The blackouts keep coming in Havana. For years, the Soviet-era power grid has slowly collapsed under the weight of what Secretary of State Marco Rubio calls an “incompetent communist” regime. The Trump administration has upped the ante with escalating economic, diplomatic, and legal moves that target the regime while offering significant support for the Cuban people. If President Donald Trump and Secretary Rubio keep the pressure on, the Castro family’s luck might finally run out.

The ongoing collapse of Cuba began long before the Trump administration turned its attention to the island. When President Barack Obama traveled to Havana and linked arms with Raúl Castro in 2016, he expressed hope that his decision to normalize relations with the communist regime would bring “generational change.” Castro, who is now a fugitive from U.S. justice, humored Obama, and then used the opening to line the pockets of party elites, not create better lives for Cubans.

Between 2015 and 2020, state investments tied to tourism, including new hotels and resorts, increased to nearly 50% of total investment on the island, more than five times the spending on the power grid and water supply. Most of those investments went through Grupo de Administración Empresarial S.A. (GAESA), a Cuban military business conglomerate that controls most of the economy. As foreign tourism increased, GAESA amassed tens of billions of dollars in profits for the regime while economic conditions continued to deteriorate for the average Cuban.

When the COVID-19 pandemic hit the island, the regime used the virus as an excuse to confine Cubans to their homes and undertake a campaign of arbitrary arrests. By July 2021, these repressive measures and the regime’s economic failures resulted in the largest protests in two decades. Tens of thousands of Cubans took to the streets demanding freedom and basic necessities. The regime detained thousands of people, subjecting many to torture and abuse. Since the July 11 protests, nearly two million Cubans have fled the island, almost a fifth of the pre-pandemic population.

Even in a hobbled state, the anti-American regime in Havana remains a significant national security threat to the United States. Cuban intelligence facilities that once hosted Soviet spies now provide China and Russia with an unrivaled vantage point to monitor the headquarters of U.S. Southern Command, U.S. Central Command, and U.S. Special Operations Command (all within 400 miles of Havana). Cuba also remains a state sponsor of terrorism and has reportedly acquired attack drones that could reach Florida.

President Trump’s decision to order the capture of Venezuelan dictator Nicolás Maduro on January 3 deprived Havana of its most important patron overnight. Since 2000, the socialist regime in Venezuela has provided Cuba with $64 billion of oil aid in exchange for Cuban intelligence fully embedding itself into Venezuela’s security apparatus. With Maduro in a New York City jail cell and 32 Cuban officers returned to the island in boxes, the Trump administration created a once-in-a-generation opportunity to seek political and economic change in Cuba.

The corrupt ruling clique led by the Castro family now faces its greatest crisis since the fall of the Soviet Union. Shortages of basic necessities and almost continuous blackouts have brought the Cuban people back to the streets and dried up tourism. At 94 years old, Raúl Castro finally faces a U.S. indictment for ordering the murder of four Americans in the 1996 Brothers to the Rescue shootdown. And new U.S. sanctions on GAESA and senior officials threaten to cut off the flow of hard currency into regime coffers.

Here’s how the Trump administration can make this pressure campaign successful.

First, keep the threat of military operations on the table. President Trump’s willingness to use force in Venezuela and Iran instills fear in the Cuban regime that it could be next. Indicting Castro certainly raises the prospect of a similar fate to Maduro and Manuel Noriega. That fear should be leveraged to obtain concessions on key U.S. priorities, including political change and the presence of adversary intelligence facilities on the island.

Next, permanently cut off the regime’s access to cash. Like its friends in Tehran, Havana has a history of using negotiations and outside aid to buy time and avoid making tough choices. The goal of U.S. economic pressure should be to deny the regime access to foreign revenue and to convince it that this pressure will not be lifted until political and economic change comes to the island.

To achieve this goal, the Trump administration should leverage the president’s May 1 executive order to threaten and, if necessary, impose secondary sanctions on foreign financial institutions and firms that continue to do business with GAESA and other organs of the regime.

Under communist rule, the Cuban people have suffered for 67 years under a party elite that prioritizes staying in power and aligning with leftist regimes over providing a better future for the island. With President Trump and Secretary Rubio committed to Cuba Libre, the bill for those decisions is finally coming due.

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Connor Pfeiffer is senior director of government relations at FDD Action and a former policy advisor in the U.S. Senate and House of Representatives who focused on Western Hemisphere and international economic issues.

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It’s Time For Castro To Clock Out