In 1898, Cuba gained independence from Spain after four centuries of colonial rule. However, this did not bring full autonomy. As the United States stepped in to end Spanish occupation, the foundations of Cuba–U.S. relations were laid under a Washington-appointed military government. Rather than allowing Cuba to govern itself immediately, the United States installed a temporary administration that ruled the island for four years, eventually bringing Leonard Wood in Cuba to lead a transformative military government.
Although these four years significantly shaped Cuba’s development, researchers still devote little attention to analyzing this period.
General Brooke and the Start of U.S. Military Rule
General Robert Brooke, a veteran of the American Civil War, was the first military governor of Cuba, although his tenure was brief. During his time in office, one of his top priorities was expanding education. At the time, Cuba had only about 300 public schools, and literacy rates were extremely low. However, Brooke drew criticism when he proposed banning gambling, a measure that included shutting down clubs and dance halls. These restrictions threatened entertainment venues that generated tourism and revenue from abroad.
With limited political experience and no clear guidance from Washington or President McKinley, Brooke often appeared unprepared to govern Cuba. For example, he suggested banning machetes to promote public safety. Yet this proposal failed to consider its negative impact on harvesting sugar cane, Cuba’s most important resource.
Leonard Wood in Cuba: Early Foundations of Cuba–U.S. Relations
General Leonard Wood was among Brooke’s most outspoken critics. Wood had already gained military prominence for leading the Rough Riders during the Spanish-American War. Under his command, this volunteer cavalry regiment achieved key victories, including the pivotal charge up San Juan Hill. His close friendship with Theodore Roosevelt, who admired Wood’s leadership and military judgment, also proved advantageous. Roosevelt’s growing national influence strengthened Wood’s position further.
As dissatisfaction with Brooke’s leadership increased, Roosevelt used his connections to advocate for a change. He personally urged Secretary of War Elihu Root to appoint Wood as Brooke’s replacement. This recommendation carried substantial weight. By December 1899, Wood officially assumed the role of military governor.
Wood approached his new position with marked energy and ambition. He quickly implemented reforms to rebuild the war-torn country, strengthen public health, and address the needs of the Cuban population. His leadership style and commitment to structural improvements significantly shaped Cuba–U.S. relations and the broader post-war landscape. His tenure stood in sharp contrast to that of his predecessor.
Education Reform Under Leonard Wood’s Administration
During the period of Leonard Wood in Cuba, education reform became one of the administration’s most ambitious goals. The Wood administration enacted sweeping reforms across the island. One of the most significant achievements was the expansion of the public school system, continuing one of Brooke’s earlier priorities. By the time the United States withdrew from Cuba, Wood had increased the number of public schools by nearly 3,000 and dedicated about a quarter of the national budget to education. Attendance also became mandatory for children between the ages of 6 and 14. Although individual schools retained control over their curricula, the administration created a school board that required teachers to submit monthly and annual reports. Failure to comply could result in delayed salaries. These measures aimed to create a more stable and professional educational system.
Legal and Infrastructure Reforms
Another major accomplishment of Wood’s administration was the attempt to reform the legal system. He authorized the construction of several new courthouses and removed officials he viewed as corrupt or incompetent. He sought qualified replacements, but progress remained limited. Because the jury system was not part of Cuba’s legal tradition, it lacked an institutional foundation to function effectively. Judges often dismissed cases without decisions, and the police force was understaffed and poorly trained. As a result, officers lacked the skills needed to enforce rulings or protect themselves from threats of violence.
Cuba’s infrastructure faced even greater challenges. After multiple wars for independence, the island was left with very few roads or railways connecting rural areas to cities. This deterioration worsened during General Weyler’s Reconcentration policy, an episode we examine in detail in our article on Cuba’s concentration camps. Sewer systems were clogged and deteriorating. Homes were overcrowded, and access to clean water was scarce. Death rates in Havana were two to three times higher than in similar cities, largely due to diseases linked to unsanitary living conditions.
During Wood’s tenure in Cuba, the administration invested substantial resources in street cleaning, sanitation, road construction, and the expansion of railways. It also funded park restoration and other public improvements. In just four years, the military government achieved remarkable progress in rebuilding the nation. These advances in public health and infrastructure left a lasting impact on Cuba–U.S. relations, even as tensions grew over political control.
Elections, Suffrage Limits, and Rising Tensions
Because the United States did not intend to remain in Cuba indefinitely, the Wood administration established election rules intended to preserve the political path it had created. Concerned that radical factions might gain power after U.S. withdrawal, Wood supported limited suffrage that excluded illiterate citizens. He also argued that universal suffrage would discourage foreign investment. Therefore, upcoming elections would be restricted to literate men over age 21 who owned property valued at $250 or more or who had served in the Cuban army during the war against Spain. These requirements excluded roughly two-thirds of the population.
Despite these limits and Wood’s efforts to campaign on behalf of the Union-Democratic Party, the results did not favor him. Most elected officials were individuals he believed would not support U.S. interests or promote Cuban economic growth.
Although the Wood administration raised standards of living in many areas, the Cuban desire for self-governance remained stronger. This sentiment persisted for decades, as later Cuban leaders shaped their policies to fit U.S. economic interests. Eventually, the revolution led by Fidel Castro and the establishment of a one-party state emerged from a long history of resentment toward U.S. political influence. Despite the shortcomings of Castro’s government, many Cubans supported it because it symbolized independence.
Why Cuba–U.S. Relations Still Matter Today
Whether one believes that the United States acted out of self-interest or genuine goodwill, policymakers during the military government viewed Cuba’s economic development as beneficial to the United States. A sustained model of growth would have helped both nations. If the United States had adopted a more cooperative approach rather than relying on coercion, many of the tensions that followed might have been avoided.
More than a century later, Cuba–U.S. relations remain strained by a Cold War–era embargo and by various forms of U.S. intervention that continue to shape daily life on the island. Today, rebuilding ties requires a different strategy. A relationship based on cooperation rather than pressure would honor Cuba’s sovereignty while opening opportunities for economic growth, regional stability, and cultural exchange.
The decisions made during the period of Leonard Wood in Cuba helped define the long-term dynamics between both nations throughout much of the twentieth century.
For the United States, renewed engagement could repair a fractured history and create openings for trade, diplomacy, and security partnerships. For Cubans, it could offer greater economic possibilities and a stronger sense of dignity, as many still endure the burdens of persistent poverty. Ultimately, a more constructive relationship serves the interests of both countries and the hemisphere as a whole.
References
Hitchman, J. H. (1968). The American Touch in Imperial Administration: Leonard Wood in Cuba, 1898-1902. The Americas, 24(4), 394–403. https://doi.org/10.2307/980225
Lane, J. C. (1972). Instrument for Empire: The American Military Government in Cuba, 1899-1902. Science & Society, 36(3), 314–330. http://www.jstor.org/stable/40401653
Lamrani, S. (2021). The origins of the Cuban Revolution of 1959. Études Caribéennes, (50). https://doi.org/10.4000/etudescaribeennes.24239
Pérez Jr, L. A. (1985). Insurrection, Intervention, and the Transformation of Land Tenure Systems in Cuba, 1895–1902. Hispanic American Historical Review, 65(2), 229-254. Retrieved from https://read.dukeupress.edu/hahr/article/65/2/229/148269/Insurrection-Intervention-and-the-Transformation