Cape Cod Cowboy: General Leonard Wood

Cape Cod Life  /  Annual Life 2020 /

Writer: Chris White

Pocasset was the influential childhood home of one of America’s most accomplished figures who was present at some of the country’s most memorable moments.

General Leonard Wood

The cowboy is one of America’s great mythological figures. One of the first motion picture hits, 1903’s “The Great Train Robbery,” was a Western, and the global pop culture phenomenon of 2019—Baby Yoda!—appeared in the Neo-Western television series, “The Mandalorian.” From John Wayne to Clint Eastwood and now to the armored Pedro Pascal, or “Mando,” cowboys have captured the hearts and imaginations of Americans for over 100 years. Their codes of honor, courage, rugged independence, and determination to do the right thing no matter the odds tap into a particular vein of the American Dream. These legends often have little to do with reality, and most of the stories conveniently omit ugly details, but they do capture a certain entrepreneurial spirit of self-sufficiency and strength. The heroes possess “true grit,” and they “speak softly and carry a big stick.” Indeed, few real-life characters did more to create and advance the cowboy legend than Theodore Roosevelt and the Rough Riders; much of the visual iconicism of cowboys derives from this band of soldiers thanks to their unofficial portraitist, Frederic Remington. It’s no coincidence that Remington was a good friend of Roosevelt, and it’s no exaggeration to suggest that the images and lore of the Rough Riders led to the rise of one of America’s best beloved presidents. What’s less universally known is the fact that another friend of Roosevelt’s was the initial organizer and leader of this famed regiment, a man who grew up in a place most unlikely for cowboys—the village of Pocasset in the town of Bourne.

Few would have predicted that Leonard Wood, the son of a Civil War-era doctor, would rise to the top ranks of the U.S. Army from his childhood battlefields of Bourne’s village of Pocasset, where, according to biographer Jack McCallum, “He had few friends, a quick temper, and a reputation for getting into—and winning—fights.” And yet, a series of events and friendships led Wood to the White House, and very nearly to becoming the POTUS in 1920. He was lucky to attend Harvard, one of only two schools in the country at the time where medicine was, as McCallum put it, “going from being a cult to being a science.” After failing in private practice, he signed up as a contract surgeon in the army. The timing coincided with Geronimo’s escape from a reservation in Arizona, and Wood participated in the hunt for the fugitive Apache leader through the mountains of northern Mexico, which represented one of the key moments in “the closing of the American frontier.” He later earned a Congressional Medal of Honor for his service. 

Wood’s Pocasset home

Following Wood’s Arizona campaign, McCallum says, “he talked his way into” an assignment as a surgeon in Washington DC. There, in 1890, he married Louise Adriana Condit Smith, whose legal guardian was  Supreme Court Justice Stephen Field; the entirety of SCOTUS attended the wedding. This led to his development of a bond based upon hunting and card-playing with outgoing President Grover Cleveland. Wood remained in the “executive inner circle” of Washington, in part because the incoming President McKinley’s wife, Ida, was, according to McCallum, “an incorrigible hypochondriac,” and the doctor was “perfectly willing to sit at her bedside, hold her hand, and commiserate with her over illnesses that she didn’t have.” At the time, Wood’s rank was still only that of captain in the medical corps, so the access that he had gained to the president was truly remarkable. It also led to Wood befriending the young Assistant Secretary of the Navy, Theodore Roosevelt. Roosevelt wrote to his wife back in Oyster Bay, NY, “I met a most interesting Doctor Wood from the United States Army who just went through all of that Apache campaign.” They became inseparable friends and remained close for the rest of their lives. McCallum states, “They were young men in a fairly stodgy Washington, and they were not stodgy men.” 

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. 

Wood’s mission was not to rule Cuba indefinitely, but rather to create an independent nation. He managed to co opt the some 40,000 Cuban insurrectionist forces, convert them into police, and McCallum states, “between 1899 and 1900, the American soldiers never fired a shot.” The U.S. Army turned its attention to building roads, bridges, and stringing telegraph lines across Cuba. General Leonard Wood committed 20% of the country’s budget to education, and he oversaw the construction of 3,600 schools. By the time Wood left Cuba in 1903, nearly 200,000 children were enrolled in schools. He also cleaned up the courts and the justice system and expanded access to health care by providing 5,500 hospital beds. “He emptied the orphanages,” says McCallum. “He created a system for adoptions and foster care; he created a social structure on that island, and it was really quite a remarkable performance that took place over three years.” 

Unfortunately, nation building is complex, and soon Cuba would return to strife and oppression rather than develop into a healthy, thriving democracy. A number of factors contributed to this, but McCallum believes that responsibility falls on Wood for one reason in particular—the general had felt strongly that only educated landowners should have the right to vote. McCallum states that when the general left the island, “Fewer than 10% of the Cubans were voting. It was a very narrow base, and it was a base that very quickly crumbled and fell.” Another factor that doomed the young country resulted from the Platt Amendment which contained seven conditions for Cuba after America’s withdrawal, including economic restrictions and the U.S. prerogative to intervene whenever it felt the need. Although he supported the amendment, Wood noted that “We’ve left them free, but we haven’t left them any sovereignty.” Unsurprisingly, McCallum concludes, “The Cubans intensely resented that….That, maybe as much as anything else, poisoned American relations with Cuba for the balance of the 20th century.”

Although General Leonard Wood never again took residence in Pocasset, he did continue to visit. However, the army took him to another island, Mindanao, in the Philippines, where future generals Pershing and MacArthur served under his command. He returned to the U.S. and became the Commanding General of the U.S. Army, and it’s likely that he would have won the presidential election in 1920—“Wood had by far the inside track for that nomination,” states McCallum—but for some last-minute politicking at the Republican Convention that resulted in Warren Harding receiving the nod. With just a few twists of fate, General Leonard Wood of Cape Cod may have left a mark on U.S. history as indelible as that of his cowboy friend, Roosevelt, but as political winds shifted, he finished his career in the Philippines, eventually dying in Boston during surgery to remove a brain tumor. Of the political figures at the turn of the 20th century, McCallum concludes, “There are a scattering of people who were household names during their own lives and got lost in what’s called the dustbin of history, and General Leonard Wood is probably the most characteristic of those.” Wood’s forty-year active service life covered the entire era from the end of Reconstruction through WWI, and “he touched a tremendous number of the parts of that transition.”

For more Cape & Islands’ history, check out our other history stories!

For more on General Leonard Wood, check out Jack McCallum’s book here!

Chris White

Chris White is a frequent writer for Cape Cod Life Publications and has written on topics ranging from the history of Smith’s Tavern on Wellfleet Island to the sinking of the SS Andrea Doria off Nantucket. Chris also teaches English at Tabor Academy in Marion.