MIAMI, February 2, 2026 — A Cuban podcaster who once openly courted Donald Trump’s favor is now facing deportation after a recent surge in ICE enforcement, highlighting the precarious legal status of many Cuban migrants arriving in the U.S.
A Trump Tattoo and a Looming Threat
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The case of Oscar Alejandro, known as “El Oski,” reveals the complexities of immigration policy and the uncertain future for thousands of Cubans.
- Oscar Alejandro, a Cuban immigrant and vocal Trump supporter, is facing deportation.
- His legal status is complicated by the type of documentation he received upon entering the U.S.
- Thousands of other Cubans are in a similar situation, unable to qualify for long-term residency.
- The case underscores the shifting landscape of U.S. immigration policy toward Cuba.
Oscar Alejandro, also known as “El Oski,” arrived in Miami from Cuba in 2019. Before his relocation, he lived a life of petty crime and frequent imprisonment, but after arriving in the U.S., he became a prominent voice in anti-Cuban government circles, amplified by American media. He openly expressed admiration for former President Donald Trump, even getting a large tattoo of Trump’s face on his chest – a process that took three sessions of approximately four hours each, according to a January 15 interview with Local 10 News. He described himself as “very emotional for Trump” at the time.
The I-220A Dilemma
Now, El Oski lives in fear of deportation as U.S. Immigration and Customs Enforcement (ICE) increases its enforcement efforts. “I’m scared,” he told Local 10 News on January 15, acknowledging the risk faced by many Cubans in his situation. He is among an estimated 400,000 Cubans who entered the U.S. across the southern border and were released with an I-220A form, allowing them to remain while their cases are evaluated, but not guaranteeing a path to legal residency.
What is the difference between probation and Form I-220A in U.S. immigration law? The federal government does not recognize Form I-220A as lawful entry for the purpose of changing immigration status, according to immigration lawyer Mark Prada.
The problem lies with the Cuban Adjustment Act (CAA) of 1966, which historically offered a streamlined path to permanent residency for Cubans. However, the CAA only applies to those who entered the U.S. legally. The now-defunct “wet feet, dry feet” policy, in effect until 2017, allowed Cubans who reached U.S. soil to stay and pursue regularization. Without a legally recognized entry, obtaining a green card is impossible.
Prada estimates at least 400,000 Cubans are in this predicament. He is currently challenging Trump-era policies in court, arguing that those released into the country should be considered on probation regardless of their documentation. “It’s a problem because the government doesn’t accept it as a legal entry,” El Oski echoed in his interview with Local 10 News.
From Trump Supporter to Legal Limbo
El Oski had hoped that Trump would assist Cuban dissidents in legalizing their status in the U.S., but he expressed disappointment. “Exactly the opposite happened,” he said. “It’s not what I expected.” Despite his unwavering support, he wasn’t pardoned. Recently, ICE arrested El Oski and deported him to El Salvador, according to information shared on YouTube.
El Oski, through his podcast, often shares the experiences of other recent Cuban arrivals adapting to life in Miami. Despite his current situation, he maintains hope for both Cubans in the U.S. and those still on the island, repeatedly stating “Free Cuba,” even while advocating for U.S. intervention.
The case of El Oski raises a critical question: who is truly freer – the Cuban people facing decades of economic blockade, or a vocal supporter of the policies that perpetuate their hardship?
