Introduction

Economic sanctions have been used as coercive instruments by major international actors for centuries, both during armed conflicts and in peace time. The latter part of the twentieth century registered an increased usage of targeted or smart sanctions. These existed in earlier times,Footnote ¹ but they came to the forefront in the post-Cold War world.Footnote ² Among the most prominent are the asset freezes and other financial sanctions imposed on individuals and entities, sometimes known as “blacklists.”

These listings are often publicly presented as carefully crafted, precise, and humane instruments. They are supposedly oriented toward specific individuals and companies, rather than entire countries. However, there have been debates about their efficacy, their ethical nature, and their actual capacity to avoid or reduce harm for common people. Cuba is one of the targets of these sanctions and an important case study for a better understanding of this instrument in real conditions.

Economic sanctions against the country are in all cases unilateral policies imposed by the US. Neither the UNSC nor any other international organization has sanctioned Cuba. The sole exception, a political sanction, was Cuba’s expulsion from the Organization of American States in January 1962, which was lifted in 2009. These measures have been a key component of US policy towards the island since 1959, as part of a state policy aimed at bringing about regime change and restoring US influence. Prior to the 1990s, American policymakers prioritized comprehensive sanctions, called an “embargo” in the US and “blockade” in Cuba,Footnote ³ that form a multilayered complex system with an intricate legal structure. In the 1990s, the sanctions were expanded significantly through legislation and regulations. The relatively recent expansion of the role of blacklisting adds a layer to the system.

The legitimacy of the US sanctions against Cuba has long been challenged, not only by Cuba and its allies but also by the international community. Since 1992, the UNGA has overwhelmingly adopted resolutions condemning the US measures against Cuba for violating international law, particularly the aspects that are extraterritorial. The most recent vote in the moment of writing these lines, the thirty-second, in October 2024, was 187 votes in favor, with 2 against (US and Israel), and 1 abstention (Moldova).Footnote ⁴ The legality of such measures has been challenged by the UN Special Rapporteur on UCMs as well as other legal scholars.Footnote ⁵ The sanctions have been widely criticized by Amnesty International, the American Association of World Health, and many other organizations.

There are good reasons for these criticisms. The US justifications for its unilateral measures have become increasingly tenuous. From 1959 to1989, sanctions against Cuba were justified mainly on the basis of the threat of Communism. With the end of the Cold War, the discourse shifted towards secondary arguments: Cuba’s alleged support for terrorism, and violations of human rights. The US includes Cuba on its unilateral list of “States Sponsors of Terrorism” for its support of revolutionary groups decades ago.Footnote ⁶ The accusation of human rights violations has appeared constantly in speeches and in the preamble of sanctions legislation since the 1990s, implemented with devastating effect on the country, even though violations recorded by Human Rights Watch in Cuba are minor when compared to those registered in countries such as Saudi Arabia and Colombia, both of which have been traditional Washington allies.Footnote ⁷ Indeed, Amnesty International and others have criticized the sanctions themselves as constituting human rights violations.Footnote ⁸

Nonetheless, the US enforcement of its sanctions against Cuba has continued, largely unabated, and its use of individual listings against Cuban nationals, and against third parties engaged in trade with Cuba, have grown considerably. Much of the blacklisting against Cuban nationals and Cuba-related entities has taken place through the OFAC’s SDNs and Blocked Persons List. It includes natural persons; ships; SDNs; specially designated terrorists; specially designated global terrorists; foreign terrorist organizations and specially designated drug dealers. It includes listings in which all properties and interests of the sanctioned person are blocked, and in which all kinds of transactions with US nationals are forbidden; and third-country parties that deal with those listed can be fined or blacklisted.Footnote ⁹

In gathering data on all those who have been blacklisted by the U.S. Department of the Treasury and the U.S. Department of State, our primary source was the U.S. Federal Register, unless otherwise indicated. The Federal Register serves as the common source, as all modifications to the lists are published there. We verified its reliability by randomly comparing its records to the lists published by OFAC. Aggregate data presented below is a composite of information taken from all lists that include Cuba-related designations. We also used other sources, including materials from the Treasury Department’s OFAC, Cuba’s National Office of Statistics and Information (Oficina Nacional de Estadísticas e Información, ONEI), and the US Congress’ digital archives.

We reviewed all listings related to Cuba from 1994–2021. This time frame encompasses the presidencies from Clinton through the first year of the Biden administration. This period also covers critical events in Cuba, most significantly the crisis of the 1990s and the economic and political reforms that followed. In that period, 961 Cuba-related designations were listed. We categorized the listings as four types: 61.4 percent were entities in Cuba; 23.3 percent were entities outside Cuba; 9.7 percent were natural persons; and 5.6 percent were vessels.

In the following pages, we explore the history of the listings as part of the US’s Cuba policy within that time frame. We explore their scope and their objectives, and we question whether they are in fact “targeted.” This discussion will contribute to a more complete view of a tool increasingly used by the United States in the twenty first century.Footnote ¹⁰

The Rise of the Blacklists: From Bill Clinton to George W. Bush

The 1990s were an extraordinarily difficult period for Cuba. The collapse of the European socialist bloc and the dissolution of the USSR meant the loss of an estimated 85 percent of demand for Cuba’s exports and 70 percent of its imports, and its main sources of credits and technology, as well as the loss of its most important political allies.Footnote ¹¹ This caused a deep crisis and triggered a series of reforms and the search for new markets and business partners.

At the same time, the US was in the position to reconsider its policies in the context of the post-Cold War. In the cases of China and Viet Nam, Washington opted for lifting economic sanctions and normalizing relations. However, the US’s Cuba policy went in the opposite direction. In 1992, Congress passed the Torricelli Act, which codified the sanctions regulations into statutory law,Footnote ¹² removing the president’s discretion to modify or terminate many of the provisions of the sanctions regime. In 1996 Congress passed the Helms–Burton Act,Footnote ¹³ which furthered these efforts. Both of these statutes went well beyond bilateral effects, and intervened extensively in Cuba’s trade with third countries, at the time when establishing new trade relations was critical to Cuba’s ability to address its economic crisis. In addition, these statutes targeted several key sectors of the Cuban economy: shipping; exports of raw materials, including sugar and nickel, Cuba’s leading exports at the time; the rapidly growing sector of biotechnology and medical exports; and foreign investment. These are discussed in Raúl Rodríguez Rodríguez’s chapter in this volume.

The making of that iteration of US’s Cuba policy was shaped by several factors. Neoconservative and other conservative groups with hardline stances in international affairs were increasingly influential both in the 1980s and in the aftermath of the Cold War. The anti-Castro Cuban–American community in Florida was a vocal player in the post-Cold War Cuba policy and the broader policy towards Latin America. In the geopolitical context, unlike China and Viet Nam, Cuba is located in the immediate surroundings of the United States, in an area critical as the pivot of US power in the Americas. In the early 1990s, there was a clear perception of Cuba’s weakness and a subsequent estimation that the Cuban political regime had little likelihood of surviving. Thus, there was a perception that Cuba’s economic crisis presented an opportunity to bring about the end of the Cuban post-revolutionary government.Footnote ¹⁴

The Cuban–American community in Florida heavily influenced each presidential administration, as well as the campaign platforms of presidential candidates. Florida was the largest swing state, where a few thousand votes could decide a presidential election. Indeed, George W. Bush took office in January 2001 after a highly contested and controversial election, decided by 537 votes in Florida and a ruling by the US Supreme Court. The evidence shows that the alliance between the Republican Party and the Cuban–American political elite was a major factor in Florida’s shift from solidly Democratic to a swing state, and in Bush carrying its electoral votes in 2000.Footnote ¹⁵

Meanwhile, Cuban–American representation in Congress grew steadily, with Cuban–Americans gaining positions of influence in both the House and the Senate – for example, Ileana Ros-Lehtinen, former Chair of the House Committee on International Relations, and more recently Marco Rubio, who alternated as chair and ranking member of the Senate Committee on Foreign Relations. Political processes within Florida were heavily influenced by the “Cuban-American political machine,”Footnote ¹⁶ which included a number of hardline “anti-Castro” organizations that consequently gained significant political clout at local, state, and federal levels.

But counter to the expectations of these political actors, the Cuban government did not collapse. It coped with domestic political issues and managed the social and migration crisis of 1994. By 1995, the economy of the island had begun to recover, as the country was slowly rerouting its international trade, opening up to foreign investment, adjusting its management structures, and reorganizing its core sectors.Footnote ¹⁷

In their respective efforts to secure Florida’s electoral votes, George H.W. Bush and Bill Clinton signed into law two major pieces of legislation reinforcing the blockade. Bush signed the Torricelli Act in 1992, and Clinton signed the Helms-Burton Act in 1996. Both did so a few months before their respective general elections.

The following year, the Clinton administration expanded the reach of the sanctions regime considerably through the use of blacklists. In 1997, the administration blacklisted hundreds of Cuba-related persons and entities. These were predominantly (about 85%) vessels and Cuba-owned or Cuba-related companies and offices abroad. The significance of these designations is clear: Cuba’s international trade activities were critical to the retooling of its economy and its new economic relations. Thus, the listings of 1997 functioned as a supplement to the Torricelli and Helms–Burton laws, reinforcing their measures targeting Cuba’s access to shipping, access to new markets for its exports, and access to new international suppliers.

Forty-five vessels were blacklisted in 1997. Four of them were owned by Cuba or had the Cuban flag, and the rest were vessels that had shipped goods to or from Cuba and were owned by foreign parties and sailed under foreign flags. All of these listings came on top of a provision of the Torricelli Act banning any vessel that had docked in Cuba from docking in US ports for 180 days.Footnote ¹⁸ These actions, in combination, sought to undermine Cuba’s access to international maritime trade.

Also in 1997, the Clinton administration dramatically expanded the blacklists concerning Cuba-related entities abroad, adding 195 such entities. By contrast, no such entities were listed in 1996, and only one was listed in 1995. The composition of these listings is also significant: 88.6 percent were classified as commercial, storage and transportation companies and offices.

The sensitivity and complementarity of these two categories are apparent. On the one hand, as an island nation, Cuba’s international trade is dependent on maritime shipping. On the other, commercial offices, shipping companies, foreign commercial companies, and storage facilities are all major components of any country’s foreign commerce. By targeting them, the US was effectively targeting the entirety of Cuba’s international trade in goods. Cuba’s trade is not only a source of revenue, but an indispensable supply line for basic consumption goods for the general population, as well as for capital goods for the operation of the economy at large.

In 1997, the administration also blacklisted sixteen natural persons (Figure 9.1) and twenty-six entities in Cuba (Figure 9.2). Among the natural persons were the representatives of Banco Nacional de Cuba (Cuba’s Central Bank at the time) in Spain, Japan, and Switzerland,Footnote ¹⁹ which affected the bank’s operations abroad, as the signatures of the bank’s representatives were needed to authorize documents for a wide variety of financial transactions and other operations.

Figure 9.1 Natural persons by year of inclusion, 1994–2021.

Source: Elaborated by the authors with data from the Federal Register.

Figure 9.2 Sanctioned Cuban entities by year of inclusion.

Source: Elaborated by the authors with data from the Federal Register.

In 1997, the targeted entities within Cuba were all economic units. All designations referred to state-owned enterprises (SOEs).Footnote ²⁰ Most of them were shipping companies, which again meant additional restrictions for overall exports and imports. Hence, these two categories – natural persons and entities within Cuba – complemented the listings of ships and Cuban entities abroad, all of these undermining Cuba’s efforts to establish new trading partners and sustain its imports, exports, and international financial transactions.

Whatever rationale was used, revenue generated by state-owned companies in Cuba is a direct contribution to the government’s budget and thus is a source of funding for healthcare, education, and social assistance – the main areas of public spending, typically around 60 percent of Cuba’s budget.Footnote ²¹ When the state’s revenues are compromised, this affects the country’s ability to secure food, oil, medicines, and other essential supplies. Hence, measures significantly impacting state revenues would inevitably impact the well-being of the general population. This, along with the targeting of foreign trade, meant that this early surge of listings broadly targeted both the state and the economy, expanding what was already a complex and extensive array of existing sanctions. Importantly, these came in the early stages of Cuba’s recovery after a deep economic crisis, thus hampering its development.

After 1997, the number and frequency of Cuba-related listings declined significantly for several years. While the George W. Bush administration adopted various measures which were adverse to Cuba, these did not include extensive blacklisting during his first term. Rather, the administration adopted a different set of initiatives to undermine Cuba’s economy. The Bush administration made it extremely difficult for Cuban entities and persons to use US dollars by imposing multimillion dollar fines on foreign institutions that offered financial and banking services to Cuban persons and entities, starting with the Swiss bank UBS.Footnote ²² This made it very difficult for Cuba to conduct regular international financial operations, settlements, and deposits. Also, remittances sent by Cuban–Americans to their family members on the island – a major source of revenue to the country that went directly to regular Cubans – were restricted in regard to the amount that could be sent, how frequently remittances could be sent, and the legally permitted recipients.Footnote ²³ The Bush administration also created programs, structures, and offices officially designated to drive regime change in the Caribbean country, such as the Commission for Assistance to a Free Cuba.Footnote ²⁴

In spite of the obstacles, by 2006, the Cuban economy had recovered to a significant degree. Its GDP grew by double digits in 2005 (11.2%) and 2006 (12.1%).Footnote ²⁵ This improvement was met with a new round of targeted sanctions.

In 2007, seventy-nine new Cuba-related designations were included in OFAC’s blacklist in all categories. Forty-six natural persons were listed (Figure 9.1), the majority related to the economy: managers in state-owned companies, economy-related government officials, and foreign investors and owners of foreign companies doing businesses with Cuba.Footnote ²⁶ These included, for example, Julio Imperatori,Footnote ²⁷ at that time the Managing Director of the Havana International Bank, and Guadalupe Ortiz,Footnote ²⁸ representative of Cubanatur, then a Cuban travel agency in Mexico, D.F.

Also in 2007, four vessels and twenty-nine entities were blacklisted. The latter included twenty-two entities outside of Cuba, such as Hola Sun Holidays Limited, a Canadian travel agency specializing in Cuba travel, and seven entities within Cuba, including Cimex, one of Cuba’s largest import–export corporations.Footnote ²⁹ The pattern here suggests the targeting of two major sectors of the Cuban economy: international tourism and, once more, international commerce. It is worth noting that Canada had for decades been the biggest market for Cuba’s tourism industry; hence blacklisting a specialized Canadian travel agency had the potential to directly cause some disruption in the Cuban economy, while serving as a warning to other such agencies to terminate their business with Cuba or face legal and financial consequences.

When government officials or executives in state-owned companies are listed, their ability to perform their work, such as trade or investment negotiations, is undermined, as foreign companies will be wary of transacting business with them, for fear of running afoul of US law. Foreign investors, and foreign companies doing business with Cuba, face similar risks, and would have reasons to withdraw from the Cuban market. These tendencies would cause particular harm in an economy that is mostly state-owned and state-managed, with a limited pool of potential business partners. It is similarly important to note that in many of these cases, sanctions against companies and individuals were not justified by claims that they had engaged or were engaging in unlawful practices against American citizens, the American government, or international law; rather, these were framed as sanctions against the Cuban government.

While the US administration justified these listings by reference to various claims of human rights violations and putative ties to terrorism by the Cuban government, it is clear that, substantively, these listings functioned as measures targeting critical state functions, as well as Cuba’s trade relations and foreign investors.

Back and Forth: From Obama to Biden

The election of Barack Obama in 2008 signaled a new stage in US foreign policy. The international system was drifting away from the unipolar model assumed by the previous administration’s foreign policy, and there had been major political changes in Latin America. An adjustment of US foreign policy was necessary.

In that context, the Obama administration, particularly during its second term, took several steps toward improving relations with Cuba, most notably the restoration of diplomatic relations in 2014, which were severed by the US in 1961; the lifting or softening of some sanctions; and the opening of a series of official negotiations aimed at normalizing bilateral relations. The administration removed 231 Cuba-related designations from the blacklists: 45 vessels, 99 entities abroad, 26 entities in Cuba, and 61 natural persons (Figure 9.3). In 2015, Cuba was removed from the list of State Sponsors of Terrorism.Footnote ³⁰ All of this sent positive signals about the future of US–Cuban relations. This is the only administration in the period addressed in this chapter to reduce the number of designations, and did so by a large margin, with a net of 225 removals.

Figure 9.3 Persons, entities, and vessels removed from the lists, 1994–2021.

Source: Elaborated by the authors with data from the Federal Register.

However, the core of the sanctions regime – the statutes from the 1960s and 1990s – remained in place. Also, a number of the designations that were removed concerned companies that had gone out of business, and deceased individuals, so the delistings were less significant than the numbers would suggest.

The Obama administration did however use listings to create additional pressure on the Cuban state and economy,Footnote ³¹ although at a lower level than Obama’s predecessors and with a twist. The administration added five new designations in the category of natural persons. The last three of them, introduced in 2016, were different from prior ones, as they were groups rather than individuals: members of the Council of Ministers, flag officers of the Revolutionary Armed Forces, and members of the Politburo (Political Bureau of the Communist Party, in its official nomenclature).Footnote ³²

While it may seem on the surface that these listings were minimal and highly targeted at influential government officials, in reality, these three designations directly affected a much larger number of persons than any of the previous listings. Particularly, they include any minister in charge of economic affairs, whoever that person is, regardless of their personal history, without any allegation of personal wrongdoing. What this means is that anyone in those positions will be excluded from any potential negotiation with US counterparts, and their participation in agreements with third country-based companies could be used against the foreign party. This essentially forces structural and operational changes, such as the designation of lower-level officials to carry tasks previously attached to the ministerial office and adds another layer to the decision and supervision process, as those functions will still be under the competence of those ministries and their ministers.

In addition, there was a large increase in the size of the penalties imposed, particularly on banks, for sanctions violations, including transacting business with those who were blacklisted. In several cases, the administration bundled up multiple violations of the regulations in cases against major foreign banks: the Dutch bank ING, the British bank HSBC, and the French banks BNP Paribas and Crédit Agricole. These banks were penalized on the basis of their operations with several sanctioned countries, including Cuba, with penalties in the hundreds of millions or even in the billions of dollars, along with the threat of suspension of their licenses to operate within the US financial system (Table 9.1).

In 2009, OFAC then published a set of enforcement guidelines; in combination with the new maximum for civil penalties, the result was a dramatic increase in fines. Between 2009 and 2014, “mega-fines” were introduced; the largest penalties increased by an astonishing 48,000 percent, from $2 million to $963,619,900.Footnote ³³ The total annual penalties likewise skyrocketed, increasing 27,700 percent from $4,344,686 to $1,209,298,807.Footnote ³⁴ But even without the “mega-fines,” the average fines more than doubled after the changes.Footnote ³⁵

These penalties significantly increased the risk for foreign companies doing business with Cuba and sent a chill throughout the global banking community. This in turn created impediments and additional costs for Cuba’s transnational transactions in general, broadly affecting its imports, exports, and foreign investment.

It would seem that US sanction practice under the Obama administration, specifically in regard to Cuba, was contradictory. On one hand, there were not a great many additional listings under this administration, or at least so it appeared; and the administration granted new licenses to US companies to do business in Cuba. On the other, extraterritorial enforcement against international “violators” of the unilateral sanctions was so severe that it sent shock waves throughout the international business community, particularly the banking industry.

However, this policy was in fact quite coherent and corresponded to Obama’s general approach to foreign policy. Changes in the listings did not represent a significant reduction in their use, but rather their transformation into a tool that gave the US government increased latitude in the interpretation and enforcement. This allowed their application in a more adaptive fashion, so that they could be adjusted to the circumstances. That is, they fit neatly within the framework of the “smart power” approach.Footnote ³⁶

Thus, under the Obama administration, while the listings may have been explained by reference to human rights violations and so forth, they functioned very specifically to weaken Cuban political and social institutions. The application of the sanctions also had the effect of undermining Cuba’s ability to engage in global commerce, by compelling the withdrawal of international banks, such as Banque Nacionale de Paris (BNP Paribas) and Spain’s Banco Sabadell S.A., which occurred in 2013.Footnote ³⁷ As non-American companies were deterred from doing business in Cuba, this allowed American companies to benefit from the license system under the policy changes that were taking place in parallel.

Around the same time that OFAC began imposing large-scale penalties against European companies for engaging with Cuba, the Obama administration started to issue licenses for American companies of different types and sizes interested in doing business in Cuba. For example, in 2015, Florida’s Stonegate Bank secured a license and became the first US corresponding bank for Cuban counterparts.Footnote ³⁸ Also in 2015, Sprint reached an agreement with Cuba’s state-owned telecommunications company ETECSA to offer joint roaming services;Footnote ³⁹ and in 2016, Sheraton began operating a hotel in Havana, as its parent company at the time, Starwood Hotels, negotiated with Cuba’s Habaguanex S.A. for management contracts for other hotels in the city.Footnote ⁴⁰

Thus, the listings, and the huge penalties, undermined Cuba’s trade with third countries, while the expansion of licenses gave US companies an entry point into the Cuban market. However, this development came to a halt and was then reversed under the next administration, thus negating any potential long-term benefit for American companies, while keeping the pressure on third-country based companies.

The Trump administration, which included figures such as Mauricio Claver-Carone and John Bolton, had close ties with the conservative elites within the Cuban–American community, and legislators such as Marco Rubio, Mario Díaz-Balart, and Maria Elvira Salazar, as well as Florida-based Political Action Committees and lobby groups controlled by Cuban–Americans, were important assets for Trump in Congress.Footnote ⁴¹ The new administration ordered a review of the Cuba policy, and starting in June 2017 engaged in increased pressure as well as renewed calls for regime change, thus shifting away from the more nuanced approach espoused by the Obama administration.Footnote ⁴²

In 2017, the Trump administration modified the listings of natural persons added by Obama. The modification eliminated one of the designations (members of the Politburo), replaced the other two with much broader versions, and added ten totally new designations, in order to include in the lists:

These were in addition to other broad listings, such as members and employees of the National Assembly of People’s Power (Cuban Parliament), members of any Provincial Assembly of People’s Power (provincial parliaments), and local sector chiefs of the Committees for the Defense of the Revolution (the largest mass civil organization in the country).

Once again, these were not lists of individuals by name, but rather these were labels denoting groups of variable size and composition. Many of them were not state officials, such as the employees of the ministries or the Supreme Court. This category, for example, encompassed janitors, human resources office workers, receptionists, and other personnel employed by those institutions. These sanctions also meant that these persons could not legally receive gift parcels and communications devices sold by US nationals.Footnote ⁴⁴ In addition, they could not receive remittances from anyone in the United States or sent through American intermediaries.

The collective listing of categories of natural persons effectively targeted much larger numbers of individuals than prior designations. Any of the institutions mentioned employs hundreds or thousands of persons, many of whom are not officials. Also, the vagueness of the language allows for broad interpretation, thus threatening even larger numbers. Thus, the nature of the designations makes even clearer the intention of hurting the state as a whole, rather than specific “wrongdoers.”

This also created risk and uncertainty for those in Cuba involved in government: because the new listings incorporated broadly worded categories whose scope was uncertain, individuals in many cases could not be certain whether they had been designated or not. This also translated as uncertainty for companies doing business with Cuba, since they could not be entirely certain whether a specific government official was or was not covered by the vaguely worded categories. The uncertainty, combined with the severity of the penalties OFAC was imposing, contributed to an adverse risk assessment, and consequently in many cases the withdrawal of foreign companies from the Cuban market.

After the 2018 midterm election, the Trump administration scaled up both its rhetoric and its actions against Cuba. This appeared to respond to three major factors. First, the Cuban economy was slowing down, and opposition groups within and outside Cuba were increasingly active, responding to a perception of weakness of the Cuban government. Second, Florida had shown itself to be an important electoral stronghold for the president. Third, there emerged a camp of political rivals, self-described as socialists, notably Bernie Sanders; associating them with the “horrors” of countries like Cuba and Venezuela could pay off on the campaign trail.Footnote ⁴⁵

The Trump administration took several steps that substantially increased the economic impact of US sanctions. In 2019, the administration began to implement Title III of the Helms–Burton Act – a controversial provision that authorized lawsuits, in US courts, against foreign companies doing business in Cuba involving certain properties – which had been suspended by US administrations since the inception of the law in 1996, due to its extraterritorial nature and the fear of alienating allies. Also, in January 2021, shortly before Biden’s inauguration, Cuba was added once again to the list of State Sponsors of Terrorism.Footnote ⁴⁶

In addition to these measures related to legislation and policy, the Trump administration substantially expanded the use of blacklists, starting early in the administration and increasing the listings in the run-up to the presidential election. These listings were used in a manner that was different from the approach of the Obama administration. The Trump administration policy was unequivocally geared toward maximizing the economic pressure on Cuba, while explicitly calling for regime change. But the administration also utilized the blacklists as a domestic political strategy in a manner that had not occurred before.

One of the significant expansions of the listings took place in 2017, when the administration created the List of Restricted Entities and Subentities Associated with Cuba (Cuba Restricted List). The Treasury Department framed the list as targeting “Cuban military, intelligence, or security services or personnel with which direct financial transactions would disproportionately benefit such services or personnel at the expense of the Cuban people or private enterprise.”Footnote ⁴⁷ However, most of the entities listed are related to the civilian economy, including dozens of hotels across the country, beverage manufacturers, agricultural enterprises, and stores selling consumer goods.

The Trump administration, through the combined use of this and the other lists, added more designations than the Clinton, Bush, and Obama administrations combined – a total of 550. The bulk of these were added in the first year of the administration and in its last year, with the largest number added in the run-up to the presidential election (Figure 9.2). Of these, 544 were state-owned enterprises, state-owned holdings, and other smaller economic units.Footnote ⁴⁸ In the context of the Cuban economy as a whole, the sheer scope of these listings is enormous.

According to Cuba’s ONEI, as of 2020 there were 1795 state-owned enterprises of all types in the country.Footnote ⁴⁹ The state sector, consisting of companies and public institutions, was and is the predominant economic sector. As of 2020, there were no private Cuban companies, and the private sector consisted only of self-employees and family businesses. Thus, listing hundreds of SOEs and other state-owned economic units had a direct large-scale impact on the economy as a whole. Part of the listed entities were military industries, but the majority were civilian SOEs and other economic units.

Entire sectors were profoundly affected. For example, of Cuba’s seven hospitality chains, the five largest ones are blacklisted. Cubanacan had been listed since 2007,Footnote ⁵⁰ but the Trump administration added Habaguanex in 2017,Footnote ⁵¹ and Gaviota in 2020.Footnote ⁵² In September 2020, the Trump administration announced the establishment of the Cuba Prohibited Accommodations List. It prohibits persons subject to US jurisdiction from staying at any of the listed hotels, hostels, rental houses, and other accommodations.Footnote ⁵³ This added nearly 300 designations and an extra layer of difficulty for any US person who visits the island, as finding a permissible accommodation becomes more complicated.

Also in September, AIS Remesas, a Cuban state-owned company that processed remittances sent from abroad, was blacklisted.Footnote ⁵⁴ On October 26, 2020, the administration announced the listing of Fincimex, another Cuban company that serves as a hub to receive remittances.Footnote ⁵⁵ The listing of Fincimex and AIS had a significant impact on the economy at large. These were the counterparts of Western Union in Cuba, and they channeled between $900 million and $1.5 billion per year – equivalent to up to 1.5 percent of the country’s GDP prior to the pandemic – that went to common citizens to support household consumption or the establishment of then emerging private businesses.Footnote ⁵⁶ The actual volume of remittances is unknown, as important amounts are moved through irregular means, mostly carried in person by Cuban–Americans visiting the island. However, the blacklisting of Fincimex and AIS was particularly disruptive, since it forced the suspension of regular financial flows in the midst of the Covid-19 pandemic, when international travel was paralyzed; thus, their listings, along with the border closings due to the pandemic, effectively blocked almost all remittances to Cuba.

The Trump administration removed some designations from the lists, albeit in much smaller numbers – a total of only six (Figure 9.3). In addition, three of those removals were in fact part of the expansion of collective designations of natural persons, hence these are technical removals, not proper delistings. In total, Trump added a net 557 Cuba-related designations and established two additional Cuba-specific lists.

While the blacklists have always been closely tied to foreign policy and domestic politics, the Trump administration politicized them even more, by openly incorporating them into the rhetoric of the electoral process. As mentioned previously, some of the most visible listings occurred in the months and weeks leading to the presidential election of 2020. Also, sanctions can be announced in part or in advance and then again when implemented, to maximize their political effect, both in Cuba and within the US. For example, while the Fincimex listing was not actually implemented until December 2020,Footnote ⁵⁷ it was announced shortly before the election, in October 2020. In the case of Trump, this was clearly intended to cater to the anti-Cuban government Cuban–American political organizations and constituents in the important state of Florida.

And while the ostensible objective of the listings was to target individuals in the government or military who were engaged in wrongdoing, in fact the Trump administration listings were directed at hundreds of state entities and major sectors of the economy, such as tourism, remittances, and access to international banks. In the face of these restrictions – and the actual or perceived risk of doing business with Cuba – hundreds of banks and companies from third countries declined, withdrew, or severed trade relations, impacting employment, public services, and the financial stability of large swaths of the Cuban population.

When Biden assumed the presidency in January 2021, there were expectations of a change in Washington’s Cuba policy. However, all previously existing sanctions were kept in place. The Biden administration, as of this writing, had in substance, if not in rhetoric, remained more in line with Trump’s policy of maximum pressure than with Obama’s more nuanced and flexible approach, albeit without the flurry of new listings and other sanctions measures introduced by Biden’s predecessor.

After incidents involving social unrest in Cuba in the summer of 2021, the administration listed four additional entities, all of them law enforcement agencies and military bodies that belonged to already designated institutions or were formed by personnel already included in collective designations. The administration also added ten individuals, mostly high-ranking military officers. In the same year, two vessels were added to OFAC’s list. In parallel, it delisted one vessel. Hence, by the end of 2021, the Biden administration had added a net fifteen designations.

These listings were mostly political in nature,Footnote ⁵⁸ except for the vessels, and were oriented toward political messaging more than at directly affecting those individuals and entities. However, these listings signaled that the return to engagement policies, closer to Obama’s approach, was unlikely.

Conclusions

While asset freezes and other forms of blacklisting were touted in the early 2000s as the ideal form of targeted sanctions, in regard to the US measures against Cuba, we see that that is not the case. It may well be said that the listings are “targeted,” but not in the sense that they are limited to individual actors engaged in human rights violations or support of terrorism. What can be said is that in crucial aspects they are in fact targeting major sectors of the Cuban economy, specifically imports, exports, investment, and transnational financial transactions, including family remittances.

While the stated justification for the sanctions concerns human rights and terrorism, the nature and the timing of the listings suggest policy objectives that are largely unrelated. The listings were notably increased, or their impact was expanded in some other way, at times of particular vulnerability for Cuba, or to undermine a trajectory of positive growth, or in conjunction with US domestic political agendas and election cycles, or as a means of excluding foreign business in Cuba while giving US companies access to the Cuban market. What becomes apparent is that the listings to a great extent function not as a process concerned with individuals, but rather as a set of policy tools that complement the statutory measures, and correspondingly are aimed at compromising large sectors of the Cuban economy, appeasing an influential US domestic constituency, or seeking to achieve regime change.

In 1997, there were significant increases in listings of vessels as well as Cuban entities operating abroad; the first affected Cuba’s access to maritime shipping and the second concerned its efforts to expand trade relations. Both of these were critical to Cuba’s economic recovery in the 1990s. The 1997 measures came on the heels of the Helms–Burton Act, reinforcing and complementing the explicit sectoral measures found in the statute which targeted shipping, exports, and imports.

From 1998 to 2006, there were not significant large additions to the blacklists. However, there were other measures with broad economic impact that were in place, such as prohibitions on transactions involving US dollars, and restrictions on remittances. The former created significant impediments to Cuba’s foreign trade, and the latter undermined a major source of hard currency flows into the country.

Despite these obstacles, 2005 and 2006 saw significant growth in Cuba’s GDP. In 2007 – in response, it seems, to Cuba’s economic growth – there were seventy-nine new listings, many of which were related to the economy: managers in state-owned companies, economy-related government officials, foreign investors, and owners of foreign companies doing businesses with Cuba.

The Obama administration removed over 200 listings and removed Cuba from the State Sponsors of Terrorism list. This administration added new listings, but they seemed minimal – barely over a dozen. However, the listings were largely framed as categories of persons, rather than lists of named individuals. Given the breadth and vagueness of these categories, alongside drastic increases in the monetary penalties on banks and others doing business in Cuba, the risk assessment of these actors was heightened, and many withdrew from the Cuban market altogether. At the same time that foreign companies with ties to Cuba saw their risks increasing dramatically, US companies were receiving far more licenses to do business in Cuba, suggesting that the listings were motivated less by human rights concerns than by an interest in preserving the Cuban market for US companies.

The Trump administration not only rolled back many of Obama’s initiatives with Cuba, but also blacklisted hundreds more Cuban entities. The specific listings included major actors in the tourism industry and in the transfer of remittances, both of which are critical sectors of the Cuban economy. Also, the Trump administration expanded Obama’s collective designations, sometimes with unclear parameters and ambiguous wording. This created uncertainty on the part of the Cubans who might or might not have been the intended targets; and created uncertainty as well on the part of foreign businesses that would be wary of engaging with government officials who even might be considered listed persons in the eyes of the US.

This administration also introduced a degree of overt politicization that was notable: in the run up to the 2020 presidential elections, the Trump administration announced new listings of major economic players, such as Fincimex, and other measures, such as the establishment of a new list further targeting tourist lodging. While administrations since Clinton had used the sanctions policies to court favor with the Cuban–American community in Florida, Trump not only did this at the level of policy, but also explicitly incorporated the listings in the rhetoric (and the timeline) of the presidential electoral campaign.

The differences among administrations indicate that blacklisting, sanctions at large, and the Cuba policy in general were deeply intertwined with the evolution of US policies and politics, both domestic and international. Far from being “smart” sanctions, the listings impact entire sectors, and create multiple new barriers for an already sanctioned economy. By targeting the state-owned sector primarily, the listings directly affect the foundation of the entire economy and the organizations that employ the vast majority of the labor force. They limit the development of private initiative by reducing the flow of remittances, cutting investment and supplies, and shrinking the customer base. In these ways and in others, the listings drastically reduce the ability of the entire population to access basic services and obtain needed consumer goods, and they worsen the hardship and poverty.