Last week, the State Department released a report detailing decades of Cuban espionage and its collaboration with far-left radical organizations in America. The report, which implicated dozens of groups and individuals, is just the latest in a push by the department to counteract Cuban influence.
That effort has included new sanctions and a high-profile investigation that reportedly has included DSA-aligned streamer Hasan Piker; Medea Benjamin, a leader of the radical antiwar group Code Pink; and as many as 40 others for their participation in a widely publicized trip to Cuba in March 2026. The inquiry, Fox News reports, centers around whether Piker, Benjamin, and others violated American sanction rules when they visited and engaged in what may have been advocacy on behalf of a designated state terror sponsor.
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Both Benjamin and Piker have portrayed themselves as innocent victims of the Trump administration. But the story of the Nuestra América Convoy they participated in offers a glimpse not only into modern Cuba advocacy but also into what could become, with interagency cooperation and sustained focus from the Trump administration, a broad-based U.S. campaign against malign foreign influence operations.
The investigation is focused on the Nuestra América Convoy, a large-scale trip to Cuba in March of this year. Organizers billed it as an effort to deliver “critical humanitarian aid” to Cuba. In practice, it also served as both a gathering for some of America’s most extreme activists and an opportunity for the Cuban government to propagandize an American audience.
Benjamin first floated the idea in December 2025, modeling the convoy on the flotillas to Gaza that have attracted international attention. Organizers appear to have formalized plans at a January 2026 meeting of Progressive International, a transnational organization of which Code Pink is a member. PI was founded by the Bernie Sanders-affiliated Sanders Institute and the Democracy in Europe Movement 2025 (DiEM25) to oppose President Trump and the rising global Right.
At the meeting, participants committed to convening the next time in Havana. That follow-up meeting would become the convoy joined by Benjamin, Piker, and others.
In March, just weeks before the convoy launched, CUNY’s Graduate Center hosted a pro-Cuban-regime conference that drew many who would later participate in the convoy. The event was attended by Leima Martínez Freire, an official of the Cuban Institute of Friendship with Peoples (ICAP)—a group that U.S. intelligence agencies and some Cuban defectors view as a front for Cuban intelligence. Freire announced that Amistur, ICAP’s travel agency, had made travel arrangements for a Progressive International delegation to Cuba, and that ICAP had scheduled a meeting with the delegation at its headquarters in Havana. (The United States formally sanctioned both ICAP and Amistur on June 4.)
Finally, in late March, dozens of progressive activists converged on Havana to “deliver aid” to the Cuban people. These included: Piker; Benjamin; People’s Forum executive director Manolo De Los Santos; Isra Hirsi, daughter of Minnesota Representative Ilhan Omar and a prominent organizer in Columbia University’s encampment protests; and Democratic Socialists of America organizer James Ray, who shared a photograph of himself outside North Korea’s Embassy in Havana.
Attendees were ostensibly there to deliver aid—one of the few reasons Americans are permitted to travel to Cuba under sanction rules. But in practice, convoy activities were not restricted to aid delivery.
“Aid delivery” was not, for example, the focus of a speech Benjamin delivered alongside Cuban President Miguel Díaz-Canel and broadcast on Cuban state media. In the speech, delivered at the convoy’s welcoming assembly, she criticized the United States. Following her were speakers who discussed their readiness to take up “AKMs” (Soviet-era rifles) to defend the island from Americans.
Code Pink’s social media also showed convoy participants painting a mural and conducting photoshoots with young children. These activities could have served as opportunities for networking, relationship-building, and training.
Code Pink has a history of questionable connections to the Cuban government. A report on Benjamin from the Network Contagion Research Institute (NCRI) outlined a relationship with the Cubans, in which coordination appears to run through Code Pink’s repeated delegations. For years, Code Pink has partnered with ICAP—the Cuban intelligence front—to organize delegations to Cuba, including a 2015 trip during which participants may have met with members of the Cuban Five spy network. Benjamin has also appeared alongside ICAP officials at joint press conferences held at ICAP headquarters in Havana, according to NCRI’s report.
These actions are part of a broader pattern by which Code Pink and Benjamin have repeatedly defended, and even sent delegations to, repressive regimes around the world. The NCRI report, for example, identifies Benjamin fielding phone calls from Press TV, a sanctioned Iranian regime-controlled news outlet, and then shortly afterward mirroring their talking points. Code Pink’s actions have prompted repeated calls from Congress asking the Department of Justice to open a full investigation into the group under the Foreign Agents Registration Act.
Piker, who traveled with the convoy as part of an “influencer delegation” organized in part by the Democratic Socialists of America, framed his participation as journalistic—a way to enter the Communist country without running afoul of sanctions. He produced a short documentary for his channel on Cuba that prominently featured regime-approved talking points, including claims about Cuba’s medical innovations, the global impact of its international medical missions, and its claimed non-adversarial history with the United States.
The documentary also highlighted China’s role in upgrading the island’s solar power capacity and gave Cuba’s deputy foreign minister extended, largely uninterrupted speaking time. The film concludes with a closeup of Code Pink and the tightly aligned group The People’s Forum, followed by a shot of a Fidel Castro billboard reading “Fidel, faithful to your legacy,” as Piker narrates the Cuban revolutionary slogan, “Patria o muerte, venceremos.”
Piker’s other activities in Cuba included partying with the pro-Hezbollah rap group Kneecap, distributing “wads of cash,” and “living large.” It’s not clear that such activities jibe with doing full-time journalistic work in Cuba. For comparison, past DSA delegations to Cuba adhered strictly to U.S. rules; members of the DSA’s National Political Committee reportedly prohibited delegates from even going to the beach.
Treasury Department subpoenas, announced in May, are the first step in determining whether participants in the convoy violated U.S. sanctions laws. Because Cuba is designated by the U.S. government as a state sponsor of terrorism, efforts to evade U.S. sanctions are subject to heightened legal and regulatory scrutiny. These prohibitions are broad: even the National Lawyers Guild—a leading far-left lawyers group that regularly provides legal services for radical protesters—is crystal clear about how easy it is to run afoul of sanctions law while in Cuba. Even trips presented as humanitarian or journalistic missions can create sanctions exposure if participants spend money at prohibited businesses or provide direct or indirect support to Cuban state entities.
“The Cuban military largely controls the most profitable elements of Cuba’s tourism sector,” said Max Meizlish, a research fellow at the Foundation for Defense of Democracies. “So the U.S government maintains a list of properties, entities, and other business ventures linked to the regime’s military, intelligence, and security services called the ‘Cuba Restricted List.’”
Benjamin, Piker, or other attendees’ activities may well have violated these restrictions. Notably, the Nuestra América convoy sent more than 20 tons of aid to Cuba with the purpose of what Reuters characterized as “circumvent[ing] U.S. sanctions.” If that’s the case, then the State Department’s investigation may lead to charges.
Both Benjamin and Piker have responded to the government’s demands with defiance. Benjamin has indicated that her organization plans to launch “encampments” this summer as a protest. She also pushed back on the requirement to complete the Treasury Department questionnaire, arguing that it constituted “intimidation” and is intended to waste Code Pink’s time and resources.
Meantime, Code Pink’s engagement with Cuba appears to have continued unabated. Benjamin recently said that the organization is shipping thousands of pounds of supplies to the country every two weeks and is preparing for upcoming travel tied to commemorative events on the island this August.
Piker has struck a similar tone. He has maintained his innocence and framed the Treasury scrutiny and the growing federal focus as politically motivated. He has not acknowledged receiving a subpoena and in fact earlier this month claimed that he had not been subpoenaed. He also continues to assert that his activities fall squarely within the scope of journalism.
Aid to Cuba that potentially violates sanctions has occasionally escaped scrutiny by overwhelming the U.S. government’s enforcement capacity. The Trump administration is shifting that landscape, as reflected in its sanctioning of ICAP and emphasis on holding the Cuban government to account in support of the Cuban people.
Meizlish described the administration’s approach as “an unprecedented U.S. sanctions enforcement against the Cuban regime,” but argued that the tougher posture is warranted.
“I think it’s a good thing for the U.S. government to be stepping up enforcement and making sure that U.S. persons aren’t providing support to a murderous regime,” he said.
While full details have not yet emerged on the targets of the U.S. subpoenas, they could signify a broader U.S. crackdown on foreign influence operations. And though Treasury has taken the first step in this case, other authorities like Florida’s attorney general or the Department of Justice could strengthen the American response. A full-court press may well be coming.