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U.S.-Cuban Relations: The Prospect of Future Political and Defense Alignment

The past month has facilitated events that, for the first time in 55 years, have allowed U.S. policymakers to seriously contemplate the prospect of radically reconstructing its foreign policy disposition towards the Cuban government. But, assuming any change at all occurs in the long run, the nature of the change beginning with the release of Alan Gross remains nebulous. To this end, the following exposition surveys and analyzes the following elements:

  • A brief recounting of the historical relationship, largely adversarial, between the two governments from 1960 to the present day.
  • Recent positive shifts in human rights and economics.
  • Cuba’s current economic, political and defense relationship with another regional neighbor, Venezuela.
  • How the aforementioned conditions may have a bearing on the future of political and defense alignments in the Western Hemisphere and beyond.

Historical Context

The United States began its relationship with Cuba when it defeated Spain in 1898 and took complete control over the island. Shortly afterwards, the US granted the island partial independence with the passage of the Platt Amendment in 1902. In 1934, the US granted official independence after supervising the island nation’s first national elections, in which Jose Miguel Gomez was elected the first president. Since then, the U.S. government has directly intervened in domestic Cuban conflicts several times. The pre-WWII relationship directly influenced interactions between the two nations in the latter half of the 20th Century.

In 1959, Fidel Castro, fierce Cuban nationalist and dogmatic Marxist-Leninist, led a renewed and successful revolt against the Batista regime. Under Castro, Cuba became a one party socialist state with neo-Stalinist tendencies. The clash in political ideologies between the U.S. and Cuba became immediately apparent. President Nixon returned from meeting with Castro distraught at the turn the nation had taken under its new leader, but was determined to work with him towards a more democratic position. In 1960, hopes for such an outcome seemed unlikely, as Castro nationalized all U.S. business in country without compensation, and began to institute economic reforms which included increased tariffs on U.S. imports while simultaneously making stronger trade arrangements with Moscow. Washington responded in kind by cutting off diplomatic relations and instituting an embargo on all trade to the island. This embargo became fully actualized during the Kennedy administration.

The U.S. government’s apparent ease in reverting to its previous modus operandi concerning Cuba resurfaced in 1961 during the Bay of Pigs. The revelation of the CIA’s failed attempt to sabotage the regime only served to solidify an already turbulent rapport, as the declaration of political alignment with the USSR followed soon after. The resulting distrust and ill will caused by the operation pushed Castro’s agreement to align his nation militarily with the Soviet Union. The subsequent events came to a climax in October 1962 when the U.S. discovered plans to install Soviet missile bases on Cuban soil. The infamous Missile Crisis ensued, ending more than two weeks later with U.S. capitulating to stipulations by both Cuba – to not invade again – and the USSR – to remove its missiles from Turkey.

Interestingly, political and military alignment with the Soviet Union in the 1960s began with a profitable economic relationship. This economic relationship led to a political relationship, which was followed even more swiftly by a defense relationship. While it is true that the political alignment between the USSR and Cuba was already well established the moment Castro seized power, the gateway to further agreement and collaboration on military objectives occurred after establishing economic ties.

From the missile crisis to today, the United States has kept Cuba in a state of ceaseless economic and diplomatic exile. In the early-mid 1990s, the U.S. explicitly coupled its economic embargos with its own provisios outlined in the Cuba Democracy Act and the Helms-burton Act. These qualified Cuba’s future inclusion, stating that it would not establish relations with Havana until it agreed to adopt a democracy that holds fair elections and excludes the Castro family from positions within it.

Of note, the Bay of Pigs invasion was not the only subversive ploy the U.S. attempted. Over the past two decades USAID has spearheaded “social outreach” initiatives. One such initiative included delivering telecom equipment to select communities throughout the island, an activity which led the Cuban government to accuse Alan Gross of attempting to undermine the government, leading to his incarceration in 2009. Another alleged operation included the promotion and fueling of Cuban music artists and rappers that opposed the country’s political ideology; an operation that lead to several interrogations before ending in failure.

While Cubans viewed the US with distrust following these intrusions, they were not the only factor contributing to Cuba’s diplomatic and political attitude. Geography is also an implicit factor in the Cuban domestic and international climate. Cuba’s Caribbean solitude feeds a perpetual mentality of isolation, which, coupled with a political ideology not shared by the majority of its neighbors, may have contributed to its defensive and hostile attitude to nations that present an existential threat to itself, whether real or perceived. This is especially true of nations that try to directly intervene in Cuba’s affairs, such as the U.S.. Conversely, the psychology of geographical isolation may have made Havana even more eager to agree to defense relationships with willing partners if the political conditions are favorable. Note that these two theoretical components are not mutually exclusive, and manifested themselves in the context of the Cold War between the US and Russia.

Trends towards Positive Change


While the release of Alan Gross is the single most striking (and coincidentally, the most actionable) of shifts towards more positive U.S.-Cuban relations, it is by no means the first. A number of events and trends have slowly moved the two nations towards that end. Since Raul Castro replaced his older brother in 2008, he has instituted several significant economic reforms including the relaxation of restrictions on small businesses, the decentralization of the nation’s agricultural sector by granting individuals and entities land leases, freeing up domestic real estate markets for public trade, and cutting the wall of red tape which effectively stifled public travel abroad. Additionally, Raul has also made consumer goods considerably more accessible to average citizens, including cell phones, and cellular and Internet service. And, while invisible economic forces in Cuba may eventually turn the nation towards better trade relations with the U.S., more immediately, the Wall Street Journal has reported that the U.S. private sector has been pressuring the Obama administration to grant access to the island’s markets, ostensibly to gain an edge over foreign competitors who have been denied access due to Cuba’s stringent control on the availability of consumer goods. These changes appear to be liberalizing Cuba’s domestic economic disposition, especially compared to the one that has dominated the island for decades. Although, as UCAL economist Richard Feinberg has stipulated, there is no absolute, direct causality between strides toward a free-market economic orientation and liberal political reform; theoretical and historical political trends suggest, however, a strong correlation between the economic barriers of a state and its political teleology. Therefore, while Cuba’s economic shifts over the last 6 years have been extraordinary, it may be to too soon to tell if these will translate into substantive political changes, especially given some of the limitations within these measures. Still, some foreign policy analysts consider these events to have provided fertile soil, and in the context of the agreement regarding Mr. Gross, the ideal opportunity for the U.S. to build relations with its island neighbor.

Of course, an even less extensive leap than economic reform to liberal political reform is that from political alignment to defense coordination. Along these lines, Cuba’s political and military alignment with the Soviet Union in the 1960s was born out of a fruitful economic arrangement. These ties led to strong political alignment by Castro, and were followed even more swiftly by a bilateral defense relationship.

Human Rights

Under Castro’s communist state, human rights in Cuba repressive at best. Since 1960 the government has not hesitated to imprison citizens who express dissent or dissatisfaction. The free press has been continuously silenced, and all forms of telecommunication are closely monitored, when not completely unavailable. Furthermore, until recently, foreign travel for Cubans was rarely allowed.

In 2010 and 2011, Human Rights Watch reported that Raul Castro released “dozens of political prisoners.” The government has also relaxed travel restrictions it once mercilessly imposed against its critics and their families. Furthermore, this relaxation expanded to include the Internet and cell phones (something that USAID had worked to achieve in the nation for nearly a decade). Increased freedoms brought by the Internet and cell phones also have significant implications for the future of human rights in Cuba. While overall conditions in country remain repressive, with phrases like “public acts of shaming . . . beating”, “termination of employment”, and “threats of long term imprisonment” associated with those who voice opinion that grapple with the status quo, it does represent progress of a kind.

Perhaps more so then the economic climate, the condition of human rights in a given state may be even more indicative of political ideology than its economic climate; these conditions predicated on many of the same foundational values and assumptions. By way of human rights, it is quite obvious that the current circumstances in Cuba are far from ideal, a point which some analysts use to limit hope for friendly long-term relations with the U.S. Nevertheless, the release of political prisoners demonstrates an incremental, limited progress.

The aforementioned reforms in economics and human rights, while seemingly insignificant to the free West, are indicative of massive changes within a nation that has been steadfastly repressive in virtually all aspects of civilian life for nearly 60 years. These nascent positive developments signal movement in a less repressive direction, and their aggregate effect over time may be something to which the free world can look forward.

Cuban Relations with Venezuela

While Venezuela is a federal presidential republic, the political leanings shared by the Bolivarian Republic’s two most recent leaders and the Castro brothers, plus its proximity to Cuba, make the two nations ideal allies and economic partners. Most of Venezuela’s major political parties are socialist. And, as seen during the spring 2014 protests in Caracas, the Maduro administration does not shy away from using violence against those who express dissent.

Since the beginning of the Chavez administration at the turn of the millennium, U.S.-Venezuelan relations have grown increasingly tense. Both Chavez and Maduro have publically declared opposition to the U.S. government. While both nations maintain embassies in the other’s capital, there has been no bilateral ambassador-level representation since 2010.

In 2000, Havana and Caracas made deals for the exchange of Venezuelan oil for Cuban healthcare training, equipment, and expertise. In 2004, Chavez and Castro resolved to combat U.S.-sponsored free trade, which they claimed would doom Latin America to poverty. To this end, they began a plan to integrate the economies of Latin American nations, beginning with their own.

Also beginning in 2004, the Cuban military helped Venezuela to bolster its own armed forces through its experience with Russian military equipment, as well the training of combat personnel. Cuba had mutual interest in providing assistance of this nature, as it viewed Venezuela as a valuable regional ally. Additionally, in 2011, foreign telecommunications firms installed the ALBA-1 undersea fiber-optic cable between the two nations, granting them direct communication, as well as increased Internet access and connectivity, especially in Cuba. On economic, political, military, and ideological grounds, the two nations seem to have forged an unalterable alliance.

In the near future, however, the two nations are bound to face political disagreements as tensions between the U.S. and Cuba have shown signs of cooling, The staunch anti-U.S. Maduro, who’s country also faces the prospect of U.S. sanctions seems to be left out. It seems likely that a pragmatic Raul Castro may favor economic cooperation with the U.S. over an increasingly irrelevant Venezuela.


The agreement to release Alan Gross may serve as a landmark and catalyst towards changes that could result in the eventual restoration of U.S. relations with Cuba. There are a few plausible courses of action that may have a positive result.

While poorly executed, a promising aspect of USAID’s attempt to leverage Cuba’s underground music scene for political instability is the notion that change in Cuba must be an entirely organic enterprise if it is to also be a successful and lasting one. The inception of voluntary political changes is likely the only way that the government will make changes significant enough to reverse the last half a century of turmoil. Access to information through the internet will be a major factor in this development.

While these freedoms appear to be increasing, it is possible that Havana is simply adorning the appearance of serious economic and human rights reforms in order to establish an economic life-line with the United States. Such a scheme, however, would be difficult to maintain in the long run. The more plausible alternative seems to be that Raul may in fact be serious about making reforms in these areas, even if only to improve Cuba’s economy. While less charismatic, Raul’s history indicates he is a much more pragmatic leader than his brother.

While basic U.S. principles seem to support the position that the US should qualify further developments with Cuba, such a course may rob current and future Cubans the opportunity to gain the freedoms which have the potential to lead to self-determination and a potentially democratic system in the future. By allowing the seeds of organic, grassroots change that have been sown through small economic and human rights changes, ideas and habits that habituate a people in autonomy and self-determination may embed itself in Cuban political and ideological identity for years to come. The U.S. has economic relations with other nations that have even more decrepit human right’s records. China is a state with which the U.S. government has continued to maintain strong economic relations. The PRC government has a terrible human rights record, and continues to be politically and social repressive towards its people. It is not economically advantageous or viable for the U.S. to cut ties with China just on principle. The gradual economic (and some minor political) liberalization by the PRC in local government over the past 10 years has begun to do this very thing; by granting local autonomy and freedoms for economic growth, irreversible notions and patterns of self-rule have been sewn among the Chinese people. By continuing to trade and keep open lines of communication and travel open despite the many differences between the two states has given the West a door into Chinese society that what simply not be possible if our policy mirrored the one we have towards Cuba.

These types of freedoms and grassroots political movements are difficult to retract and end once they have begun. Even if Raul Castro is merely showing the world the appearance of meaningful change for an infusion of U.S. capital, can he reverse the momentum resulting from freedoms and partial self-rule? The real issue before the free West is whether the Cuban people will be better off if we do open up dialogue and relations, even if the ruling government intends to take them back. Fortunately, even if Castro does decide to continue repressing the Cuban people after his objectives have been met, history suggests that once a populace begins hold certain freedoms, it is difficult to take them back.

If U.S. policymakers are keen on pushing Cuba full-throttle with ultimatums mandating overhauls in human rights and politics, then time might reveal that an event like the release of Alan Gross may have come too early. This may be the case if the U.S. moves to mandate improvements in political representation and human rights, and therefore not allowing the changes Raul has begun to turn in Cuba over the last 6 years to mature and take root. Hard pressure by the US regarding Cuba has not worked in the past and it is unlikely that it would now. While the U.S. should encourage and facilitate more liberalizing reforms like the few we have thus far observed, it may not be tactful for Washington to dictate what those should be, or to threaten consequences if the young nation did not meet a US-imposed deadline.

The best, most immediate logical next step to this end seems to be the encouragement of incremental, sustainable economic reforms, and – after the proper steps are taken to determine that the Cuban government should not belong on the list of state sponsors of terrorism – opening lines of communication with Washington. History supports the notion that the economic practices of a state and its political systems are intimately linked. Changes in one system influence changes in the other. From there, mid-term goals could include progress on human rights issues like continuing to free political prisoners, curb and eliminate violence and threats towards dissenters, and continue to allow the free-market to dictate travel and the use of telecommunications. Long term goals would be the manifestation of a free speech and press a protected by legislative measures.

Cuba is still young enough as a nation to break out of the ideological rut that has hampered its progress for the last half of a century. But if it is prompted by internal or external forces to dive back into its repressive practices, it may emerge much more difficult to rehabilitate than it is currently.

Whether the positive changes in economic policies and human rights are indicative of deeper, lasting changes remains unclear. For now, however, US policy makers should support open communication and economic partnerships wherever it can. If these are successful, over time, the United States may acquire a strategic military ally and trading partner.

OODA Analyst

OODA Analyst

OODA is comprised of a unique team of international experts capable of providing advanced intelligence and analysis, strategy and planning support, risk and threat management, training, decision support, crisis response, and security services to global corporations and governments.