What If: The Caribbean Confederation

How a Failed Coup Could Have United the Islands

On March 10, 1952, former Cuban President Fulgencio Batista launched a military coup against the elected government of President Carlos Prío Socarrás. The coup succeeded in hours, establishing a dictatorship that would last until Fidel Castro’s revolution toppled Batista on January 1, 1959. But what if Batista’s coup had failed? What if that failure had catalyzed a movement for Caribbean unity—bringing together Cuba, Haiti, the Dominican Republic, and eventually Puerto Rico into a confederation designed to resist American imperialism and chart an independent path?

This is the story of how one prevented coup could have sparked the creation of the Caribbean Confederation, transforming the region’s twentieth-century history and offering an alternative to both American domination and communist revolution.

The Coup That Almost Failed: March 1952

In our actual history, Batista’s coup succeeded through surprise and swift action. On the night of March 9-10, 1952, Batista and a small group of officers seized Camp Columbia, Havana’s main military base, along with other key installations. President Prío, caught completely unprepared, fled to the Mexican embassy and then into exile. The coup was bloodless, swift, and irreversible.

But coups are fragile operations depending on split-second timing, military loyalty, and the courage or cowardice of key individuals. Imagine a slightly different sequence of events.

In our alternate timeline, Cuban military intelligence receives credible information about suspicious officer meetings at Camp Columbia. Major Ramón Barquín—a reform-minded officer who historically opposed Batista and attempted his own unsuccessful coup in 1956—commands the loyalty of several strategic units. Concerned about the activity and aware of Batista’s ambitions, Barquín alerts President Prío on the evening of March 9.

Rather than dismissing these concerns, Prío takes them seriously. Perhaps recent political instability has made him cautious, or perhaps he’s heard corroborating rumors. He orders loyal military units to secure government buildings and goes on national radio at 10 PM to announce that he has information about a planned coup attempt. Any military action against the constitutional government, he declares, will be considered treason.

This public warning changes everything. When Batista and his co-conspirators move to seize Camp Columbia at midnight, they discover that other military units are on alert. Loyalist forces surround the base. A tense standoff develops. Some of Batista’s supporters, realizing the coup isn’t the swift action they were promised, defect. By dawn on March 10, the coup has clearly failed. Batista lacks sufficient military support and, unwilling to trigger civil war, agrees to surrender in exchange for safe passage into exile.

By March 12, 1952, Batista is in Florida, and President Prío has survived the most serious threat to Cuban democracy since the Constitution of 1940 was adopted. But the near-death experience fundamentally transforms Cuban politics.

The Post-Coup Reckoning: Reimagining Cuban Sovereignty

The failed coup triggers intense national reflection. Political leaders, intellectuals, and ordinary citizens grapple with a crucial question: How did Cuba come so close to losing its democracy, and how can this be prevented in the future?

Several answers emerge. First, many Cubans argue that their nation never truly achieved independence despite the formal end of Spanish rule in 1898 and the abrogation of the Platt Amendment in 1934. The United States still owns much of Cuba’s infrastructure, controls its sugar industry, and maintains Guantánamo naval base. American economic dominance and political influence remain overwhelming.

Critics note that Batista likely believed American support—or at least acquiescence—would be forthcoming. After all, he had worked closely with American military and intelligence officials during World War II. The near-success of his coup proves that Cuban democracy is vulnerable as long as Cuba remains within the American sphere of influence.

Second, the coup reveals that Cuba’s military is dangerously politicized. Too many officers see themselves as political actors rather than servants of the constitutional order. Military reform becomes urgent, but the question is how to ensure loyalty without creating a police state.

Third, Cuba’s sugar-based economy makes it vulnerable to American economic pressure. When sugar prices fall or American quotas change, Cuba’s entire economy trembles. Diversification is necessary, but Cuba alone lacks the market size and resources to build industrial capacity.

Out of these conversations emerges a bold idea: Cuba cannot secure its independence alone. What Cuba needs is a Caribbean confederation—a union of Caribbean nations that can collectively resist American dominance, pool resources for development, and create a democratic alternative to both U.S. imperialism and European colonialism.

Architects of a New Vision: 1953-1954

President Prío, his legitimacy strengthened by defeating the coup, becomes an unlikely champion of Caribbean confederation. He appoints a commission to study regional integration, including intellectuals, economists, military reformers, and labor leaders. The commission is chaired by José Manuel Cortina, a respected jurist and diplomat, with members including Juan Bosch (Dominican exile and intellectual), Ramón Barquín (the military officer who helped stop Batista), and Fernando Ortiz (renowned anthropologist and scholar of Afro-Cuban culture).

The commission studies various models of regional cooperation: Bolívar’s failed Gran Colombia, the emerging European Common Market, federal systems like the United States and Switzerland, and even historical examples like the Hanseatic League. They face fundamental questions: Who should be included? What powers should the confederation have? How will decisions be made? What are the economic arrangements?

By early 1954, the commission produces a draft proposal for a Caribbean Confederation initially including Cuba, Haiti, and the Dominican Republic, with provisions for Puerto Rico to join once it achieves independence from the United States.

These four nations share crucial characteristics that make confederation plausible: geographic proximity in the Greater Antilles, shared colonial histories (all were Spanish colonies, with Haiti’s unique French period), common experiences with American intervention, sugar-based economies, racially mixed populations, and similar struggles with political instability. Cuba is the largest at 5.5 million people, followed by Haiti (3.5 million), the Dominican Republic (2 million), and Puerto Rico (2.2 million). While Cuba is the largest, it’s not so dominant that it would inevitably control the confederation.

The Treaty of Havana: Birth of the Confederation (1954)

Practical politics lead to a difficult compromise: the initial confederation includes only Cuba and Haiti, with the Dominican Republic excluded as long as Rafael Trujillo’s brutal dictatorship continues. Including Trujillo would undermine the confederation’s democratic legitimacy. Puerto Rico will be invited once it achieves independence.

The Treaty of Havana, signed on May 20, 1954—the 52nd anniversary of Cuban independence—creates the Caribbean Confederation with a bicameral Confederal Assembly (a Senate with equal representation and a Chamber of Representatives based on population), a Confederal Council composed of member state leaders, a Confederal Court, and a Secretariat headquartered in Havana.

Key provisions establish a free trade zone between members, freedom of movement for citizens, coordinated foreign policy, mutual defense commitments, and democratic standards that member states must maintain. Crucially, member states retain control over internal governance, education, culture, and most domestic policy. The confederation is explicitly not a unitary state but a partnership of sovereign nations.

The treaty is ratified by both Cuban and Haitian legislatures in June 1954, and the Caribbean Confederation officially begins on July 1, 1954.

Early Challenges: Making Confederation Work (1954-1960)

The confederation immediately faces enormous challenges. Cuba speaks Spanish; Haiti speaks Haitian Creole and French. Government proceedings require extensive translation. The solution makes Spanish, French, and Haitian Creole all official languages, with simultaneous translation provided—expensive and cumbersome but symbolically essential.

Economic integration proves equally difficult. Cuban and Haitian economies exist at vastly different development levels. Cuba has railroads, electricity, modern harbors, and industrial infrastructure; Haiti has minimal infrastructure, with most people engaged in subsistence agriculture. Free trade benefits Cuban manufacturers but threatens Haitian industry. Freedom of movement benefits Haitian workers but creates tension in Cuba.

The confederation establishes a Development Fund to invest in Haitian infrastructure: roads, ports, schools, clinics, electrical generation. The goal is reducing the development gap so integration benefits both nations rather than creating exploitation.

The United States watches the confederation with alarm. American officials see it as challenging U.S. hegemony in the Caribbean. The response includes diplomatic pressure, economic leverage through sugar quotas, support for Trujillo in the Dominican Republic as a bulwark against confederation expansion, propaganda portraying the confederation as communist-influenced, and CIA monitoring of confederation leaders.

Despite American pressure, the confederation survives. Cuban President Prío and Haitian President Paul Magloire become the confederation’s public faces, traveling between Havana and Port-au-Prince, giving speeches about Caribbean solidarity, and meeting foreign diplomats.

The confederation carefully avoids direct military intervention against Trujillo but supports Dominican opposition through Radio Free Dominican Republic (broadcasting from Cuba), providing haven for Dominican exiles, imposing economic sanctions, and diplomatic efforts at the OAS and UN highlighting Trujillo’s human rights abuses.

Trujillo’s Fall and Dominican Entry: 1960-1963

By 1960, Trujillo’s regime is weakening due to aging leadership (he’s 69), international isolation after the OAS imposes sanctions, economic strain, internal opposition, and wavering American support. On May 30, 1961, Trujillo is assassinated—as happened historically—but in our alternate timeline, the confederation is prepared.

Democratic exiles, particularly Juan Bosch, return immediately from Cuba and Haiti. The confederation provides diplomatic, economic, and technical support for democratic transition while carefully avoiding military intervention that might provoke American counter-intervention. After a difficult transitional period, elections are held in December 1961. Bosch wins decisively, running explicitly on confederation membership.

The Treaty of Santo Domingo, signed August 16, 1963, brings the Dominican Republic into the confederation as its third member. The confederation now includes nearly 13 million people with combined economic weight that gives it real influence in Caribbean affairs.

Puerto Rico’s Journey to Independence: 1954-1970

The confederation’s formation energizes Puerto Rican independence advocates. The Puerto Rican Independence Party (PIP) sees the confederation as a solution to the main objection against independence: economic isolation. Their message becomes: “Independence doesn’t mean isolation. Independence means joining the Caribbean Confederation—partnering with Cuba, Haiti, and the Dominican Republic to build a prosperous, sovereign Caribbean.”

This message resonates with nationalists seeking dignity and self-determination, labor unions seeing benefits in free movement, intellectuals attracted to Caribbean cultural space independent of American influence, and social justice advocates viewing confederation social policies as models.

The Dominican Republic’s 1963 entry electrifies Puerto Rican politics. The confederation is no longer an experiment—it’s a regional movement delivering measurable improvements. In 1964 Puerto Rican elections, the PIP performs its best ever, winning 25% of the vote. Polling shows that when asked specifically about independence within the confederation (rather than isolated independence), support rises to nearly 40%.

A referendum on Puerto Rico’s status is held July 23, 1967, offering three options: statehood, enhanced commonwealth, or independence with confederation membership. Results: Independence 43%, Enhanced Commonwealth 39%, Statehood 18%.

The U.S. government questions the result’s legitimacy, arguing such a momentous decision requires an absolute majority. But international pressure (particularly from UN decolonization committees), domestic American divisions (with civil rights and anti-war activists seeing parallels to denying Vietnamese self-determination), Puerto Rican mobilization through strikes and protests, and confederation commitments to support Puerto Rican independence eventually force Washington’s hand.

In August 1968, Congress passes the Puerto Rico Independence Act providing for independence effective January 1, 1970, with an 18-month transition period. The Treaty of San Juan, signed November 19, 1969 (anniversary of the Grito de Lares independence uprising), brings Puerto Rico into the confederation as its fourth member.

The Mature Confederation: 1970-1975

With four members and roughly 16 million people, the confederation reaches critical mass enabling more ambitious policies. The confederation pursues coordinated industrialization with different members specializing based on comparative advantages: Cuba in pharmaceuticals and heavy industry, Puerto Rico in electronics and light manufacturing, Dominican Republic in textiles and tourism, Haiti in assembly industries and agricultural processing.

Investment in education expands dramatically. The Caribbean University system offers free higher education across multiple campuses. Healthcare systems improve, with Cuban medical expertise combined with resources from wealthier members producing dramatic improvements in infant mortality, life expectancy, and disease rates.

Infrastructure integration connects the confederation physically through inter-island ferries, telecommunications networks, coordinated transportation, and a confederation airline. Social welfare programs provide pensions, unemployment insurance, disability benefits, and housing subsidies. Cultural development celebrates diversity while building common identity through festivals, confederation-wide media, sports leagues, and educational curricula teaching shared Caribbean history.

The confederation carefully navigates Cold War dangers through explicit non-alignment, refusing American and Soviet military alliances while maintaining diplomatic and economic relations with both blocs. Trade diversifies to include Western Europe, Eastern Europe, Latin America, Africa, and Asia. Military forces remain modest and defensive. Diplomatic activism in international organizations increases confederation standing.

By 1975, the confederation can point to significant achievements: sustained democratic governance, economic growth averaging 4-5% annually, dramatic improvements in education and healthcare, successful resistance to American destruction efforts, international recognition, and emergence of distinct confederation identity. Challenges persist: economic inequality between members, commodity export dependence, American hostility, internal political tensions, and the ongoing difficulty of building strong democratic institutions.

Why This Matters: Historical Lessons

This alternate history explores what might have been possible if Caribbean nations had successfully unified to resist external domination. It didn’t happen historically because American power was overwhelming, Caribbean nations had divergent interests and political cultures, leadership failures produced dictators rather than democratic reformers, Cold War dynamics made non-alignment nearly impossible, and sugar economies were so integrated with American markets that extrication seemed economically catastrophic.

But exploring this counterfactual helps us understand actual Caribbean history—and contemporary challenges. The confederation that never was suggests that solidarity, democracy, and regional cooperation remain viable pathways, even if difficult. By understanding what didn’t happen and why, we better grasp what did happen and what still might happen in futures yet to be written.

Teaching Applications

For educators using this counterfactual, consider these discussion frameworks:

Historical Contingency – Use the failed Batista coup as a case study in how small events can have large consequences. What specific factors would have needed to change for the coup to fail? How plausible are these changes?

Regional Integration – Compare the imagined Caribbean Confederation to actual integration efforts like the European Union, East African Community, or ASEAN. What factors contribute to successful regional cooperation? Why do some efforts fail?

Decolonization and Sovereignty – Examine how colonized or dominated peoples achieve genuine independence. What strategies work? What roles do external powers play in enabling or preventing self-determination?

Economic Development Models – Analyze the confederation’s development strategy (regional integration, import substitution, social investment) compared to alternatives. What are the trade-offs between different development paths?

Identity Formation – Discuss how the confederation might have built common identity while respecting linguistic, cultural, and national differences. What can we learn from this about contemporary challenges of diversity and unity?

The Caribbean Confederation exists only in imagination, but the aspirations it represents—dignity, sovereignty, solidarity, and hope—were and remain very real for Caribbean peoples continuing to grapple with legacies of colonialism and questions of whether small nations can chart independent paths in a world dominated by great powers.

While these events are not true they are based on historic fact and the possibility of one change in history. To read more of my Alternate History scenarios, be sure read here.