The financing, coordination, and delivery of goods crossed legal lines
Treasury Department subpoenas target two prominent activists for their participation in a March Cuba delegation that allegedly violated U.S. sanctions through financial transactions and goods delivery. Investigation encompasses approximately 40 American citizens and 145 nonprofits with $1 billion in revenues, reflecting broader federal scrutiny of foreign influence operations and pro-communist activist networks.
- Treasury Department subpoenaed Hasan Piker and Medea Benjamin over March 2026 Cuba trip
- Approximately 650 delegates from 120 organizations across 33 countries participated in the "Nuestra América Convoy"
- Investigation encompasses roughly 40 American citizens and 145 nonprofits with $1 billion in combined revenues
- Philanthropist Hari Singham has directed $278 million into nonprofit groups; CodePink received $1.33 million after his 2017 marriage to cofounder Jodie Evans
Federal authorities have subpoenaed political influencer Hasan Piker and CodePink cofounder Medea Benjamin over a March Cuba trip, investigating potential violations of U.S. sanctions laws involving 650 delegates from activist organizations.
The Treasury Department has issued subpoenas to two prominent activists—Hasan Piker, a political streamer with a massive following on Twitch, and Medea Benjamin, cofounder of the activist group CodePink—as part of a federal investigation into whether they violated U.S. sanctions laws during a trip to Cuba in March. The administrative subpoenas, formally called Requests for Information, were issued by the Office of Foreign Assets Control and seek financial, logistical, and communications records related to the journey.
Piker and Benjamin were among roughly 650 delegates from 120 organizations across 33 countries who participated in what organizers called the "Nuestra América Convoy," or "Our America Convoy." The delegation traveled to Cuba in mid-March, bringing supplies to the island's Communist Party. Both activists publicly documented their trip on social media—Piker posted a photo on Instagram on March 10 announcing his departure, and Benjamin was photographed in Havana wearing a Palestinian keffiyeh. Federal investigators are examining whether the financing, coordination, and delivery of goods to Cuba crossed legal lines under U.S. sanctions statutes, which broadly restrict financial transactions and the export of goods or services to the island with only narrow exceptions for journalism, humanitarian work, and educational programs.
The investigation extends far beyond these two figures. Federal authorities are scrutinizing as many as 40 American citizens who joined foreign nationals, including a Brazilian activist named Thiago Avila, in what officials describe as a global network of anti-U.S. Marxists and communists. The probe encompasses approximately 145 U.S. nonprofits and activist groups with combined revenues of roughly $1 billion. Among those under investigation is Isra Hirsi, daughter of Representative Ilhan Omar of Minnesota, with investigators examining whether Omar may have funded her daughter's travel. The investigation also targets CodePink's DC Coordinator, Olivia DiNucci, a former Division I basketball player from Emerson College. Additionally, Jodie Evans, CodePink's other cofounder and wife of philanthropist Hari Singham, is being investigated for her role in organizing the trip. Singham has directed $278 million into nonprofit groups over nearly a decade, with CodePink receiving $1.33 million after his 2017 marriage to Evans.
The subpoenas represent what federal officials characterize as a broader effort to counter what they view as malign foreign influence operations inside the United States. The Trump administration has framed the investigation as part of a wider dragnet targeting what it describes as a far-left activist network that has spent years defending communist regimes while presenting its work as humanitarian aid and anti-war organizing. The organizations involved in coordinating the convoy—including the Venceremos Brigade and People's Forum, described as a hub for communist causes in New York City—have drawn particular scrutiny. The Democratic Socialists of America, a U.S. nonprofit that promotes Piker as a headline member, was also involved in organizing the delegation.
Piker, one of the most influential political streamers on the platform, has built a substantial online following through Marxist commentary and anti-American rhetoric. He has faced repeated public backlash for inflammatory statements, including past remarks that "America deserved 9/11," which he later characterized as poorly phrased. More recently, critics including Representative Ritchie Torres, a Democrat from New York, have accused him of amplifying antisemitic rhetoric following October 7, though Piker has denied antisemitism and said his criticism targets Israel rather than Jewish people. On a recent livestream, Piker dismissed a Justice Department indictment of Cuban leader Raúl Castro as a "sham" with "no legal standing."
Benjamin has made her reputation as an activist known for staging media spectacles at Congressional hearings, defense industry conferences, and government officials' homes, presenting herself as anti-war while, according to federal characterizations, promoting messages that denounce the United States and uplift communist and authoritarian regimes including Iran, China, and Cuba. She was photographed on the trip with her partner and fellow activist Tighe Barry.
The legal stakes are significant. The subpoenas could determine whether prosecutors pursue criminal charges under the International Emergency Economic Powers Act, known as IEEPA, or whether the matter remains a civil enforcement issue handled by the Treasury Department. The Office of Foreign Assets Control can impose civil penalties under a "strict liability" standard, meaning the government does not need to prove intent. Criminal prosecution, by contrast, typically requires prosecutors to demonstrate willful violation of the law, often through evidence of concealment or knowing participation in prohibited transactions. Legal experts have indicated that the subpoenas represent a serious escalation and could be a precursor to criminal charges.
The investigation reflects growing concern among federal authorities and lawmakers about whether foreign actors and aligned organizations are attempting to shape American political discourse, mobilize activists, and normalize rhetoric that could encourage violence or undermine U.S. national security interests. The delegation stayed at a hotel the State Department has designated as directly tied to Cuba's communist government, which is listed as a state sponsor of terrorism. Additional subpoenas are expected as the investigation continues.
Notable Quotes
Piker dismissed a Justice Department indictment of Cuban leader Raúl Castro as a 'sham' with 'no legal standing,' characterizing Trump as acting like a 'playground bully.'— Hasan Piker, on a recent livestream
The Hearth Conversation Another angle on the story
Why would the federal government pursue this now, specifically? What changed?
The investigation is framed as part of a broader effort to counter what officials call malign foreign influence operations. The timing coincides with the Trump administration's stated focus on what it sees as far-left activist networks defending communist regimes. The scale—40 citizens, 145 nonprofits, $1 billion in revenues—suggests this has been building for a while.
What's the actual legal violation they're investigating? Is it just that these people went to Cuba?
Not exactly. U.S. law restricts financial transactions and the export of goods to Cuba with narrow exceptions. The investigation is examining whether the convoy's financing, coordination, and delivery of supplies crossed those lines. It's about whether money changed hands, whether goods were delivered, whether there were contacts with Cuban government entities. Simply traveling isn't illegal; the legal question is what happened during and around the trip.
What's the difference between what the Treasury Department can do and what the Justice Department can do?
Treasury can impose civil penalties without proving intent—what's called strict liability. Justice would need to prove willful violation, often through evidence of concealment or knowing participation. Criminal charges are a higher bar. These subpoenas are essentially the government gathering information to decide which path to take.
Who is Hari Singham and why does he matter so much to this story?
He's a philanthropist who married CodePink cofounder Jodie Evans in 2017 and has since directed $278 million into nonprofit groups. CodePink alone received $1.33 million from him. He's central because his funding network—the organizations he supports—coordinated much of the convoy. Following the money reveals the infrastructure.
Is there any chance this is just political targeting?
That's a question people will reasonably ask. The investigation is being conducted by Treasury, State, and Justice departments and is framed as countering foreign influence. Whether it's proportionate or selective is something observers will debate. What's clear is the scale is enormous—145 nonprofits, $1 billion in revenues—and the focus is on organizations that support communist and anti-U.S. causes.
What happens next?
The subpoenas are requests for information. Once the government reviews financial records, communications, and logistics, prosecutors will decide whether to pursue criminal charges under the International Emergency Economic Powers Act or keep it as a civil matter. More subpoenas are expected. This is early in the process.