Since April 2019, the Trump Administration has imposed a series of increasingly strong economic sanctions against Cuba, effectively ending the previous policy of engagement begun by the Obama Administration in 2014 that had eased some sanctions and moved toward the normalization of relations. As a result, U.S. policy toward Cuba again is centered on economic pressure aimed at influencing the Cuban government's behavior with regard to not only Cuba's human rights record but also its support to the Venezuelan regime of Nicolás Maduro. Congress traditionally has played an important role in shaping U.S. policy toward Cuba through legislation and oversight, but it has appeared divided over Cuba the past decade, with some favoring engagement and others favoring strong sanctions.
In June 2017, President Trump issued a national security presidential memorandum on Cuba rolling back the Obama Administration's efforts to normalize relations and introducing new sanctions, including restrictions on transactions with companies controlled by the Cuban military and the elimination of people-to-people educational travel for individuals. To implement these changes, the Treasury and Commerce Departments amended, respectively, the Cuban Assets Control Regulations (31 C.F.R. Part 515) and the Export Administration Regulations (15 C.F.R. Parts 740 and 746) in November 2017. The amended regulations required people-to-people travel to be under the auspices of an organization specializing in such travel and prohibited financial transactions with entities controlled by the Cuban military, intelligence, or security services that appear on a State Department-maintained list. The State Department first issued its "restricted list" of Cuban entities in November 2017 and has updated it several times, most recently in April 2019. The current list includes 214 entities and subentities, including more than 100 hotels.
In 2019, the Administration has increased economic sanctions significantly:
On April 30, 2019, President Trump threatened a "full and complete embargo" on Cuba and "highest-level sanctions" unless Cuba ceased its military support for the Maduro regime. In a November 2018 speech, National Security Adviser Bolton asserted that Cuba was responsible for enabling the Venezuelan regime's repression. Bolton stated in numerous interviews that Cuba has some 20,000-25,000 security forces in Venezuela; regional experts say the figure is likely much smaller and that the Cubans there do not have combat capability. (Cuban officials assert that the vast majority of the roughly 20,000 Cuban personnel in Venezuela are medical workers.) In a May 5, 2019, television interview, Secretary Pompeo referred to a smaller number of 2,300 Cuban security personnel in Venezuela, maintaining they were providing security for Maduro; Pompeo also stated that "we're working with the Cubans" regarding the situation in Venezuela.
Critics of stronger sanctions on Cuba argue that such hardline measures will hurt the Cuban economy and people, including Cuba's emerging private sector, which has benefited from increased U.S. engagement, as well as current and future U.S. business interests in Cuba. They argue that stronger sanctions risk alienating U.S. allies who favor engagement. Supporters of stronger sanctions assert that only sustained economic pressure will influence the behavior of the Cuban government and foreign companies thinking about investing in confiscated property in Cuba. They also view Cuban support as a major factor helping prolong Venezuela's political crisis.