What If San Juan Developed Different Relationships with the US?

The Actual History

The relationship between San Juan (and Puerto Rico as a whole) and the United States began with the Spanish-American War of 1898. After four centuries of Spanish colonial rule, Puerto Rico was ceded to the United States under the Treaty of Paris. Unlike Cuba, which gained nominal independence following the war, Puerto Rico became an unincorporated territory of the United States—a status it maintains to this day, making it one of the world's oldest colonies.

The U.S. initially ruled Puerto Rico under military governance until the Foraker Act of 1900 established a civilian government with a governor appointed by the U.S. President. The 1917 Jones-Shafroth Act subsequently granted Puerto Ricans U.S. citizenship, though notably on the eve of American entry into World War I—timing that allowed for the conscription of Puerto Ricans into the U.S. military. Despite this conferral of citizenship, Puerto Ricans residing on the island could not vote in U.S. presidential elections and lacked voting representation in Congress.

A significant shift occurred in 1952 when Puerto Rico adopted its own constitution and became a Commonwealth, or "Estado Libre Asociado" (Free Associated State). This arrangement allowed Puerto Rico limited self-governance while remaining under U.S. sovereignty. Under Commonwealth status, Puerto Rico maintained its own elected government, legal system, and tax structure, while the U.S. retained control over defense, foreign relations, currency, and interstate commerce.

The political status of Puerto Rico has remained contentious throughout the decades since. Three primary options have dominated the discourse: continued Commonwealth status, statehood, or independence. Five status referendums have been held since 1967, with inconclusive or disputed results. The most recent votes in 2012, 2017, and 2020 showed majority support for statehood, though these referendums faced criticism regarding low turnout and disputed methodologies.

Economically, Puerto Rico has experienced a complex relationship with the mainland U.S. Until 2006, Section 936 of the U.S. tax code provided significant tax exemptions for U.S. corporations operating in Puerto Rico, which attracted pharmaceutical companies and manufacturers. The phasing out of these tax benefits between 1996 and 2006 contributed to economic decline. By 2015, Puerto Rico faced a severe debt crisis, with public debt exceeding $70 billion alongside an additional $49 billion in unfunded pension liabilities.

In 2016, the U.S. Congress passed PROMESA (Puerto Rico Oversight, Management, and Economic Stability Act), establishing a Financial Oversight and Management Board with authority over Puerto Rico's budget and fiscal policies. This board, whose members are appointed rather than elected, has implemented austerity measures that have proven deeply unpopular among many Puerto Ricans.

The vulnerability of Puerto Rico's status was starkly revealed in 2017 when Hurricane Maria devastated the island. The inadequate federal response highlighted the limitations of Puerto Rico's political relationship with the United States. The storm caused nearly 3,000 deaths and left the island without electricity for months. Then-President Trump's disparaging comments and reluctance to provide aid underscored the power imbalance inherent in the relationship.

Today in 2025, Puerto Rico remains an unincorporated U.S. territory. Its 3.2 million residents are U.S. citizens who cannot vote in presidential elections while residing on the island, have no voting representation in Congress, receive disparate treatment under federal programs, yet are subject to many federal laws. This status continues to fuel ongoing debates about democracy, decolonization, and self-determination.

The Point of Divergence

What if Puerto Rico had developed a fundamentally different relationship with the United States following the Spanish-American War? In this alternate timeline, we explore a scenario where the political, economic, and cultural ties between San Juan and Washington took a dramatically different course, reshaping not only Puerto Rico's destiny but potentially altering the geopolitical landscape of the entire Caribbean region.

The most plausible point of divergence occurs in the critical period between 1898 and 1900, when the United States was determining how to administer its newly acquired territories. In our timeline, the 1901 Insular Cases established the doctrine of "unincorporated territories"—possessions that were neither foreign countries nor fully integrated parts of the United States. This judicial innovation created a permanent colonial status for Puerto Rico.

Several alternative paths might have emerged:

First, Puerto Rico might have followed a path similar to Cuba, gaining formal independence while remaining under significant U.S. influence. The Teller Amendment, which prohibited U.S. annexation of Cuba, could conceivably have been extended to Puerto Rico had different political calculations prevailed in Washington or had Puerto Rican independence advocates wielded greater influence.

Alternatively, Puerto Rico might have been placed on an explicit path to statehood from the beginning, similar to Hawaii and Alaska, which were incorporated as territories before achieving statehood. This would have required American policymakers to view Puerto Rico's predominantly Hispanic, Spanish-speaking population differently than they did historically.

A third possibility involves a negotiated arrangement granting Puerto Rico greater autonomy while maintaining formal ties to the United States—something more substantive than the Commonwealth status eventually established in 1952, perhaps closer to the relationship between the United Kingdom and its Commonwealth realms or the freely associated states of Micronesia, the Marshall Islands, and Palau.

In our alternate timeline, we'll explore what might have transpired if, instead of implementing the Foraker Act of 1900 establishing unilateral American rule, the United States had engaged in substantive negotiations with Puerto Rican political leaders, resulting in a bilateral treaty that established Puerto Rico as a freely associated state—a sovereign nation with close ties to the United States but retaining control over its internal and many external affairs.

This divergence could have been prompted by several factors: stronger resistance to American colonization in Puerto Rico, different attitudes in the McKinley administration, greater influence of anti-imperialist voices in Congress, or perhaps even intervention by other world powers concerned about American expansion in the Caribbean.

Immediate Aftermath

A New Political Framework (1900-1910)

In this alternate timeline, rather than imposing the Foraker Act, the McKinley administration enters into negotiations with Puerto Rican political leaders in 1899. These negotiations culminate in the Treaty of San Juan of 1900, which establishes Puerto Rico as a sovereign republic with special ties to the United States. This arrangement, though unprecedented in American foreign relations at the time, emerges as a compromise between complete U.S. annexation and full independence.

The Treaty of San Juan includes several key provisions:

Recognition of Puerto Rican sovereignty and independence
A defensive alliance guaranteeing U.S. military protection
U.S. naval basing rights in San Juan harbor and Vieques
Preferential trade agreements benefiting both parties
A shared currency arrangement using the U.S. dollar
Free movement of people between Puerto Rico and the United States

Unlike in our timeline, Puerto Ricans do not receive U.S. citizenship in this scenario. Instead, they maintain Puerto Rican citizenship while enjoying special immigration status that allows them to live and work in the United States without restriction—a privilege not extended to citizens of other foreign nations.

The first presidential election in the newly sovereign Puerto Rico takes place in 1901, with Luis Muñoz Rivera, who had negotiated greater autonomy from Spain just before the Spanish-American War, emerging as the country's first democratically elected president. His Republican Party (not affiliated with the U.S. party of the same name) campaigns on a platform of modernizing Puerto Rico while maintaining its Hispanic cultural identity.

Economic Development on Different Terms (1900-1920)

Economically, sovereign Puerto Rico charts a different course than in our timeline. Without the restrictions of the U.S. coastwise shipping laws (which in our timeline required all goods shipped between U.S. ports to use American vessels), Puerto Rico develops more diverse trading relationships. While the United States remains its largest trading partner, the island establishes significant commercial ties with other Caribbean nations, Latin America, and Europe.

The Puerto Rican government implements policies to diversify beyond the sugar monoculture that dominated under Spanish and early American rule. Coffee cultivation, once a major export under Spanish rule but neglected under American administration in our timeline, receives substantial government support. Puerto Rico also develops light manufacturing earlier than in our timeline, attracting investment from European firms seeking access to American markets through Puerto Rico's preferential trade agreement with the U.S.

San Juan experiences rapid development as the capital of a sovereign nation rather than merely an American colonial administrative center. The city expands its port facilities to accommodate increased international trade and establishes diplomatic missions from various nations. The architecture of San Juan's newer districts reflects this international orientation, incorporating Spanish, American, and Caribbean influences into a distinctive Puerto Rican style.

Regional Implications (1900-1920)

Puerto Rico's unique status has significant implications for the wider Caribbean. Cuba, which gained nominal independence from the United States in 1902 but remained under heavy American influence through the Platt Amendment, looks to Puerto Rico's more advantageous arrangement as a model. Cuban nationalists push for renegotiation of Cuba's relationship with the United States, leading to tensions that culminate in the Cuban Constitutional Crisis of 1908, where the U.S. is forced to make concessions to prevent outright rebellion.

The Dominican Republic, which experienced U.S. military occupation from 1916-1924 in our timeline, finds itself in a different position in this alternate history. Puerto Rico serves as an intermediary between the Dominican Republic and the United States, helping broker an agreement that prevents direct U.S. military intervention while addressing American concerns about European influence and debt repayment.

World War I and Its Aftermath (1914-1920)

When World War I erupts in 1914, Puerto Rico declares neutrality but maintains its close relationship with the United States. After the U.S. enters the war in 1917, Puerto Rico—though not obligated by treaty to join the conflict—voluntarily permits increased American military use of its ports and volunteers Puerto Rican regiments to serve alongside American forces.

This voluntary cooperation, contrasting with the conscription of Puerto Ricans as U.S. citizens in our timeline, generates significant goodwill in Washington. Following the war, President Woodrow Wilson invites Puerto Rico to join the newly formed League of Nations as a founding member—a symbol of the island's sovereign status despite its close ties to the United States.

The lack of U.S. citizenship and direct federal taxation means Puerto Ricans avoid Prohibition (1920-1933), allowing San Juan to develop as a popular destination for American tourists seeking legal alcohol. This tourism boom accelerates the development of hotels, restaurants, and entertainment venues in the capital, bringing additional prosperity but also social tensions related to the alcohol trade and associated activities.

Long-term Impact

The Great Depression and New Deal Era (1929-1945)

When the Great Depression strikes in 1929, sovereign Puerto Rico initially faces severe economic challenges without direct access to U.S. federal relief programs. However, this crisis prompts the development of a more self-sufficient and diversified economy than emerged in our timeline. President Teodoro Moscoso (1928-1936) implements a "Puerto Rican New Deal" that establishes cooperatives, public works, and small-scale industrialization initiatives financed primarily through partnerships with private capital rather than government spending.

The Puerto Rican government negotiates a modified extension of certain U.S. New Deal programs, emphasizing that while Puerto Rico remains sovereign, the special relationship between the two nations justifies economic cooperation during the crisis. This sets an important precedent for future economic relations.

By the late 1930s, Puerto Rico has weathered the Depression with less damage than many fully independent Caribbean nations, while maintaining greater economic autonomy than it possessed as a U.S. territory in our timeline. The country begins developing a distinctive "middle path" economic model that combines elements of state planning, private enterprise, and international trade.

World War II and the Post-War Order (1939-1960)

Puerto Rico again declares neutrality at the outbreak of World War II but rapidly allies with the United States following the Pearl Harbor attack in December 1941. Unlike in our timeline, where Puerto Ricans served as U.S. citizens in integrated units, the sovereign Puerto Rico sends its own military contingents to fight alongside American forces, primarily in the European theater.

The Puerto Rican air base at Borinquen (later Ramey Air Force Base in our timeline) becomes a critical Allied facility for anti-submarine warfare in the Caribbean, operated jointly by Puerto Rican and U.S. personnel. San Juan serves as a major port for convoys assembling to cross the Atlantic.

In the post-war period, Puerto Rico becomes a founding member of the United Nations in 1945 and joins the Organization of American States in 1948. The country positions itself diplomatically as a bridge between the United States and Latin America, often mediating in disputes between the U.S. and its southern neighbors.

Economic Transformation and the "Puerto Rican Model" (1950-1980)

The 1950s and 1960s see Puerto Rico develop what becomes known internationally as the "Puerto Rican Model" of development—a strategy that leverages the island's unique relationship with the United States while maintaining policy autonomy. Rather than the "Operation Bootstrap" industrialization program of our timeline, which relied heavily on U.S. tax exemptions, sovereign Puerto Rico implements a more balanced approach:

Negotiated preferential access to U.S. markets without full integration
Development of strong educational institutions, particularly in engineering, medicine, and business
Early investment in tourism infrastructure beyond just San Juan
Strategic development of light manufacturing and pharmaceutical industries
Maintenance of a strong agricultural sector, unlike the decline seen in our timeline
Development of San Juan as an international banking center with advantageous tax laws

By 1970, Puerto Rico achieves a level of prosperity unprecedented among Caribbean nations, with per capita income significantly higher than in our timeline. San Juan emerges as a truly international city, with strong commercial and cultural ties throughout the Americas and Europe.

The Cold War Context (1960-1990)

Puerto Rico's unique status poses interesting challenges during the Cold War. While firmly in the Western camp and maintaining its special relationship with the United States, sovereign Puerto Rico asserts greater diplomatic independence than it could as a U.S. territory. The country establishes diplomatic relations with various non-aligned nations and even cautiously engages with Cuba following the Cuban Revolution—serving occasionally as an unofficial backchannel between Havana and Washington.

This independent stance sometimes creates tensions with the United States, particularly during the Reagan administration, which views Puerto Rico's diplomatic outreach to leftist Latin American governments with suspicion. However, Puerto Rico's consistently democratic governance and market-oriented economy prevent any serious rupture in relations.

The Cuban Missile Crisis unfolds differently in this timeline. Puerto Rico's established diplomatic channels with Cuba allow for additional backchannel communications that complement the official U.S.-Soviet negotiations. President Roberto Sánchez Vilella of Puerto Rico plays a small but significant role in deescalating tensions through these unofficial channels.

Contemporary Era (1990-2025)

The end of the Cold War ushers in new opportunities and challenges for Puerto Rico. Without the limitations imposed by territorial status, Puerto Rico aggressively pursues economic integration with both North and South America. The country becomes an early and enthusiastic participant in regional trade agreements, positioning itself as a key link in hemispheric commerce.

San Juan develops into one of the Caribbean's premier financial centers, leveraging its unique position between Anglo and Latin American business cultures. The University of Puerto Rico, freed from the constraints of territorial status funding limitations, emerges as one of Latin America's leading research institutions, particularly in tropical medicine, renewable energy, and marine sciences.

By 2025, Puerto Rico has a population of approximately 4 million—larger than in our timeline due to less outmigration—and enjoys a standard of living comparable to Southern European nations. While maintaining its special relationship with the United States through the periodically updated Treaty of San Juan (most recently renegotiated in 2021), Puerto Rico has diversified its international ties considerably.

The Puerto Rican passport is among the world's most valuable, offering visa-free access to both the United States and the European Union (the latter through special agreements negotiated in the 2000s). The Puerto Rican diaspora, though smaller than in our timeline, maintains strong connections to the island, facilitated by the continued free movement provisions with the U.S.

Cultural Impact

Perhaps the most profound long-term difference in this alternate timeline is cultural. Without the complex identity questions posed by territorial status, Puerto Rican culture develops with greater confidence in its distinctive character. Spanish remains the dominant language, though English is widely spoken. Puerto Rican literature, music, and art achieve international recognition earlier and more extensively than in our timeline.

San Juan establishes itself as a cultural capital of the Spanish-speaking Caribbean, hosting major international festivals, sporting events, and academic conferences. The historic district of Old San Juan, managed under sovereign Puerto Rican preservation laws rather than U.S. National Park Service guidelines, develops somewhat differently—maintaining more authentic local character while still accommodating tourism.

Puerto Rican sovereignty allows for earlier and more extensive cultivation of national pride through institutions like the Olympic Committee (established 1948) and national sports leagues. The Puerto Rican national football (soccer) team becomes a regional powerhouse by the 1990s, while baseball remains the most popular sport with a thriving professional league that serves as a talent pipeline to Major League Baseball.

Expert Opinions

Dr. Jorge Duany, Professor of Caribbean Studies at Florida International University, offers this perspective: "The territorial relationship between Puerto Rico and the United States created a profound status dilemma that has dominated the island's politics for generations. In an alternate timeline where Puerto Rico established sovereignty while maintaining close U.S. ties, we might have seen a very different political landscape emerge—one focused more on substantive policy issues rather than the perpetual status debate. This arrangement would have allowed Puerto Rico to develop its own national institutions while still benefiting from economic and security connections to the United States. The psychological impact of self-governance should not be underestimated; it fundamentally changes how a society views itself and its possibilities."

Dr. Elena Martínez, Economic Historian at the University of California, Berkeley, suggests: "Puerto Rico's economic development was profoundly shaped by its territorial status, creating both opportunities and severe constraints. The tax benefits attracted certain industries but discouraged others, while Section 936 created an artificial economy that collapsed when the benefits were withdrawn. A sovereign Puerto Rico with negotiated economic ties might have developed a more balanced, resilient economy with greater local ownership and entrepreneurship. We'd likely see a smaller wealth gap between Puerto Rico and the mainland U.S. in such a scenario, though I doubt Puerto Rico would have matched countries like Singapore in economic performance given its size and resource constraints. The critical difference would be economic sovereignty—the ability to create policies tailored to local conditions rather than being subject to policies designed primarily for the continental United States."

Dr. Antonio Fernández, Professor of International Relations at Universidad Complutense de Madrid, argues: "A sovereign Puerto Rico would have significantly altered Caribbean geopolitics during the Cold War and beyond. As a Spanish-speaking democracy with close U.S. ties but its own foreign policy, Puerto Rico could have served as a diplomatic bridge between Latin America and the United States in ways that were impossible under territorial status. We might have seen earlier resolution of certain regional conflicts and potentially different outcomes in places like Nicaragua and Venezuela where cultural and linguistic barriers complicated U.S. policy. The ripple effects would extend to migration patterns, regional economic integration, and possibly even the development of democracy throughout Latin America, as Puerto Rico could have provided an alternative model to both American-imposed regimes and anti-American revolutionary movements."