanish advances.