The last of Teddy Roosevelt’s ‘Rough Riders’ died in 1987

The people who live through the world’s most historic events are the best connection to our past. Today, as we lament the growing losses of veterans who fought in World War II and the Korean War, it can still be a surprise that we are so close in time to the wars of the 19th Century. Just 34 years ago, we lost our only connection to the “Rough Riders,” the volunteer cavalry regiment that famously stormed San Juan Hill with Col. Theodore Roosevelt.

Ralph Waldo Taylor, who enlisted at age 16, wasn’t the last veteran of the Spanish American War, but he was an important connection to its memory. 

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The Spanish-American War broke out in 1898 after the USS Maine exploded in Havana Harbor, which was then occupied by Spain. Tensions had been mounting between the United States and Spain for decades between the two countries, inflamed by the “muckraker” journalism popular at the time.

Sensational stories, not all of them exactly true, filled newspapers as each competed for bigger and bigger circulation. Finally the powder keg blew (literally) when the Maine was destroyed. The newspapers claimed the ship struck a Spanish mine in the harbor and President McKinley was pressured to ask Congress for a declaration of war. 

Among the most excited to see action was Theodore Roosevelt, who resigned from his position as Assistant Secretary of the Navy to help raise a regiment of volunteers. The unit he formed was the 1st U.S. Volunteer Cavalry. Originally under Col. Leonard Wood, Roosevelt soon found himself in command. 

The Rough Riders, as they were called after Roosevelt assumed command, was made up of  Western frontiersmen, Ivy League athletes and Native American tribesmen, among others. One of its volunteers was a young, 16-year-old named Ralph Waldo Taylor.

The young man deployed with the Rough Riders to Cuba in 1898 and though it was supposed to be a cavalry unit, its horses were not deployed with them. The 1st U.S. Volunteer Cavalry was in reality fighting like an infantry unit. 

Teenage Taylor was with Roosevelt and the Rough Riders when they marched to the base of San Juan Hill, a heavily-defended high ground that seemed impregnable from their vantage point. They took cover at the base of nearby Kettle Hill to avoid sniper and artillery fire, but quickly found themselves pinned down. 

After the attack began, the unit's orders forced them to hold their position, even under heavy enemy fire. Roosevelt grew frustrated with the situation and, disregarding orders, led a charge up San Juan Hill. Within 20 minutes the hill belonged to the Americans. 

Taylor lied about his age to enlist in the New York National Guard. He eventually told his wife, Bessie, about what happened that day.

“They charged up the hill in waves, trying to knock out the Spaniards in a blockhouse at the top,” she told UPI in 1987. “Ralph was in the second or third wave and he used to tell how some members of his company were killed as they ran up the hill beside him.”

For Roosevelt, the victory meant election to the governor’s mansion in New York and eventually being named Vice-President of the United States. When McKinley was assassinated in 1901, he assumed the office of President. For Taylor, life carried on the way it does for many war veterans: he took a job. 

In 1986, Taylor was informed by the U.S. government that he was one of a few surviving combat veterans of the era, and that he was the only survivor of San Juan Hill still living. 

“He could visualize all the thousands who fought with him and it overwhelmed him that he was the only one left,” she said.