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Cape Cod Cowboy: General Leonard Wood

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!



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