Facts About The Battle of San Juan Hill, from Major Blunders to Remarkable Bravery

Photo by Buyenlarge/Getty Images

The Battle of San Juan Hill is most notable for the participation of the Rough Riders. This skirmish made a hero out of the founder of that regiment, future President Teddy Roosevelt. But that was not the only interesting thing about the fight. Below are five facts you might not know about the 1898 battle.

A future legendary leader participated in the Battle of San Juan Hill

Gen. John J. Pershing sits at his desk
Gen. John J. Pershing sits at his desk (Photo Via Getty Images)

When the Spanish American War first broke out, John J. Pershing was an instructor at West Point. He had previously commanded the 10th Calvary, one of the original Buffalo Soldier regiments, made up of African American soldiers.

His relationship with the 10th Calvary made him unpopular with his cadets, who referred to him as Black Jack (and worse). Pershing soon took part in the Battle of San Juan Hill, again commanding the regiment. The 10th Calvary fought remarkably bravely during the fight and one of the members of the regiment, Sgt. George Berry was the first to reach the top of the hill.

Pershing later became a legendary figure in the US Army, leading the American Expeditionary Forces to victory during World War I. He was also a mentor to future generals like George S. Patton, Dwight D. Eisenhower, and Douglas MacArthur. Pershing is the only American to be promoted to General of the Armies in his lifetime. This is the highest honor granted in the United States Army.

Roosevelt almost cost the US the Battle of San Juan Hill

Teddy Roosevelt and his Rough Riders during the Spanish American War
Teddy Roosevelt and his Rough Riders during the Spanish American War (Photo by Smith Collection/Gado/Getty Images)

Theodore Roosevelt grew up frail and sickly. But over time, he mentally and physically developed himself into a powerhouse. And the Spanish-American War provided him with the fight he had been waiting for his entire life. In 1898, he left his post as the Assistant Secretary of the Navy and formed the First US Volunteer Cavalry Regiment along with Army Colonel Leonard Wood.

When he got to the battlefield, Roosevelt was perhaps a little too eager. During the fight, the future President and his Rough Riders charged up San Juan Hill. But when he did so, Kettle Hill was left lightly defended. The Spaniards tried to take advantage and counterattacked. Thanks to the use of Gatling guns the American forces were able to hold them off. Roosevelt later received the Medal of Honor for leading the charge.

The Americans were not prepared to fight in the Cuban environment

The 16th Infantry during the Battle of San Juan Hill
The 16th Infantry during the Battle of San Juan Hill (Photo Via Getty Images)

Cuba presented a unique environment for the American troops and they were woefully unprepared. The first issue was getting the horses to the island. There was no good way to do so and many of the horses drowned. Once they did get to the island, the troops had to cut through dense jungles to get anywhere. There was also an issue with their uniforms. The soldiers had been issued heavy wool uniforms despite the fact that the operation was being conducted in the middle of July.

The American troops were also understocked on weaponry. They came in with only one cannon and a handful of Gatling guns. Their rifles also released black gun powder in the air when fired, which gave away American positions. By comparison, the opposing Spanish forces were equipped with smokeless Mauser rifles.

The Rough Riders were famous even before the Battle of San Juan Hill

Teddy Roosevelt and the Rough Riders stand at the top of San Juan Hill
Teddy Roosevelt and the Rough Riders stand at the top of San Juan Hill (Photo by Buyenlarge/Getty Images)

While the Battle of San Juan Hill is the most notable accomplishment of the Rough Riders, they were pretty well known beforehand. Roosevelt was, of course, the most famous member of the regiment. He came from a prominent family and was serving as the Assistant Secretary of the Navy before the war broke out. Leonard Wood, who co-founded the regiment with Roosevelt had formerly served as the White House physician.

Among the other members of the group were cowboys, ranchers, miners, and other figures of renown. The group even had 3 famous animal mascots. There was a golden eagle who was called Teddy, a dog named Cuba, and a lion dubbed Josephine. Roosevelt said the lion, “was always trying to make a meal of [him], especially when we endeavored to take… photographs together.”

The Spanish made a number of mistakes that helped the US win

Spanish and American Troops do Battle at San Juan Hill
Spanish and American Troops do Battle at San Juan Hill(Photo by Charles Phelps Cushing/ClassicStock/Getty Images)

The Spaniards had some significant advantages going into the battle. They were much more familiar with the hot and jungle-like terrain. They also had the Americans outgunned. While US forces came in with a small stock of cannons and Gatling guns, the Spanish troops were equipped with Maxim machine guns and smokeless Mauser rifles.

The leader of the Spanish forces, Arsenio Linares, failed to fortify his gunners near the bottom of the hill where they would have had clear lines of sight. Instead, the gunners stood at the top of the hill where they had trouble keeping up with the movements of the emerging American troops during the Battle of San Juan.

Todd Neikirk

Todd Neikirk is a New Jersey-based politics, entertainment and history writer. His work has been featured in psfk.com, foxsports.com, politicususa.com and hillreporter.com. He enjoys sports, politics, comic books, and anything that has to do with history.

When he is not sitting in front of a laptop, Todd enjoys soaking up everything the Jersey Shore has to offer with his wife, two sons and American Foxhound, Wally.