Jason Reding Quiñones, the lead federal prosecutor in Southern Florida, recently put together a specialised team of lawyers and drug agents. The assignment for the group is to build criminal cases against the top rungs of the Cuban Communist Party in Havana, Cuba.
The initiative started as Donald Trump told reporters that Cuba would soon be forced to the bargaining table. The president had already invoked the International Emergency Economic Powers Act on 29 January, which cut off the flow of Venezuelan oil to the island and threatened tariffs for any other country attempting to supply Havana.
The administration is now dusting off the indictment machinery for a second act in the Caribbean following the offensive against the leadership in Caracas earlier in the year.
Cuba has navigated economic fragility for decades, as an American trade embargo has limited the access to foreign capital and left the infrastructure in a state of persistent decay. Even the healthcare system is currently fighting for life.
For years, Venezuela provided the oil Cuba needed through a subsidised swap for security and medical staff, but following the transition in Caracas, the oil flow has snapped. Now, Cubans are dealing with blackouts and a collapse in public transit.
The levers Washington is pulling are hitting home, and the administration is betting that the current level of deprivation will finally force a political surrender.
Cuba’s Resilience to the Venezuela Template
The administration portrays Cuba as the next target in the regional campaign. The two governments occupy very different positions, as Cuba lacks the kind of vast natural resource wealth that usually attracts foreign investment.
The Cuban military functions with a degree of ideological loyalty that prevents the types of internal fractures seen elsewhere.
Havana has survived everything from the Bay of Pigs to the post-Soviet collapse, and the researcher known as Boz noted in January that the Cuban leadership has a track record of remaining unified even as the country reaches a breaking point.
The island’s geography creates a strategic headache for Washington. Cuba serves as an outpost for foreign intelligence and military activity, and Christopher Hernandez-Roy from the Centre for Strategic and International Studies noted the goal is to remove rival powers from the region.
A destabilised Cuba risks entrenching a permanent foreign intelligence presence on the island, and the Soufan Centre reported that internal debates uncover a lack of the operational certainty seen in earlier manoeuvres.
The Iran War Stretches Washington Thin
The Cuba pressure unfolds as the U.S. enters the second week of war in Iran. Donald Trump started the airstrikes with Israel on 28 February, and since then, the conflict pushed oil prices to a punishing $90 a barrel.
The higher costs are making life expensive for voters and putting Republican support in jeopardy. A poll from CNN on 2 March recorded that nearly 60% of people are against the military action in Iran. The White House continues to search for a singular narrative for the conflict as the president watches a conflict he hoped would define a legacy turn into a global energy crisis.
Trump himself has admitted that Cuba remains a secondary concern until the Middle East campaign concludes. Robert Munks from Verisk Maplecroft noted that the campaign in the Gulf has temporarily taken the spotlight off Havana.
Par Kumaraswami, a professor at the University of Nottingham, noted that people in Cuba are getting more worried about surviving the global chaos. The delay might give Havana the breathing room it uses to wait out the short attention span in Washington.
Another Front in a Midterm Year?
The midterm elections in November were always set to be a referendum on the economic record of the administration. Right now, the White House meets the test from a position of historical vulnerability.
An NBC News poll from early March reported Democrats with a six-point lead, and most voters are unhappy with the current direction of foreign and domestic policy.
Another poll from NPR and PBS recorded that 61% of independent voters oppose the involvement in Iran, a group the president has struggled to hold since the 2024 election. Congressman Pete Aguilar complained that the administration is prioritising foreign wars over domestic healthcare and food programmes.
The Cuban leadership has proven uniquely capable of surviving generations of economic isolation. In Venezuela, sanctions displaced millions of people and the political core remained intact.
For thirty years, the United Nations has voted to condemn the U.S. approach to the island.
Washington is now attempting to replicate a specific regional victory against a country with a very different political DNA. The attempt to fight on too many fronts is often the first step toward a fall. A midterm electorate paying $90 a barrel for gas will likely recognise the overreach by the time November rolls around.
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