Skip to content

Cape Cod Cowboy: General Leonard Wood

Meanwhile, media titans William Randolph Hearst and Joseph Pulitzer were actively drumming up support through their newspapers for a war with Spain, and their influence created tremendous pressure upon President McKinley. Roosevelt and Wood were both eager to advance this cause, so much so that Wood walked into McKinley’s office one day and the president said, “Well, have you and Theodore declared war yet?” Wood’s response was, “No, Mr. President, we have not, but I’m quite confident that you will.” The dominoes began to fall, the USS Maine exploded in Havana Harbor, the U.S. declared war, and Elmer Hawley, the territorial governor of Arizona, an old friend of McKinley’s, wrote that he had a great plan for attack—cowboys. The idea was to form a regiment of volunteers, many of whom had fought against the Apaches, who were used to the heat and to living out-of-doors, and who might even speak Spanish. They could also ride horses and shoot; Hawley reckoned that these cowboys would make the perfect soldiers for conflict in Cuba, and both Wood and Roosevelt heartily agreed. When the First Volunteer Cavalry, later famously and affectionately known as “The Rough Riders,” formed, Roosevelt was given the rank of Lieutenant Colonel, while Wood was promoted to Colonel and served as the unit’s commander. The two friends both recruited volunteers, but in markedly different ways, which led to an eclectic corps of warriors. Wood’s recruitment letter to the “cowboy” element produced a prodigious number of responses; he had to be selective and turn people away. Roosevelt, on the other hand, targeted Ivy League adventurers and asked the National Foxhunters Association to provide 100 good riders. McCallum notes that “He solicited football players from Harvard, baseball players from Yale, and rowers from Princeton, claiming that they all had the physique that would make them perfect soldiers.” At a camp set on fairgrounds in San Antonio, Colonel Leonard Wood took his collection of ranch hands, bartenders, cowboys, and scions of the East Coast elite and trained them up in about six weeks. 

After landing on the southern shore of Cuba, between Santiago and Guantanamo Bay, the Rough Riders fought and won the Battle of Las Guasimas, which led to Roosevelt’s promotion to Colonel. He then assumed leadership of the regiment while Leonard Wood received a promotion to general, and commander of the entire cavalry. Following their victory at the Battle of Kettle Hill, which would later be mythologized as the Battle of San Juan Hill, a number of circumstances aligned which led to General Wood earning the position of Governor of Santiago. Although the Rough Riders took much of the credit for the victory in Cuba, in large part because the image of this ragtag band of cowboys was so endearing to the audience back home, the U.S. Navy had actually done the lion’s share of the lifting in the war. 

While it may seem relatively commonplace in 2020 for U.S. forces to take control of an area on foreign soil, back in 1898 the country had very little experience of this sort. The army had worked as an expansionist force throughout the West, but Cuba was something new and different. Because Wood did such a good job of managing Santiago—and its challenges of poverty, sanitation, starvation, disease, and insurrection—the army promoted him again, this time to serve as Military Governor of the eastern end of the island. According to McCallum, he had proven to be “a natural administrator and a zealous autocrat. He combined his medical training with his force of personality to mobilize the city’s population and turned an infamous cesspit into a livable city.” Wood soon became Governor General of all of Cuba. Thus, in just two years, he had risen meteorically from a lowly captain in the medical corps to the leader of an entire country. Of course, while Wood ran Cuba, his Rough Rider comrade rose first to serve as Vice President, and following the assassination of McKinley in 1901, to POTUS. 

You might also like:

Latest Editions

The Latest Edition of Cape Cod HOME Magazine The Latest Edition of Cape Cod ART Magazine

  • Stay Connected

    Sign up for our newsletter
  • This field is for validation purposes and should be left unchanged.