Teddy and his Rough Riders: Yes they did take San Juan Hill



Readers, Mark Lee Gardner has written a fascinating book about Teddy Roosevelt and his Rough Riders, names everyone knows, but no one knows much about.

Here’s the first interesting fact. Although some writers have claimed Teddy did not storm San Juan Hill, or Heights, in fact he and his men did that very thing.

With the declaration of war with Spain in April 1898, Theodore Roosevelt conceived the idea of raising a cavalry regiment recruited from Western businessmen, cowboys and outdoorsmen.

Roosevelt then inspired men to join the 1st U.S. Volunteer Cavalry, better known as the “Rough Riders.”

 Rough_RiderRoosevelt, a former New York National Guardsman, helped to organize the regiment and was appointed its lieutenant colonel.

After training in Texas and Florida, the Rough Riders landed in Cuba, without their horses. 

It was during the Battle of San Juan Hill, on July 1, 1898, that the Rough Riders, under Roosevelt, made their mark in American military history.

Teddy and some of his Rough Riders
Teddy and some of his Rough Riders

Ordered to seize Kettle Hill in support of the main attack, the Rough Riders fought their way to the top despite heavy enemy fire.

After taking the hill, the Rough Riders continued their attack, seizing San Juan Heights, which overlooked the city of Santiago.

The American victory led to the Spanish surrender two weeks later.

Here’s the interview.

ROBB: The thing that first impressed me about the Rough Riders was their innocence, their naivety, their eagerness to fight in a war in which they could be killed. It seems the national nightmare, the Civil War, would have made them somewhat wary. Did you get the same impression while researching?

GARDNER: The young men who enlisted in the Rough Riders were definitely naïve. They had grown up with the West_minstrel_jubilee_rough_ridersstories of the great Civil War (several were sons of Civil War veterans), and they longed for their own war and their own chance to win laurels on a battlefield. But as one Rough Rider wrote later, “To those who never soldiered in war times there is a halo that is inviting, but to those who have, there is no halo. It only comes with the years afterward when all things are softened as into a dream.”

ROBB: I compare the Rough Riders to soldiers today and they do not seem to be the same kind of people. Roosevelt’s men were like men playing on a college football team while the soldiers today are seemingly aware of the horrors of war; they seem more sophisticated.

GARDNER: Television, beginning with the coverage of the Vietnam War, and, in more recent years, the Internet, have made us aware, and in the most graphic ways possible, of the true horrors of combat. So, yes, it’s not surprising that the soldiers of today are savvier about what they are getting into than the volunteers of 118 years ago. However, the fighting in Cuba was no sporting event, and the Rough Riders were as brave and steady as any soldiers on a battlefield before or after.

 ROBB: I got the same impression about American culture in the Spanish-American War era; it was cohesive, innocent and shallow. For instance, nobody seemed to ask why Cuba was our war. That’s not how it is today.

GARDNER: I didn’t delve deeply into the politics of the Spanish-American War in my book simply because there are plenty of volumes out there that treat that subject. My aim was to tell the story of this legendary volunteer regiment and its charismatic leader through the eyes of the participants.

There were many in the United States who questioned the war, but there were many more who supported it. The cause of Cuba Libre found much sympathy with Americans, who easily recalled the history of their own struggle for independence. It was the sinking of the USS Maine in February of 1898, however, that most shaped popular support for war against Spain.

ROBB: Who sank the Maine? Did the Spaniards sink the ship or ????? uss-maine-explosion-large

GARDNER: The exact cause of the explosion of the Maine is still debated. I think most historians believe the powder magazine of the ship ignited accidentally.

However, the U.S. Navy assembled a board of inquiry to determine the cause, and it concluded that the Maine “was destroyed by the explosion of a submarine mine.” The vast majority of Americans accepted this report and pointed their fingers at Spain as the perpetrator.

ROBB: Did you find it ironic that the Rough Riders seemed to disdain the Cuban rebels, yet were in Cuba to ostensibly help them defeat the Spanish?

mambi6GARDNER: Most Rough Riders, including Roosevelt, were disappointed in what they saw of the Cuban insurrectos. Their clothing was in tatters, and their arms varied greatly in quality. It didn’t help that the Cubans failed to come through with the promised support in the subsequent fighting.

At least one Rough Rider, though, recognized what the Cubans had been up against, writing that “after all, they kept three hundred thousand Spaniards guessing for three years – no slight achievement.”  14e10fe90c45fd612f68c0e4d5e7b889

ROBB: The 10th cavalry (African-Americans) seemed to fight well, yet I never heard anything about their assistance in fighting the Spanish.

GARDNER: There were four regiments of Buffalo Soldiers, two of cavalry and two of infantry, in Cuba, and each of those regiments displayed real fighting spirit during the campaign.

The Spaniards called these black soldiers Yankees ahumados: smoked Yankees. They may not have gotten much press in the States, but they certainly impressed the Rough Riders who fought alongside them. “I tell you,” wrote one Rough Rider in a letter home, “the black boys set a pace that is damn hard to keep up with, for they fight like demons and never know when to stop.”

ROBB: I got the impression that Roosevelt and other officers just marched into fights and there was little planning or tactics, or strategy, involved. Is that true?

GARDNER: There was little strategic planning or direction. The commanding American general in Cuba, William Shafter, weighed more than three hundred pounds and suffered from gout. shafter-horseback

(Shafter) was sick in his tent for the Battle of San Juan Heights of July 1, 1898, and communications between his headquarters and the battlefield took far too long, forcing subordinates to issue orders on their own initiative. As Roosevelt wrote later, the battle was “essentially a troop commanders’, indeed, almost a squad leaders’, fight.”

ROBB: Did having so many upper crust soldiers, Harvard men, etc. make a difference in what happened in Cuba?

40532997_1_lGARDNER: The millionaires and Ivy Leaguers, for the most part, pulled their own weight in the regiment. The only real difference came from some of these men and their families donating money and supplies for the entire outfit.

Woodbury Kane, a wealthy New Yorker, had his sister send to Cuba six hundred tins of premium Golden Sceptre tobacco and several cases of canned peaches for the troopers. He instantly became, as one Rough Rider wrote, “the most popular man in camp.”

ROBB: Teddy Roosevelt was an unusual person, wasn’t he? It seems hard to compare him to anyone else in American history.

GARDNER: No American, living or dead, can compare to Theodore Roosevelt. He is endlessly fascinating. One Rough Rider commented to his mother that Roosevelt was “the most magnetic man I ever saw.” He inspired his men to no end, and they would literally follow him anywhere.

ROBB: Would Teddy have been elected president if he hadn’t organized and ridden up San Juan Hill with the Rough Riders? Charge_of_the_Rough_Riders_at_San_Juan_Hill

GARDNER: Well, TR ran up San Juan Hill, his horse, Little Texas, having been left behind at a barbed wire fence.

But to answer your question, he may still have become president, but I don’t think it would have happened nearly as quickly. His heroics in Cuba (he was nominated for the Medal of Honor by all his commanding officers) put him in the national spotlight. This led directly to his being elected governor of New York in November, 1898, which was followed two years later with his spot on the Republican ticket in 1900 as vice president under McKinley. Roosevelts-Rough-Riders-At-Camp-Wolf-Rises-in-the-Heart-Quote

ROBB: The Rough Riders also seemed different from other men you’ve written about. For instance, the men who fought in the Lincoln County War, and the James Gang and the lawmen who hunted them. What do you think about that?

GARDNER: There were actually a few wanted men, and even a couple of murderers, in the Rough Riders. But you’re right, most were not anything like the outlaws I have written about in the past. Billy the Kid and Jesse James were charismatic, and they seem to have been natural-born leaders, but Roosevelt was both charismatic and a genius to boot.

I think Jesse and Billy would have been drawn to TR, but not vice versa. 

Frank James actually volunteered to serve as a personal bodyguard to Roosevelt after an assassination attempt on the former president during his Bull Moose campaign of 1912.



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