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The Boys of '98: Theodore Roosevelt and the Rough Riders

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Spur Awardwinning author Dale Walker tells the colourful story of Americas most memorable fighting force, the volunteer cavalry known as the Rough Riders. From its members, and their slapdash training in Texas and Florida, to its battles at Las Gusimas and San Juan Hill under the command of Theodore Roosevelt, who kept riding, some say, into the White House.

304 pages, Paperback

First published January 1, 1998

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Dale L. Walker

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Displaying 1 - 7 of 7 reviews
Profile Image for Luke Mohamed.
109 reviews
June 12, 2022
Gained a bit of insight beyond Roosevelt's coverage in his autobiography.
Profile Image for Andrew Canfield.
545 reviews4 followers
March 14, 2019
The Boys of ‘98 is singularly focused on the Spanish-American War and the the service of the First U.S. Volunteer Cavalry within the context of this conflict. It marks the second Rough Rider-related book read during research on a Theodore Roosevelt-related project.

The book opens with a brief but effective history of the late nineteenth century situation in Cuba, providing readers with the context in which the Spanish-American War took place. Instead of beginning with guns blazing in Manila Bay or on the shores of Cuba, The Boys of ‘98 makes a point not to ignore the reasons and nuances behind the broader war.

The recontrentrado policy that caused so much death and controversy, as well as the Cuba Libre movement and Yellow Journalism in the United States, are covered in the process of laying the groundwork behind why the Spanish-American War started.

The Boys of ‘98 also provides curt biographical sections on men who helped shape public perceptions of the day; the likes of Richard Harding Davis, Stephen Crane, and Frederic Remington receive (cursory) focus, but enough to recount the role they played not only on domestic matters like the changing culture and rise of the American far west as a major factor, but in making or breaking public support for U.S. interventions in places like Cuba. Intertwined with this brief Spanish/Cuba history is an equally succinct summation of Theodore Roosevelt’s rise up the ladder in New York City, state, and eventually Washington, D.C.

All of this leads up to the sinking of the U.S.S. Maine, and the fallout from this event is much better understood after the ground covered by Dale L. Walker. Following the horrific sinking, there is the recounting one might expect in a story about the Rough Rider unit. Theodore Roosevelt’s resigns from the military bureaucracy to help raise a unit of Western territory volunteers. These volunteers would then go on to train in San Antonio, where Roosevelt’s friendship with Colonel Leonard Wood (the man he recommended that Secretary of War Alger appoint as first in command of the Rough Riders) further blossomed during their brief late spring 1898 training stint on San Antonio’s fairgrounds.

The cast of diverse characters, comprising desperadoes from the West and Indian Territories as well as well-heeled New Yorkers, are given the same sort of cursory descriptive treatment that was provided Remington and the Cuban-bound journalists. Readers nevertheless get a good feel of the First Cavalry Unit's composition.

Wood, Roosevelt, and their men are shipped off to Cuba via Tampa in order to assist the rebels' effort to kick the Spanish off their island. The book shows how the Cuban rebels, allegedly held in such high romantic esteem by those who pushed for intervention in the first place, were all but shunted off to the side during and after the American military’s arrival.

In keeping with his unwillingness to overlook the opinion makers of the day, Walker gives an unflinching analysis of just how much benefit Lieutenant Colonel Theodore Roosevelt received from the favorable coverage provided by the journalists who traveled to Cuba alongside the military. Richard Hard Davis’s relationship with the 1st Cavalry was described as “almost symbiotic.” As a veteran of the Santiago campaign wrote, “The Rough Riders were the supreme of the elite; no regiment has ever received the newspaper space that was devoted to them...In addition to having Teddy as its second in command, this regiment had its own press agent in Richard Harding Davis, to whom the human beings not listed in the Social Register were merely varied forms of pollution.”

The Boys of ‘98 then recounts the standard fare: the sloppy loading in Tampa and unloading on the shores of Cuba of the American military; the somewhat derided performance by the Rough Riders at Las Guasimas; the fearlessness shown by many, Roosevelt included, during the taking of San Juan Hill.

Walker’s writing gives readers a good grasp of the Spanish and American perspectives and the circumstances behind each sides' strategies leading up to the San Juan Hill charge. His assessment is that the U.S. nearly squandered the tremendous advantages they had against the Spanish in Cuba, quoting Leonard Wood’s statement that the U.S. was lucky to be sparring “with a broken-down power, for we would surely have had a deuced time with any other.”

Small disagreements between U.S. Navy Admiral William Sampson and Army leader General Rufus Shafter are documented as well, going to show that the book makes an effort to provide a fair judgment of the war's prosecution. Although Calixto Garcia does play a small role in The Boys of ‘98, it would have added more depth if Cuban rebel leaders like himself had more paragraphs devoted to fleshing out their motivations and heroics.

Army General Shafter comes off looking like a below average wartime general, nearly squandering successes the Rough Riders had aided in by pulling off an unnecessary withdrawal. This seemingly is stopped because he is overruled by generals Joe Wheeler and Jacob Kent on the spot. The ultimate U.S. victory almost seems like it was accomplished in spite of the decisions made by the higher-ups in the regular military. Roosevelt’s bravery, which to the future president's chagrin never earned him a Medal of Honor during his lifetime, is even overshadowed at time by criticism of his usage of the Rough Riders in what some saw as not the most tactical of manners.

A debate over whether or not the term “ambush” classified what the Spanish did to Roosevelt’s men at Las Guasimas underscored the potential for shading the news to benefit or undermine the U.S. public's response to the Cuban intervention. The perception of those back home of what was going on on the island off the Florida coast was shaped by the words in journalists’ dispatches back to their papers and magazines.

The book closes with the return of those who survived back to the United States, a return which itself was not uncloaked in controversy. Concern swelled in the War Department that Roosevelt was showing them up by writing a letter asking for his men to come home. The reasoning for departure from Cuba soon after victory was due to concern with the tropical diseases rampant during the island's hot season. This caused a brief flare up between the Rough Rider leader and the Army brass in D.C.

The esteem Roosevelt’s men held him in was shown by the presentation to him of a Bronco Buster statue crafted by Frederic Remington after his unit's arrival back on American shores in New York.

The Boys of ‘98 is an overall solid history of the Cuban theater of the Spanish-American War. It gets the job it set out to do accomplished, filling readers in on the circumstances and scenarios surrounding the sending of troops to Cuba. What they did to assist Generals Demetrio Castillo and Calixto Garcia's efforts to bolster the Cuban Libre movement are recorded in efficient prose. This will stand up as one of the better works recounting several important months in the history of the United States and Cuba.

-Andrew Canfield Denver, Colorado
339 reviews10 followers
August 3, 2016
This book is a great example of history as entertainment. Despite a tendency to repeat facts, it is well written and researched. If you have an interest in the Spanish American War, the Rough Riders, or Teddy Roosevelt, you can't go wrong with this book as an introduction to these topics.

In some ways, it was a silly little war, poorly lead and executed on both sides. The fame of the Rough Riders far surpassed the fact that the regiment existed for only around six months. The US won the war despite the fact that the commanding general in Cuba was a 300 pound man too obese and gout ridden to sit a horse and the commander of the US Calvary was a Confederate veteran who occasionally thought he was back fighting the Yankees.

More importantly, this little war had monumental effects. It was a conflict between a dying empire and a rising power. The aftermath of the war left the US a global colonial power, with all the good and bad that entails.

This book brings the people involved in these events to life and is well worth spending time with.
Profile Image for Tatoosh.
5 reviews
August 3, 2011
A very informative work that concentrates on the Rough Riders but sheds worthwhile light on the people involved from Teddy R to Leonard Wood, who went on to fame in the Philippines. For its size, it does an impressive job of recreating the time and diverse elements that went into forming the Rough Riders, plus it gives a fairly unvarnished view of their campaign in Cuba.

For Spanish American War buffs or even Philippine American War students who want more insight into the times and people, this is a very good read.
Profile Image for Catherine.
1,067 reviews17 followers
March 3, 2012
Not the book’s fault; I’m sure military buffs would love it. It’s pretty much just military training and battle recaps and analysis, while I was hoping for a serving of Cuban history and culture along with Teddy Roosevelt.
31 reviews
August 4, 2011
Teddy Roosevelt is such an interesting character in US history - this is a really good book!
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