Transforming US-Cuba Relations: A Transactional Path to National Security

The relationship between the United States and Cuba is positioned for a significant shift, moving away from decades of “gray zone” operations toward a transactional diplomatic relationship focused on U.S. Homeland security.

The primary objective for the United States in this transition is the removal of Russian and Chinese intelligence and security presences from the island. By prioritizing national security over forced regime change, the U.S. May be able to secure its borders and supply chains while addressing the long-standing presence of foreign adversaries in the Western Hemisphere.

Defining Gray Zone Activity

Since 1959, U.S.-Cuban relations have been characterized by gray zone operations—activities that remain below the threshold of direct armed conflict but are used to achieve political or security goals.

In July 2024, the National Intelligence Council defined gray zone activity as:

The deliberate use of coercive or subversive instruments of power by, or on behalf of, a state to achieve its political or security goals at the expense of others, in ways that exceed or exploit gaps in international norms but are intended to remain below the perceived threshold for direct armed conflict. Gray zone campaigns are commonly characterized by a sustained, multi-domain approach, indirect methods, and deliberate ambiguity about their aims and sponsorship.

National Intelligence Council

Following the rise of Fidel Castro in 1959, Cuba utilized these methods by supporting global revolutions and leading the nonaligned movement. The Cuban government exported medical education and doctors to Africa and Latin America, using these programs to spread pro-communist propaganda alongside healthcare services.

Cuba served as a listening post for U.S. Adversaries, a dynamic exemplified by the Cuban missile crisis.

Evolution of U.S. Policy

The United States has employed various strategies toward Cuba over several decades. President Bill Clinton signed the Cuban Liberty and Democratic Solidarity Act, which tightened the embargo and established strict conditions for lifting sanctions.

President Barack Obama later shifted toward normalization, restoring diplomatic ties, relaxing some economic sanctions, and removing Cuba from the list of state sponsors of terrorism. During this period, Secretary of State John Kerry stated that the Monroe Doctrine was dead, which facilitated an increase in U.S. Tourism to the island.

This trajectory changed in 2017 when President Trump rolled back normalization efforts and implemented more than 240 measures to tighten sanctions.

Recent actions by the current administration include the implementation of a blockade and the arrest of President Maduro in Venezuela, a close supporter of Cuba. On January 29, 2026, President Trump signed an executive order citing that Cuba hosts Russia’s largest overseas signals intelligence facility and continues to build defense cooperation with the People’s Republic of China (PRC).

The January 29 order also alleged that Cuba provides a safe environment for transnational terrorist groups, including Hamas and Hizballah, to build regional ties. This was followed by another executive order on May 1, 2026, which further strengthened sanctions against Cuban leaders and reiterated concerns regarding Hizballah.

Cuba’s Internal Crisis and Strategic Culture

While maintaining its security relationships with U.S. Adversaries, the Cuban government has overseen a severe humanitarian crisis. The nation is currently facing electrical grid failures, the closure of schools and businesses, and the cancellation of surgeries in hospitals.

In recent years, nearly 3 million people have left Cuba. The Cuban military and intelligence services, once highly regarded, are now reported to be hollowed out and plagued by corruption.

Understanding how to navigate this crisis requires an analysis of Cuba’s “strategic culture”—the combination of historical, cultural, and political influences that shape how a state behaves internationally. A 2009 report from Florida International University (FIU) identified several key traits of Cuban strategic culture:

• The culture is nationalist, offensive, and deeply wary of U.S. Intentions.
• The ruling elite rose to power through anti-U.S. Sentiment and have experienced firsthand efforts by the U.S. To undermine their government.
• Any change in regime must be a Cuban-led affair.
• To alter the relationship, the U.S. Must reduce the sense of threat ingrained in the elite’s strategic culture.

A Transactional Path Forward

Given these factors, a strategy of forced regime change is viewed as unrealistic. Instead, a transactional approach to diplomacy may be more effective. This involves appealing to the economic needs of the Cuban elite while avoiding inflammatory or coercive language.

The most achievable victory for the U.S. Is in the national security sphere. By demanding that Havana remove Russian and Chinese intelligence presences, the U.S. Could secure its own supply chains and protect military bases and combatant commands located in Florida.

While Cuba offers limited economic gain due to its small market and degraded infrastructure, the strategic benefit of removing adversary listening posts from the U.S. Border is significant. A humanitarian victory may also follow through increased information freedom, though a full sea change in how the regime treats its citizens may take a generation to realize.