Amid its escalating economic and political pressure campaign against Havana, the Trump administration has sent 170 deportees back to Cuba, including several with criminal records in the U.S., something Cuba has traditionally rejected.

The Department of Homeland Security announced that it had sent a “plane full of deportees” back to the Caribbean island on Feb. 9, including “kidnappers, rapists, traffickers, and other criminals.” The flight marks the first removal flight to Havana this year.

For years, Cuba has paused deportations from the U.S. at will and refused to receive nationals with criminal records. Their inclusion on the recent flight comes as the United States chokes the nation’s oil supplies in a bid for negotiations that could end up in regime change, sparking questions about whether Cuba will take more deportations to ease the political and economic pressure.

In separate statements, the Cuban government said that it had received the people to comply with long-standing bilateral migration accords between the two nations. It also mentioned it had take into custody three people suspected of having committed crimes in Cuba before they left.

In its own announcement, the Trump administration featured men convicted of second-degree murder, rape, drug trafficking and other serious crimes. The Miami Herald verified some of the convictions with news reports and public records.

Among those deported on the Feb. 9 flight was Yondeivis Wongden-Hernandez, who was charged in the fatal drive-by shooting of a 17-year-old girl in a parking lot in Miami-Dade. Court records show he was convicted of second-degree murder with a weapon.

The Herald asked DHS to clarify who else was on the flight, as well as how many of the deportees had criminal convictions and what kind. The agency did not provide further examples of deportees with criminal histories beyond the ones it had already announced.

“ICE removed 170 Cuban illegal aliens including those convicted of heinous crimes including murder, rape, kidnapping, and drug trafficking to Cuba Feb. 9. If you are in the country illegally and break our laws, we will find you, arrest you, deport you, and you will NEVER return,” an agency spokesperson said in a statement.

For years, Cuban immigrants with criminal convictions have represented a policy headache for U.S. officials. They could not be deported to Cuba, because the regime in Havana would not take them. The United States has deemed Cuba a “recalcitrant country” when it comes to deportations because it refuses or delays cooperation around deportations.

But the immigrants with criminal records also cannot legalize their immigration status in the United States. That means people spend years — and sometimes decades — stuck in legal limbo.

They are ineligible to benefit from the Cuban Adjustment Act, the fast track to citizenship that allows Cubans to apply for green cards within a year of their arrival in the United States. Convictions for certain crimes, including drug trafficking, robbery, rape and murder, makes immigrants ineligible to apply through the 1960s law. They also cannot apply for other visas, like employment or family-based green cards, because of their criminal histories.

Human Rights First, an advocacy group that tracks deportation flights, found that there were 12 removal flights carrying at least 1,379 Cuban nationals last year. That number was the same as in former President Joe Biden’s last year in the White House.

The Trump administration also bussed 3,753 Cubans through the southwest border to Mexico during the same period. That includes Cuban nationals with serious criminal records who were previously impossible to deport, according to Herald interviews. The Herald spoke to six Cuban men sent to Mexico and the lawyers of another six. Some described spending weeks searching for work and food while sleeping on the street.

Many have also sought temporary housing in a migrant shelter in the city of Villahermosa. One of its administrators told the Herald that they had registered nearly 350 Cubans as of late October, including several older men with serious medical conditions.

“Many of them are Peter Pan,” the shelter operator told the Herald last year, referring to the 1960s program that brought thousands of Cuban children to the United States through the Catholic Church. “That we are getting Cubans is a very new situation.”

The arrival of the Cubans with rap sheets in Havana also coincides with intensifying pressure from the United States in a push to engage in negotiations that could ignite regime change. In recent weeks, the Trump administration has threatened tariffs on countries that supply oil to Havana and blocked oil shipments leaving Venezuela for the island.

Cuban authorities are no longer supplying international airlines with jet fuel as a result and all scheduled surgeries have been put on hold. Independent journalists and social media users have also circulated images of the oil blockade; a man buried in a cardboard box because there are no wooden coffins; people cooking on the streets with wood and coal, and backed-up piles of rotting garbage on city streets.

Cuban officials recently said they are ready to sit down with American officials and expand security cooperation and that both Havana and Washington would benefit from “constructive engagement.”

(Miami Herald staff writer Nora Gámez Torres contributed to this story.)

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