America dealt with a Nicaraguan dictator. It didn’t go as planned.

The Biden administration thought its pressure campaign on Nicaragua might be getting some traction when the Central American country’s authoritarian government handed over 222 political prisoners to the United States last month.

The hopes didn’t survive long. Almost immediately, Nicaragua stripped the ex-detainees of their citizenship, threatened to seize their property and sentenced a Catholic bishop who declined to leave to 26 years in prison. So much for a possible rapprochement with Washington or political softening in Managua.

The moves by Nicaraguan President Daniel Ortega and Rosario Murillo — his powerful wife and vice president —now seem more like a way to consolidate power and continue repression than make amends with Washington.

“For the prisoners, it’s good. For the country, it sucks,” said Eddy Acevedo, a Republican former Capitol Hill staffer who has helped craft U.S. policy on Nicaragua over the past seven years. “Ortega just deported his whole opposition. What happens if this gets replicated in other countries?”

The U.S. will keep on or possibly intensify the pressure campaign on Nicaragua, maybe adding new sanctions, say Biden administration officials. Yet America is struggling to protect and promote democracy not just in Nicaragua but across Latin America. Democracies in Peru and Brazil have wobbled. Relations with Mexico are strained. These diplomatic challenges for Washington come at a time when China and Russia, its chief global rivals, are making in-roads in the region.

“We’re already seeing a troubling drift toward authoritarianism and deliberate attacks on democratic institutions in Nicaragua’s neighbors, such as Guatemala and El Salvador,” said Rebecca Bill Chavez, a former Defense Department official in the Obama administration.

Nicaragua is a test case. Washington has devoted a lot of effort both to weaken and sway the Ortega regime, but has come short of its goals — a situation likely being watched by others in the region.

Some of the prisoners now released in America are urging the Biden administration to keep up the pressure on the dictatorship they hope to weaken from abroad.

“We were not the most important part of the story,” said the newly freed Juan Sebastian Chamorro, a former Nicaraguan presidential candidate. “The most important part of the story is that there are no liberties in Nicaragua. There’s no freedom. There’s no democracy.”

A bad relationship turns toxic

U.S.-Nicaragua links began unraveling more than a decade ago as it became clear that Ortega — a former rebel who fought another Nicaraguan dictator — wouldn’t leave the presidency. Relations worsened over the past five years as Ortega and Murillo strengthened their grip.

The Trump administration imposed economic sanctions and other penalties, mainly targeting individuals such as Murillo, in 2018, a year when the regime brutally cracked down on widespread protests.

In June 2021, Secretary of State Antony Blinken told his Nicaraguan counterpart that the United States could ease up on those penalties if Nicaragua were to move back toward democracy and improve its human rights record. (Abuses such as torture and extrajudicial executions in Nicaragua may constitute crimes against humanity, a U.N. investigative panel said earlier this month.)

Blinken’s message failed to sway the ruling power couple. Over the next few months, Ortega and Murillo imprisoned more dissidents ahead of an election.

The U.S. responded by slapping sanctions on a Nicaraguan state-owned mining company and banning visas for hundreds of Nicaraguan officials and their relatives. Biden also issued orders in October that authorized his administration to impose future sanctions on various economic sectors in Nicaragua, as well as trade and investment.

This was a major threat because it would, effectively, circumvent a trade deal between the United States, Nicaragua and a number of other countries. The United States is Nicaragua’s largest trading partner.

A no-brainer operation

On Jan. 31, Murillo called U.S. Ambassador to Nicaragua Kevin Sullivan and urged him to get in touch with the foreign ministry for a matter that could improve ties.

Ten days later, the 222 prisoners landed in the Washington area. According to three U.S. officials familiar with the issue, Nicaragua demanded nothing in return.

Biden aides saw taking the prisoners as a humanitarian no-brainer — so non-controversial that it was largely handled at the assistant secretary level, according to a senior National Security Council official. Biden was kept apprised throughout, a second senior NSC official said. The NSC officials, like other U.S. officials quoted, were granted anonymity to describe sensitive diplomatic matters.

Multiple U.S. departments were involved in the logistics, including screening the prisoners for security risks and preparing mental health services for those who might need them. They rejected a handful of people on the original list of 228. Two people, including Catholic Bishop Rolando Alvarez, declined to go to the United States.

Biden administration officials knew that Ortega and Murillo could benefit by putting distance between themselves and their rivals. But the opposition hadn’t been able to do much inside Nicaragua because all the key figures were in prison.

One of the prisoners described being awakened by guards in the early morning on Feb. 9 and told to dress and be ready in 10 minutes. The prisoner and fellow detainees then boarded buses with windows covered by bars and wood. They were told to keep their heads down and mouths shut.

Toward the end of the road trip, guards on the bus handed the prisoners papers to sign. It was dark and some prisoners were reluctant to sign a document they could barely see. The guards told them that if they didn’t sign, they wouldn’t be able to leave the country. That was the first clue many prisoners had that they could soon be free.

Once the prisoners were let off the buses, they saw they were on the tarmac of the airport, next to a massive plane. “We saw a box on the tarmac that had the passports of all of us — new Nicaraguan passports,” said the former prisoner, who was granted anonymity to protect their family in Nicaragua. “This was quite an operation.”

Searching for rifts

The prisoner release could be a sign of dissension within the ruling ranks. A video said to be from late December appeared to show Ortega and Murillo parting after a disagreement, spurring ongoing speculation about a rift between the pair. After the release of the prisoners to the United States, Ortega appeared to suggest the idea came from his wife.

Reports last spring that Laureano Ortega, the child thought most likely to succeed the ruling couple, had reached out to U.S. officials about sanctions relief also led to questions about potential tensions within Nicaragua’s elite. This all comes amid speculation that Daniel Ortega’s health is failing and a lack of clarity about how loyal his supporters are to his wife.

Ortega and Murillo were once leaders in the Sandinista rebel movement, helping topple the dynastic autocracy of Nicaragua’s Somoza family. Today, they have turned into what they once loathed, their critics say.

After revoking the citizenship of the exiled dissidents, at least one of whom also has American nationality, Nicaragua’s government also stripped 94 other people of their Nicaraguan passports. Many of the latter are activists living outside the country.

Nicaragua’s ambassador in Washington did not respond to requests for comment.

Limits of U.S. power

Still, America’s options in Nicaragua are limited.

Increasing sanctions pressure could damage Nicaragua’s economy and worsen the migration crisis in the hemisphere.

Ortega and Murillo have other potential options for international support — Russia and China. The regime supports Russia’s war in Ukraine and has permitted Moscow to place troops and military equipment on its soil. In late 2021, Nicaragua switched its diplomatic recognition away from Taiwan in favor of Beijing, in a sop of the Chinese.

Hawkish figures such as former Trump administration national security adviser John Bolton have called Nicaragua, Cuba and Venezuela the “troika of tyranny” because of their repressive rule. The United States has taken particularly harsh measures toward each, with little success.

The Cuban communist regime has survived decades of U.S. sanctions. Biden has yet to embrace a brief diplomatic flowering of relations with Havana that began under then-President Barack Obama but was ended by then-President Donald Trump.

The Venezuelan regime of Nicolas Maduro, too, has weathered years of sanctions and other U.S. pressure. A U.S.-backed opposition effort to overthrow Maduro has largely fizzled in the past six months, and the dictator appears secure.

Some of the former Nicaraguan prisoners already are in touch with each other, looking at uniting around a common platform to oppose Ortega and Murillo from exile. “This is one of the mistakes Ortega made — he made us closer,” said Chamorro, the former presidential candidate.

Yet diaspora-led opposition movements are rarely successful, noted Christopher Sabatini, a Latin America analyst with Chatham House.

Such campaigns “don’t command the resources, they don’t command diplomatic legitimacy … they’re often very fractious,” Sabatini said. Inside Nicaragua, “there’s not going to be a popular uprising that unseats Daniel Ortega at this point. There can’t be. There’s no one to lead it.”