The charge up an obscure Cuban hill on July, 1 1898 was a pivotal point in Theodore Roosevelt’s political career. When war broke with Spain in April of that year, Roosevelt was serving as Assistant Secretary of the Navy.
He immediately quit his position and helped form a regiment of volunteers. The “Rough Riders” enlisted cowboys and college men led by Roosevelt under the command of Leonard Wood. They arrived in Cuba in time to take part in the Battle of San Juan Hill.
Roosevelt later described the conflict as a “splendid little war” and for him it was. His combat experience consisted of one week’s campaign with one day of hard fighting. “The charge itself was great fun” he declared, and “Oh, but we had a bully fight.” His actions during the battle earned a recommendation for the Congressional Medal of Honor but politics intervened and the request was denied. The rejection crushed Roosevelt.
As though in consolation, the notoriety from the charge up San Juan Hill was instrumental in propelling him to the governorship of New York in 1899. The following year Roosevelt was selected to fill the Vice Presidential spot in President McKinley’s successful run for a second term. With McKinley’s assassination in September 1901, Roosevelt became President.
In the confusion surrounding their departure from Tampa, half the members of the Rough Riders 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 (who later commanded American troops in World War I) - was awarded the Silver Star.
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