What If Havana Developed Without US Embargo?

The Actual History

The story of the US embargo against Cuba begins with the Cuban Revolution of 1959, when Fidel Castro and his revolutionary forces overthrew the US-backed dictator Fulgencio Batista. In the years leading up to the revolution, Havana had become a playground for wealthy Americans, with US businesses and organized crime syndicates maintaining significant control over Cuba's economy. American corporations owned 70% of Cuba's arable land and dominated key industries including utilities, mining, and sugar production.

Following Castro's rise to power, relations between Cuba and the United States rapidly deteriorated. Castro's government began nationalizing American-owned businesses and properties without compensation. In response, President Eisenhower reduced the Cuban sugar quota by 95% in July 1960. When Cuba turned to the Soviet Union for economic support, Cold War tensions escalated. In October 1960, the Eisenhower administration imposed the first comprehensive trade embargo on exports to Cuba, except for food and medicine.

The situation worsened in 1961 with the failed Bay of Pigs invasion, an unsuccessful attempt by CIA-trained Cuban exiles to overthrow Castro. Relations hit their nadir during the Cuban Missile Crisis of October 1962, when the US discovered Soviet nuclear missiles installed in Cuba, bringing the world to the brink of nuclear war. On February 7, 1962, President Kennedy formalized and expanded the embargo through Proclamation 3447, establishing a near-total economic embargo that prohibited virtually all trade between the United States and Cuba.

Over the decades, the embargo was strengthened through additional legislation. The Cuban Democracy Act of 1992 prohibited foreign-based subsidiaries of US companies from trading with Cuba, and the Helms-Burton Act of 1996 penalized foreign companies doing business in Cuba. The embargo severely restricted Cuba's access to markets, financing, and technology, forcing the island nation to rely heavily on Soviet support until the USSR's collapse in 1991.

Havana, once the "Paris of the Caribbean," experienced significant economic hardship under the embargo. The city's infrastructure deteriorated as buildings crumbled without resources for maintenance. The period following the Soviet collapse, known as the "Special Period," saw severe shortages of food, fuel, and basic goods. Vintage American cars from the pre-revolution era became iconic symbols of Cuba, preserved out of necessity rather than nostalgia.

By the early 21st century, Havana showed a stark contrast of architectural beauty and decay. Despite Castro's emphasis on universal education and healthcare, economic opportunities remained limited. Tourism became an important economic lifeline after the Special Period, though it was primarily from Canada, Europe, and Latin America rather than the United States.

Under President Obama, diplomatic relations were partially restored in 2015, with the reopening of embassies and some easing of travel restrictions. However, the Trump administration later reversed many of these policies, and the core economic embargo remained in place. As of 2025, despite calls from the international community (the UN General Assembly has condemned the embargo annually since 1992), the embargo continues, having now lasted for over 60 years — the longest-lasting trade embargo in modern history.

The Point of Divergence

What if the United States had never imposed an economic embargo on Cuba? In this alternate timeline, we explore a scenario where American policy toward revolutionary Cuba took a dramatically different path, allowing Havana to develop without the crushing economic isolation it experienced in our timeline.

The point of divergence could have occurred in several plausible ways. One possibility centers on the Eisenhower administration's response to Castro's revolution in 1959-1960. Instead of the escalating economic pressure that culminated in the initial trade restrictions of October 1960, the US government might have adopted a more pragmatic approach, recognizing Castro's popular support while attempting to maintain economic ties to prevent Soviet influence.

Alternatively, the divergence could have happened during the Kennedy administration. Following the failed Bay of Pigs invasion and the Cuban Missile Crisis, Kennedy might have concluded that economic engagement rather than isolation would more effectively influence Cuba's trajectory. Rather than formalizing and expanding the embargo in February 1962, Kennedy could have negotiated a settlement that addressed security concerns while preserving economic ties.

A third possibility involves President Johnson, who might have reevaluated Cuban policy after Kennedy's assassination, determining that the embargo had failed to weaken Castro's position and instead pushed Cuba further into the Soviet orbit. Johnson, focused on his domestic "Great Society" programs and the escalating Vietnam War, might have seen normalization with Cuba as a way to reduce Cold War tensions in America's backyard.

The most plausible scenario combines elements of these possibilities: after the resolution of the Cuban Missile Crisis, Kennedy might have recognized an opportunity to reset relations. In this alternate timeline, Kennedy survives the assassination attempt in November 1963 and uses his second term to gradually normalize relations with Cuba, treating Castro's government as another nationalist regime to be engaged with rather than isolated. The negotiations would likely include agreements about Soviet military presence, compensation for nationalized American assets, and gradual political reforms in Cuba.

This approach would have reflected Kennedy's evolving thinking on Cold War conflicts. His American University "Peace Speech" of June 1963 had already signaled a willingness to find accommodation with communist nations. Applying this philosophy to Cuba would have represented a bold but logical extension of Kennedy's foreign policy vision.

Immediate Aftermath

Geopolitical Rebalancing (1964-1968)

The absence of a formalized embargo would have immediately altered the geopolitical dynamic in the Caribbean. While Cuba would have maintained its alliance with the Soviet Union, the relationship would have been less dependent and exclusive. Castro, a pragmatic revolutionary despite his Marxist rhetoric, would have benefited from maintaining economic ties with both superpowers, playing them against each other to maximize Cuba's advantage.

The Kennedy administration would have faced significant domestic political backlash, particularly from Cuban exile communities in Florida and hardline anti-communist politicians. However, Kennedy could have framed this policy as a strategic victory that prevented Cuba from becoming a Soviet satellite while preserving American influence. The anticipated economic benefits for American businesses would have helped blunt criticism from the business community.

Soviet leader Nikita Khrushchev, who had already shown his willingness to compromise during the Missile Crisis, would have likely accepted this new arrangement. The USSR would continue providing military and economic aid to Cuba but at reduced levels, relieved that the financial burden of supporting Cuba entirely would not fall solely on Moscow.

Economic Recovery and Diversification (1965-1970)

Havana would have experienced an immediate economic boost from continued access to American markets, technology, and tourism. The city's port facilities would have been modernized to handle increased trade volume. American companies would have negotiated new terms for operating in Cuba, likely accepting partial Cuban government ownership in exchange for continued presence in the market.

Castro's government would have implemented a hybrid economic model—maintaining state control over key sectors like healthcare, education, and major industries while allowing private enterprise and foreign investment in others. This "Cuban model" would have resembled Yugoslavia's market socialism more than the rigid Soviet system.

Agricultural reforms would have continued but with greater access to modern farming equipment and techniques from the US. Cuba's sugar industry would have diversified earlier, with increased production of citrus fruits, tobacco, and coffee for export markets. American agricultural experts would have worked alongside Cuban farmers to improve productivity while maintaining the revolutionary government's commitment to land reform.

Tourism would have developed in a more balanced way, with American visitors contributing significantly to the economy without dominating it as they had before the revolution. The Cuban government would have regulated tourism development to prevent the return of the pre-revolutionary casino culture and its associated social problems.

Social Programs Without Extreme Austerity (1965-1975)

One of the most significant differences would have been in how Cuba implemented its ambitious social programs. In our timeline, Cuba achieved impressive results in healthcare and education but at the cost of severe austerity in other areas. With continued economic engagement with the US, Castro would have had more resources to fund these programs without forcing such extreme sacrifices.

Havana's medical facilities would have benefited from access to American medical technology while maintaining Cuba's emphasis on preventive care and universal access. The renowned Latin American School of Medicine would have been established earlier, becoming a center for medical innovation that combined Cuban approaches to public health with advanced medical technologies.

Housing development in Havana would have proceeded more rapidly, with a mix of state-built affordable housing and private development. The colonial architecture of Old Havana would have been preserved and restored earlier, avoiding the severe deterioration seen in our timeline.

Diplomatic Position (1968-1975)

By the late 1960s, Cuba would have occupied a unique diplomatic position—a socialist state maintaining relations with both the Soviet bloc and the United States. This arrangement would have given Cuba outsized diplomatic influence relative to its size, allowing it to help mediate conflicts between East and West.

Castro would have positioned Cuba as a leader among non-aligned nations while maintaining his revolutionary credentials through support for independence movements in Africa and Latin America. However, this support would have been more diplomatic and less military in nature than in our timeline, as Cuba balanced its revolutionary principles with pragmatic international relationships.

Long-term Impact

Havana as a Caribbean Economic Hub (1975-1990)

Without the constraints of the embargo, Havana would have developed into the preeminent economic center of the Caribbean by the 1980s. The city's natural deep-water harbor, strategic location, and educated workforce would have made it an ideal regional hub for trade, finance, and services.

Economic Development Model

Cuba would have developed a distinctive economic model that combined elements of state planning with market mechanisms—similar to what China later implemented but with greater emphasis on social welfare. Key features would have included:

State control of strategic industries (energy, mining, transportation)
Mixed ownership in manufacturing and agriculture
Encouragement of small and medium private enterprises in retail, services, and tourism
Special economic zones to attract foreign investment
Comprehensive social welfare programs funded by tax revenues

This hybrid approach would have delivered more balanced economic growth than either the capitalist model of other Caribbean nations or the strict command economy Cuba adopted in our timeline. By 1990, Cuba's GDP per capita might have reached levels comparable to Costa Rica or Panama—approximately $5,000-$6,000 in 1990 dollars.

Infrastructure and Urban Development

Havana's infrastructure would have developed continuously rather than stagnating. By the 1980s, the city would have featured:

A modernized port capable of handling container shipping
An expanded José Martí International Airport serving as a regional transportation hub
Reliable electrical grid powered by a mix of conventional and renewable energy
Modern telecommunications network implemented with joint US-European-Soviet technology
Expanded public transportation system including a metro system begun in the late 1980s
Preserved historical districts alongside modern development

The absence of the embargo would have prevented the severe deterioration of Havana's building stock. Instead of crumbling facades and collapsing structures, Old Havana would have undergone systematic preservation and restoration beginning in the 1970s, similar to historic districts in European cities.

Political Evolution (1975-2000)

Cuba's political system would have evolved gradually as economic liberalization created pressure for political reforms. Fidel Castro would have maintained leadership but adapted his governing approach as circumstances changed.

By the 1980s, Cuba might have implemented a political system combining one-party socialist governance with greater local democratic participation and limited political pluralism. Opposition parties might not have been permitted, but within the Cuban Communist Party, different factions would have emerged representing various ideological tendencies from orthodox Marxism to social democracy.

The collapse of the Soviet Union in 1991 would have been less traumatic for Cuba than in our timeline. Without total dependence on Soviet aid, Cuba would have been better positioned to weather the transition. Rather than the catastrophic "Special Period" of the 1990s, Cuba would have experienced a challenging but manageable economic readjustment.

As Castro aged, a more institutionalized succession process would have emerged. Rather than simply handing power to his brother Raúl as occurred in our timeline, a collective leadership model might have developed with representatives from different factions within the party.

Cultural Renaissance (1980-2010)

Havana's cultural scene would have flourished with exposure to international influences while maintaining its distinctive Cuban character. The city would have become a global cultural center, particularly in music, dance, visual arts, and literature.

Cuban music would have evolved in fascinating directions, with traditional forms like son and rumba blending with jazz, rock, hip-hop, and electronic music earlier and more extensively than in our timeline. Havana would have hosted major international music festivals drawing artists and audiences from around the world.

Cuban cinema would have developed into one of the most significant national film industries in Latin America, with Havana hosting an internationally renowned film festival. With access to modern filmmaking technology and international distribution, Cuban filmmakers would have found global audiences while maintaining their distinctive storytelling traditions.

The arts would have benefited from Cuba's unique position between capitalism and socialism. State support for culture would have continued, but artists would have gained access to international markets and audiences without the restrictions imposed by the embargo.

Technological Development and Innovation (1990-2025)

With access to global technology markets, Cuba would have leveraged its excellent education system to develop significant technology capabilities. By the early 2000s, Havana would have emerged as a technology hub for the Caribbean and Latin America.

Cuba's strong tradition in medical research would have expanded into biotechnology and pharmaceuticals earlier and more extensively than in our timeline. Without embargo restrictions, Cuban medical innovations would have readily entered the global market, potentially making significant contributions to treatments for diseases common in tropical and developing regions.

The internet and digital revolution would have arrived in Cuba without the delays experienced in our timeline. By the late 1990s, Cuba would have developed significant digital infrastructure, and by the 2010s might have established itself as a regional center for software development, digital content creation, and IT services.

Cuba's agricultural sector would have benefited from continued access to global agricultural technology. The country would have likely become a leader in sustainable tropical agriculture, developing innovative farming techniques that balanced productivity with environmental protection.

Havana in 2025: A Counterfactual Present

By 2025 in this alternate timeline, Havana would be a city of approximately 3-3.5 million people, larger than in our timeline due to greater economic opportunity reducing emigration. The city would feature a striking blend of restored colonial architecture, mid-century modernism, and contemporary design.

Economically, Havana would function as the financial and commercial capital of the Caribbean, hosting regional headquarters for multinational corporations, international organizations, and financial institutions. The city's GDP per capita would likely approach $18,000-$20,000, placing it among the more prosperous urban centers in Latin America.

Politically, Cuba would have evolved into a more open system while maintaining its distinctive socialist character. The Communist Party would still hold a dominant position, but with internal democratic processes and tolerance for limited opposition. Civil liberties would have expanded gradually, with greater freedom of expression and association than in our timeline.

Havana's cultural scene would be globally recognized for its vibrancy and innovation. The city would regularly host international events in music, film, art, and literature, drawing cultural tourists from around the world.

Environmental sustainability would likely be a priority, with Cuba leveraging its educated population to develop green technologies suited to tropical island environments. Havana might be recognized as a pioneer in urban sustainability among developing nations.

The most striking difference would be in the relationship between Havana and Miami. Rather than being divided by politics and the embargo, the two cities would have developed a complementary relationship, with frequent business, cultural, and personal exchanges. They might function almost as twin cities across the Florida Strait, each with its distinctive character but deeply connected economically and culturally.

Expert Opinions

Dr. Jorge Domínguez, Professor Emeritus of International Relations at Harvard University, offers this perspective: "The US embargo fundamentally shaped Cuba's development trajectory, forcing it into extreme dependence on the Soviet Union. Without the embargo, Cuba would have certainly maintained its revolutionary government and socialist principles, but with the pragmatism that has always characterized Castro's actual governance when given room to maneuver. The resulting hybrid system would have produced a fascinating alternative model of development—neither capitalist nor Soviet-style communist, but a distinctively Cuban version of socialism with much greater economic dynamism and somewhat greater political pluralism. Havana today might look more like a Latin American Singapore than the time capsule it has become."

Dr. Carmelo Mesa-Lago, Distinguished Service Professor Emeritus of Economics at the University of Pittsburgh, provides this analysis: "The economic cost of the embargo to Cuba has been enormous—over $1 trillion by some estimates when factoring in six decades of foregone development. Without the embargo, Cuba's economic policies would still have created inefficiencies due to excessive centralization and ideological rigidity, but the magnitude would have been far less severe. Cuba's social achievements in healthcare and education would have been complemented by much stronger economic performance, potentially creating a more balanced development model that other Latin American nations might have sought to emulate. The 'Special Period' of the 1990s, which caused immense suffering and reversed many social gains, would have been largely avoided."

María Fernández-Rodríguez, Director of the Center for Cuban Studies in an alternate 2025, suggests: "The cultural impact of an open Cuba would have been profound on both sides of the Florida Strait. Cuban arts and culture would have influenced American society more directly and continuously, while Cubans would have had greater access to global cultural trends. The Cuban diaspora would look entirely different—smaller, less politically conservative, and maintaining much stronger ties to the island. Rather than the politically charged exile community that developed in Miami, we might have seen a more fluid movement of people between Cuba and the US, with many Cubans spending time in both countries for education, work, or family reasons. The cultural boundaries between Cuban and Cuban-American identity would have been much more permeable."