News has reached Guanajay maximum security prison, southwest of Havana, and is being discussed among inmates: one of their own, rapper Maykel Osorbo, could be back on the streets in two weeks. This is the deadline that, according to State Department sources who spoke to the American media outlet USA Today, Washington gave the Havana government as part of ongoing negotiations. Osorbo acts as if nothing new is happening. There have been other releases, other pacts with the Vatican or with the Americans, other moments when it seems something is going to happen with him, without anything ever materializing. When Cuba announced the release of more than 500 prisoners in early 2025, Osorbo’s friends (an artistic name that alludes to bad luck in the Yoruba language) asked him if he harbored any hope of being one of those listed. “I don’t have luck,” he said. “Nothing good has ever happened to me”.
This Tuesday, in a hurried call from prison, Osorbo, who is serving a nine-year sentence of deprivation of liberty, assured EL PAÍS that he preferred not to spend hours thinking about the moment they might release him. “I’m calm, in my corner, waiting,” said the rapper. If that were the case, if as part of the dialogue between Havana and Washington Cuban authorities were to release their more than 700 political prisoners, Osorbo would remain the same: “If I leave here alive, I will continue to be what I already am, a musician, a Cuban who had a difficult life and got up a thousand times. But if they decide, out of malice, that I must remain imprisoned, then they will have to kill me”.
His name and that of artist Luis Manuel Otero Alcántara, Cuba’s most recognized political prisoners, came up in the secret meeting that took place on April 10 in Havana, the first delegation to fly from Washington to sit down and dialogue with the Cubans since the Obama era. Donald Trump entered the new year with the capture of Nicolás Maduro, meddled in a draining war with Iran, and has finally said he intends to bring about a “new dawn for Cuba”.
Among other important matters at the negotiating table, this month’s meeting on the island addressed the issue of Osorbo and Otero: two artists, both Black, poor people from Old Havana. One in Guanajay maximum security prison, the other in Kilo 5, in Pinar del Río. One a winner of two Grammys, the other featured among the 100 most influential personalities by Time magazine.
Osorbo is serving nine years in prison for the crimes of “disobedience, resistance, and contempt”. Otero, five for the crimes of “assault, contempt, public disorder, and incitement to commit crimes”. Years before going to prison, both had already garnered the attention of all Cuba for their constant denunciations of Decree 349, a government censorship mechanism to regulate artistic creation in the country; or because they put their bodies on the line to make state repression visible; or because they barricaded themselves in the headquarters of the San Isidro Movement and led the hunger strike that mobilized international attention and exposed how a government was capable of suffocating young people and artists. The day Cuban authorities understood that the freedom these individuals practiced and offered to the rest of Cubans was a danger, they locked them in their prisons.
Even so, earlier this month, when American journalist Kristen Welker disembarked with her Meet the Press team from NBC News at the José Martí Memorial facilities, President Miguel Díaz-Canel —who, more than ever before, has been granting interviews to major media outlets given the uncertainty of tensions with the United States and the need to reaffirm as president of Cuba the man they allegedly wanted to remove from the political scene— denied not only that Osorbo was a political prisoner, but also that such a thing as prisoners of conscience existed in Cuba.
“I believe we must overcome, Kristen, an entire paraphernalia of concepts that has existed regarding issues about Cuba, about democracy, human rights, whether we are a tyranny or a dictatorship,” Díaz-Canel assured the journalist, who again preempted him by saying that there were more than 1,200 political prisoners on the island, including rapper Osorbo, “who is imprisoned and has won two Latin Grammys”. Díaz-Canel smiled, and let her know that it was nothing more than “prejudices”. “Not everyone in Cuba is in favor of the Revolution. There are people who do not embrace the Revolution, who every day express themselves in different ways against the Revolution and are not imprisoned. That image that in Cuba everyone who speaks against the Revolution is imprisoned and is a political prisoner, is a lie, it is a slander”.
Osorbo and Otero, two marked lives
When he was ten years old, Osorbo’s mother left the house as if going to the corner, without telling him. The child did not see her again for two decades. She had taken to the sea, as part of the stampede in 1994 known as the Rafter Crisis, in which more than 35,000 Cubans fled to Miami. His paternal grandmother took over his care. But “when a mother is missing, everything is missing, and a large part of the deviation I had was the lack of a mother,” the rapper said in a video published on his Facebook profile five years ago. Osorbo’s life since then has also been a long journey through the country’s prisons or juvenile re-education centers. He has spent almost half his life passing through these places.
“I was always a Black man from Old Havana. Without clothes, without shoes, just normal, in the park, talking to this one and that one, just another Cuban from the neighborhood,” he tells EL PAÍS. “The government was the one that turned me into a threat, because for them, poor Black people are a threat when we tell them what they’ve done wrong. They fear us”.
Otero also grew up in a humble family in the El Cerro neighborhood. In a conversation days before his arrest in 2021, he recounted how he had made himself the person he is today. “I didn’t study at any academy, nor did anyone give me anything; I wasn’t anyone’s son, nor was I placed in the Superior Institute of Art. I am a Black kid from El Cerro who has achieved the love of a lot of people and the connection of a lot of people by working and with a way of doing things”.
Art came into Osorbo’s and Otero’s lives self-taught. Five years ago, in the midst of Cuba on the brink of what has been its greatest crisis of all time, both began to gain notoriety for their constant denunciations in public spaces, which then jumped to social media. Both were arrested in 2021, when the country was a hotbed amidst the accelerated health collapse with the coronavirus crisis, the closure of tourism, the consequent blow to the economy, and a state of lack of all kinds of freedoms. The context had led to many expressions of discontent among Cubans.
On several occasions, the artists were arrested and then released. On the afternoon of March 18, 2021, the political police entered Osorbo’s house and took him away barefoot and shirtless, while he was having lunch. His whereabouts were unknown until several days later, when the UN declared him disappeared.
On July 11, 2021, Otero was surprised to see many people in the streets. “I left without a phone, disconnected from everything, until today,” he said in an interview last year with EL PAÍS. “That is one of the happiest days of my life. At that moment I said: ‘Good, now it really fell.’ And the patrol driver told me: ‘But you won’t be there’.” It was the largest anti-system protest since the Revolution came to power, which turned thousands of citizens into political prisoners, including Otero.
Prison has not been the artistic death for either of them. With the song “Patria y Vida” (Homeland and Life), which has become an anthem for the liberation of Cuba, Osorbo, one of the authors, received two Latin Grammys for the titles of Best Urban Song and Song of the Year. Rapper Eliexer Márquez Duany, El Funky, who knew Osorbo since elementary school and is a co-author of the song, regretted not having gone with him to collect the award at the Latin Academy of Recording Arts & Sciences gala in Miami. “I play that song and the first thing that comes to mind is Maykel,” says El Funky now. “We made it together, it was always our dream. Rap has been everything for Maykel, it has saved him from many things”.
In September 2021, Otero’s face appeared among the 100 most influential personalities in Time magazine, alongside Russian opposition leader Alexei Navalny, pop star Britney Spears, tennis player Naomi Osaka, and Puerto Rican singer Bad Bunny. They thus recognized an artist’s constant struggle against totalitarian power.
“Luis has not only had to make his way in a system that limits freedom of expression, but he has had to do so facing surveillance, censorship, harassment, and, finally, the deprivation of his liberty. Luis has become a symbol because his case condenses many of the tensions of the current Cuban context: the relationship between art and politics, between body and power, between visibility and punishment,” said art curator Claudia Genlui, the artist’s ex-partner and who helps him with his art from exile. The artist, who has not stopped creating from his cell and has staged six hunger strikes in detention, is officially reaching the end of his sentence next July.
“Luis is a person with a life, with affections, with a history that has been violently interrupted. His release should mean, above all, the possibility of recovering that life,” says Genlui. “His freedom is a right that should never have been taken from him”. However, the art curator focuses on the context in which this release takes place, if Otero is finally released in two weeks, as the information leaked from the State Department indicates. “If it is part of a political negotiation, that opens important questions about the conditions, about the subsequent fate, about what those forms of forced exile imply”.
Guarantees for release
Amidst the negotiations between high-ranking officials from Havana and Washington, of which very little is officially known, several human rights organizations and groups have focused on insisting on the release of the hundreds of political prisoners who remain in prisons across the country. In the context of these dialogues, two releases have taken place, although the Cuban government has never publicly acknowledged that they are part of any negotiation with the Americans. Rather, they have denied that they are being given any kind of ultimatum to release their political prisoners.
Of the first of these releases, carried out in March, only 27 political prisoners benefited, out of a total of 54 released. Of the second round, in which 2,010 prisoners were released in April, “there was not a single political prisoner,” assures Javier Larrondo, director of Prisoners Defenders, an NGO that documents the cases. Rather, since it became known that Washington officials were at the table with representatives of Castroism, the regime has not stopped fabricating new political prisoners, imprisoning citizens for protesting or expressing public discontent. Since March, Cuban civil organizations have registered the detention of at least 28 new people for political reasons.
Reality shows that, as has happened before, there is no security for prisoners of conscience who may be released as part of a diplomatic agreement. “They don’t have many guarantees. Several political prisoners who have benefited from early releases, either with conditional liberty or extra-penal license, or even when they have received pardons, have later been imprisoned again,” explained lawyer Raudiel Peña Barrios, a member of the legal advisory group Cubalex, who highlights that if Osorbo, Otero, or any other political prisoner were released, they could end up back in prison the moment they begin to exercise their rights to freedom of expression. “They do not have full guarantees that they cannot be imprisoned again”.
Therefore, Camila Rodríguez, director of Justicia 11J, a working group that documents human rights violations in Cuba, insists that in any dialogue, the premise that the process of releasing political prisoners must be full, unconditional, and with real guarantees of non-repetition should not be missing. “It is not enough to have releases under formulas that keep the sanction in force, because that leaves people in a situation of permanent vulnerability,” she says. She also believes that civil society groups in charge of political prisoners, the families of the detainees, should participate in the process, and demands the publication of lists that guarantee the clarity of the releases, something that has not happened in the past. “In that context, any new dialogue should focus not only on how many people are released from prison, but on how those decisions are made, who participates in them, and what guarantees exist for that freedom to be real and lasting”.
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