How a Rhodes Scholar with Cuban Ties Organized Hasan Piker’s Havana Convoy

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SouthernWorldwide.com – When U.S. President Donald Trump intensified sanctions against Cuba’s communist government earlier this year, Twitch streamer Hasan Piker sought advice from a friend.

Piker recalled in an online interview, “I reached out to my friend, David Adler, and said, ‘What do we do?’ He replied, ‘I’m already working on it.'”

What followed, according to Piker’s account, was the organization of a multinational convoy. This convoy transported hundreds of activists, politicians, journalists, and organizers from numerous countries to Cuba, delivering an estimated 40 tons of supplies. The initiative was branded as the “Nuestra América Convoy,” or “Our America Convoy.”

Public attention surrounding the trip has primarily focused on CodePink, Piker, Shanghai-based American Marxist tech tycoon Neville Roy Singham, and Singham’s wife, Jodie Evans, who posted a photo with Piker in Havana. On Monday, Piker drew the attention of U.S. officials by stating his belief that the “real goal” of the Treasury Department investigation is Singham, due to his funding of “political operations” in the U.S.

However, an analysis of hundreds of hours of Piker’s livestreams and interviews, compiled by computer engineer Jennica Pounds, a data scientist known online as “Data Republican,” repeatedly highlights a less recognized organization that played a crucial role in planning the mission: Progressive International, led by Piker’s friend, Adler.

“What makes Progressive International so dangerous is that, by co-opting progressive values, it provides political legitimacy to authoritarian regimes with longstanding records of repression and gross human rights violations, and whose purpose is to destroy the United States,” stated Gelet Martinez Fragela, a Cuban American journalist based in Boca Raton, Florida.

Martinez Fragela, who was born in Cuba, has spent years investigating the Cuban government’s influence in the Western Hemisphere. She maps the networks it builds with activists, nonprofits, and governments to garner support for the Communist Party of Cuba. Her website, ADNCuba.com, is inaccessible within the island.

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Founded in 2020, Progressive International originated from a political initiative launched by Democratic Senator Bernie Sanders, a member of the increasingly influential Democratic Socialists of America, and former Greek Finance Minister Yanis Varoufakis, a far-left politician. This initiative followed a gathering of activists in Burlington, Vermont, from November 29 to December 1, 2018, where organizers called for a new “international progressive movement.” Adler was present at this meeting.

At the core of the organization is Adler, who was born in Encino, California. He graduated from Brown University, where he was a Rhodes Scholar, and studied political economy at Oxford University. He previously served as policy director for Varoufakis’ “Democracy in Europe Movement,” known as “DiEM25,” and was part of Sanders’ foreign policy advisory team before becoming the general coordinator of Progressive International.

In 2024, Germany barred Varoufakis from entering the country for leading polarizing anti-Israel protests with local Palestinians. Varoufakis wrote that the decision reflected Germany’s “turn to repression.”

According to public records, Adler holds a unique position within the Cuba solidarity movement, maintaining close ties with the Communist Party of Cuba. Last year, Cuban President Miguel Díaz-Canel publicly supported Adler when Israeli authorities detained him as he joined a flotilla to Israel, purportedly carrying “aid” to Palestinians in Gaza. Adler, an American Jew, shared a video of himself from the boat awkwardly calling his parents to inform them of his participation in the flotilla to Gaza.

Qatar’s state-funded anti-Israel television network, Al Jazeera, shared the video on social media, accompanying it with childhood photos of Adler and its own propaganda narrative, stating, “David Adler called his parents from the deck of a flotilla boat to tell them he had joined the mission to Gaza. He is one of many Jewish activists who say they can no longer stay on the sidelines.”

Similarly, the convoy to Cuba was promoted globally from Havana with an anti-U.S. propaganda theme, criticizing American “imperialism.”

During the convoy’s visit to Cuba in March, Adler was seen in a VIP seat next to Díaz-Canel. The president listened attentively to Adler and later raised his fist in the air during an event sponsored by the Cuban Institute of Friendship with the Peoples, known as ICAP.

For generations, activists have traveled to Cuba through labor brigades, educational exchanges, solidarity delegations, and political tours organized by institutions linked to the Cuban state. These include ICAP and the Venceremos Brigade, which is now a fiscally sponsored project of the People’s Forum within the Singham network. The Venceremos Brigade is currently led by Fernando González Llort, one of the “Cuban Five” intelligence officers convicted in the United States on espionage-related charges.

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An advisory council for Progressive International includes Mariela Castro Espín, a member of Cuba’s National Assembly and the daughter of former Cuban leader Raúl Castro. She was indicted earlier this month by the U.S. for murder.

“The fact that Mariela Castro has a position of power with Progressive International is not insignificant,” commented Martinez Fragela, the Cuban American journalist. “In plain terms, it means that a member of the Castro family, a senior figure within the Cuban Communist Party, a member of Cuba’s National Assembly of People’s Power, and part of the broader Cuban political apparatus is involved in guiding the direction of the organization.”

In one interview, Piker described himself as “good friends” with Progressive International organizers. In another, he named Adler and Varoufakis when discussing the organization. Adler later appeared on Piker’s livestream, where Piker referred to him as “someone who I have the honor of calling a comrade.”

Adler responded, “Thanks, brother. It’s a pleasure to be here.”

The organization’s involvement in the March convoy was substantial.

The Nuestra América Convoy was not a spontaneous trip. Progressive International described it as an international operation involving approximately 650 delegates from 33 countries and 120 organizations. The mission utilized charter flights, maritime flotillas, and aid shipments carrying food, medicine, medical supplies, and solar panels to Cuba.

Piker documented a portion of the operation himself, and part of his defense against scrutiny for traveling to Cuba is that he went as a “journalist.”

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In his Cuba documentary, he showed himself boarding what he described as a “special plane” departing from Miami. This was the same plane that CodePink’s Benjamin filmed as the one CodePink’s delegation was using to fly to Cuba. In the film, Piker credited Progressive International, CodePink, and the ANSWER Coalition for organizing the effort.

“Shout out Code Pink, Answer Coalition, Progressive International,” Piker stated. “They set up a flight with medical aid, solar panels, food, numerous things that the Cuban population desperately needs.”

Participants included former British Labour leader Jeremy Corbyn, CodePink activists, labor organizers, international delegates, and public figures from various countries. Before traveling, Piker mentioned consulting Ben Rhodes, former deputy national security adviser to President Barack Obama and a key figure in the administration’s Cuba normalization efforts.

“I had talked to Ben Rhodes prior to going,” Piker said. “And he said to me like, ‘You’re going to be very sad when you see it.'” Piker recounted this story in multiple interviews and public appearances after his return from Havana.

Upon arriving in Havana, Piker stated he largely embedded with “Belly of the Beast,” a media organization named after a term used by communists and the far-left to describe operating within the U.S., which they refer to as the “beast” in their propaganda.

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“I locked in with Belly of the Beast,” he later said. According to public records, the Center for American Documentary Inc., a 501(c)(3) nonprofit based in Newton, Massachusetts, serves as the fiscal sponsor for Belly of the Beast Films LLC, located in Ketchum, Idaho. Tax filings indicate that the Center for American Documentary provided Belly of the Beast with $188,043 in 2024 for “film production services.”

Piker’s subsequent propaganda documentary from Cuba features interviews with several senior Cuban officials and institutional leaders, including Carlos Fernández de Cossío, Cuba’s vice minister of foreign affairs. De Cossío is one of the country’s highest-ranking diplomats, representing the Communist Party of Cuba. Piker also interviewed officials associated with Cuba’s international medical missions and researchers in the country’s health-care and energy sectors.

The convoy itself mirrored a model that has been part of the Cuba solidarity movement for decades.

Investigators examining the modern Cuba solidarity movement increasingly view the Nuestra América Convoy as the latest development of this infrastructure. It uses the guise of “humanitarian aid” for political advocacy, propaganda dissemination, and activist networking within a single international operation.

The trip to Cuba was just one facet of Progressive International’s activities.

In October 2025, when Adler participated in the Global Sumud Flotilla to Gaza, he was detained by Israeli authorities after vessels attempted to challenge Israel’s blockade. Following his release, Adler appeared on Piker’s livestream and discussed another Progressive International initiative known as the Hague Group.

“One of the things that we do at the Progressive International is help to coordinate a group that’s called the Hague Group,” Adler told Piker’s audience. He described it as a coalition of countries committed to taking action in support of international law and the Palestinian cause.

By March 2026, the Hague Group had expanded into a coalition of approximately 40 countries, coordinated through Progressive International’s organizational framework.

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This overlap demonstrates how the same organization that facilitated Piker’s trip to Cuba also operates across a broader network of international campaigns involving Cuba, Gaza, and anti-sanctions activism.

Federal investigators are not scrutinizing protected political speech. Across thousands of transcripts, Piker consistently characterized the Cuba trip as a “humanitarian” mission and repeatedly asserted that participants traveled under Treasury-authorized procedures. He has publicly maintained that he signed OFAC paperwork and adhered to federal requirements.

Instead, investigators are examining communications, financial records, travel logistics, and potential contacts with Cuban government personnel or entities associated with the convoy, according to sources familiar with the inquiry.

For investigators, the significance of the convoy extends beyond the journey of a single influencer to Havana.

The same organizations that orchestrated the March mission—Progressive International, People’s Forum, CodePink, and the ANSWER Coalition—consistently appear throughout the broader Cuba “solidarity” infrastructure. What began decades ago through organizations like ICAP and the Venceremos Brigade now operates through a modern network of nonprofits, media projects, international delegations, activist campaigns, and political organizations.

The March convoy that brought Piker to Cuba represents one of the most visible examples of this system in action, according to Cuban Americans who oppose the regime.

And, to them, Piker’s “comrade,” Adler, symbolizes a critical component of the network attempting to sustain communism in Cuba.