After fatally shooting a man in the head in Brooklyn in 1996, Orville Etoria was convicted of murder and given a prison sentence of 25 years to life. During his incarceration, Mr. Etoria, a Jamaican citizen with legal residency in the United States, was ordered deported by an immigration judge.
But upon his release in 2021, immigration officials allowed him to stay in America, provided he complete annual check-ins with the authorities.
To those close to Mr. Etoria, 62, it was a reprieve that gave him a second chance at life. He earned a bachelor’s degree while behind bars, successfully completed parole after he got out, got a job at a men’s shelter and started pursuing a master’s degree in divinity.
To those who support President Trump’s stated mission to deport the “worst of the worst” and other immigrants in record numbers, Mr. Etoria is exactly the kind of dangerous felon who should be expelled from the United States.
In July, Mr. Etoria became a target of Mr. Trump’s immigration crackdown. He was among five men with criminal records deported to a prison in the kingdom of Eswatini, a southern African nation where none of the men hold citizenship. A Trump administration official called them “barbaric” and said that the men’s home countries had refused to accept them.
Mr. Etoria’s case represents a tension at the heart of the administration’s deportation agenda. Some legal experts argue that there is little justification for sending immigrants to far-flung countries where they have never been and can be detained indefinitely without charges, as is the case for Mr. Etoria. These critics argue that the administration is unnecessarily putting deportees at risk by sending them to unfamiliar nations where they have few prospects or access to due process, instead of simply sending them home.
In a statement to The New York Times, the Department of Homeland Security countered that Mr. Etoria should have been deported long ago. “Our message is clear: Criminals are not welcome in the United States,” the statement said.
Mr. Etoria has not seen a lawyer since his arrival in Eswatini, his lawyers say, and family members say they have had little contact with him and are worried about his condition.
Mr. Etoria’s aunt Margaret McKen asserted that he should have been deported to Jamaica, where he holds a valid passport.
“It’s inhumane,” she said. “He paid the penalty for what he did. Why is he in prison again?”
Neither Eswatini nor the United States has explained why Mr. Etoria is being held despite completing his sentence in America and not being accused of any new crimes.
Since the early days of Mr. Trump’s second term, his government has brokered deals with countries to accept deportees from other nations. Immigration officials have instituted new rules that allow these third-country deportations from the United States in as little as six hours.
Some experts say the policy is part of an effort to encourage people to leave the United States voluntarily or risk being sent to a distant, unknown land. The administration has already sent foreign nationals to third countries that have concerning human rights records, including El Salvador and South Sudan.
In its statement, D.H.S. warned that immigrants who commit crimes in the United States should expect to “end up in CECOT, Eswatini, South Sudan, or another third country.” (CECOT is a notorious prison in El Salvador.)
The Eswatini government at one point requested a half-billion dollars from the United States in exchange for taking in third-country deportees, according to documents obtained by The Times.
The documents indicate that Eswatini was willing to take more than 150 people from other nations for a cash payout of more than $10 million from the United States.
Eswatini officials also asked whether the United States expected deportees to be put on trial and sentenced by local officials once they arrived.
A spokeswoman for Eswatini’s government declined to comment on the details outlined in the documents, including on the amounts of money involved.
Immigration records show that Mr. Etoria was ordered deported in 2009, while he was still incarcerated. Matthew Hudak, a former senior official with the U.S. Border Patrol, said that if foreign nationals completed their sentences in the United States, immigration officials should work to deport them.
“When someone makes the decision to leave their home country,” he said, “they are agreeing to subject themselves to the laws of the country they are entering.”
Jamaican officials said it was untrue that their country had been unwilling to take Mr. Etoria. “Our position is that we do not refuse any of our nationals, regardless of whatever they have done,” Joan Thomas Edwards, Jamaica’s top diplomat in southern Africa, said in an interview this month.
Representatives of the Jamaican government visited Mr. Etoria in the Eswatini prison on Aug. 21, according to a statement from the island’s foreign minister. The minister, Kamina Johnson Smith, said Mr. Etoria was in good spirits and receiving necessary medical attention. The government was working to get him returned to Jamaica, she said.
Officials with the International Organization for Migration also visited Mr. Etoria and the other deportees last month at the request of Eswatini’s government, offering them humanitarian assistance and support in returning to their home countries if they want to, a spokeswoman for the organization said.
Mr. Etoria came to the United States on a green card in 1976 at age 12. He joined his mother, who had been sponsored by a family she worked for as a nanny, said Ms. McKen, his aunt. He had tough times early in life, she said. He saw his mother flee from his abusive father. In the United States, he struggled to adjust and was bullied in school, she said.
Mr. Etoria has a history of drug abuse, which he has blamed in part on head injuries he suffered as a child. He was also diagnosed with schizophrenia. Doctors noted that he has exhibited violent outbursts, hallucinations and paranoia, according to court records.
He was arrested in 1981 on charges of attempted murder, robbery and kidnapping. During a psychiatric evaluation, he said he could not remember exactly what happened, according to court records. He pleaded guilty and served three years in prison.
More than a decade later, Mr. Etoria walked into a leather goods shop and shot the victim three times in the head, according to Brooklyn court records. The motive was never determined, and there was no indication that he knew the victim or that the crime was gang-related.
During his testimony at a 2003 appeal hearing, Mr. Etoria said he did not remember what happened because he was on drugs at the time and suffered hallucinations in the days leading up to the shooting.
Since leaving prison in 2021, Mr. Etoria, a father of three adult children, has spoken regularly with his aunt, she said. He has discussed his job at the shelter, and how he was learning to use the computer.
“He was finally getting some clarity on his life,” Ms. McKen said. “I would say, finally becoming human again.”
When he went for his annual check-in with immigration officials in June, they took him into custody, said Mia Unger, a lawyer with the Legal Aid Society in New York, which is handling Mr. Etoria’s case.
Ms. McKen said she tracked her nephew’s movements on the government’s online immigration database after he was detained. She saw that he was moved to a detention facility in upstate New York, then to Louisiana, then to Texas. On June 26, Mr. Etoria called one of his sons and told him that he had been put on a plane to Jamaica, but was removed without explanation before it took off, according to Ms. McKen.
A few weeks later, Ms. McKen said, Mr. Etoria’s name no longer appeared on the database. After a few days, he resurfaced on the administration’s list of men deported to Eswatini.
Jonah E. Bromwich contributed reporting from New York. Camille Williams contributed reporting from Kingston, Jamaica. Sheelagh McNeill contributed research.
John Eligon is the Johannesburg bureau chief for The Times, covering a wide range of events and trends that influence and shape the lives of ordinary people across southern Africa.
Hamed Aleaziz covers the Department of Homeland Security and immigration policy for The Times.
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