On 1 July 1898, during the Spanish American War, Lt. Col. Theodore Roosevelt led a charge up what was called San Juan Hill.
When war with Spain broke out in April of that year, Roosevelt was Assistant Secretary of the Navy. He immediately resigned and helped form a regiment of volunteers. The “Rough Riders” enlisted cowboys and college men under the command of Col. Leonard Wood with Roosevelt as his second in command. They arrived in Cuba in time to take part in the Battle of San Juan Hill.
In the confusion surrounding their departure from Tampa, half of the Rough Riders’ troopers were left behind along with all their horses. The volunteers made the charge up San Juan Hill on foot. They were joined in the attack by the 10th (Negro) Cavalry. The 10th never received the glory for the charge that the Rough Riders did, but one of their commanders – Captain “Black Jack” Pershing – was awarded the Silver Star.
There were no glittering bayonets; they were not massed in regular array. There were a few men in advance, bunched together, and creeping up a steep, sunny hill, the top of which roared and flashed with flame. The men held their guns pressed across their chests and stepped heavily as they climbed. Behind these first few, spreading out like a fan, were single lines of men, slipping and scrambling in the smooth grass, moving forward with difficulty, as though they were wading waist high through water, moving slowly, carefully, with strenuous effort. They walked to greet death at every step, and many died, but the others’ waded on, stubbornly, forming a thin blue line that kept creeping higher and higher up the hill. Spanish fire continued, but the blue line crept steadily up, and then, near the top, they gathered and took the heights.
The men of the Ninth and the Rough Riders drove the yellow silk flags of the cavalry and the Stars and Stripes of their country into the soft earth of the trenches, and then sank down and looked back at the road they had climbed and swung their hats in the air.
Roosevelt’s actions during the battle earned a recommendation for the Congressional Medal of Honor but politics intervened and the request was denied.