Federal investigators have issued subpoenas to Marxist political influencer Hasan Piker and CodePink cofounder Medea Benjamin as part of an ongoing investigation into potential violations of U.S. sanctions laws related to Cuba. The administrative subpoenas, sent by the Treasury Department’s Office of Foreign Assets Control, seek detailed information about trips both activists took to the communist-ruled island nation in March. The inquiry examines whether American organizations and leaders illegally supported Cuba’s government through financing, coordination, or delivery of goods, including contact with Cuban officials or state entities.
The investigation targets participants in the “Nuestra América Convoy” or “Our America Convoy,” a caravan organized by a global network of communist sympathizers, activists, and influencers who transported supplies to Cuba’s ruling Communist Party. Approximately 650 delegates from 33 countries and 120 organizations participated in the March convoy, including members of the Democratic Socialists of America, which promotes Piker as a prominent figure. Federal authorities are examining whether the trip’s financing, logistics, and delivery of goods crossed legal boundaries under U.S. sanctions law.
Treasury Department requests financial records and communications
The administrative subpoenas, officially called “Requests for Information,” demand financial records, logistical details, and communications related to the March journey. Both Piker and Benjamin have publicly discussed their participation in the convoy on social media platforms. On March 10, Piker posted on Instagram with the message “I’M GOING TO CUBA,” while photos from the trip show Benjamin wearing a Palestinian kefiyyeh alongside Piker in Havana. The investigation represents a serious escalation by the Trump administration against far-left nonprofit networks that have defended communist regimes while presenting their activities as humanitarian aid and anti-war organizing.
Officials from the Treasury, State, and Justice departments are coordinating efforts to curb malign foreign influence operations within the United States. The scrutiny reflects growing concern among federal authorities about foreign actors attempting to shape American political discourse, mobilize activists, and potentially encourage violence or undermine national security interests. The Office of Foreign Assets Control is investigating whether activists violated U.S. sanctions through unlicensed travel-related transactions and export of goods or services to Cuba, which has limited exceptions for journalism, humanitarian projects, and educational programs.
Investigation extends to 40 American citizens and global activist network
The federal dragnet includes as many as 40 American citizens who joined foreign nationals in the convoy, including Brazilian activist Thiago Avila, who belongs to a global network of anti-U.S. Marxists, communists, and socialists. Additional subpoenas are expected as the investigation expands. Officials are examining 145 U.S. nonprofits and activist groups with $1 billion in collective revenues as part of a wider influence campaign potentially linked to Cuba’s communist regime and other foreign actors. Delegation members reportedly stayed at a hotel on the U.S. State Department’s “Cuba Restricted List,” which identifies businesses directly tied to the communist government.
Among those under scrutiny is Isra Hirsi, daughter of Representative Ilhan Omar. Investigators are examining whether Omar may have funded her daughter’s travel to Cuba. The Office of Foreign Assets Control is also investigating CodePink’s Washington coordinator, Olivia DiNucci, a former Division I basketball player who joined a convoy led by Brazilian activist Avila. DiNucci has gained attention for disrupting Congressional hearings and defense industry conferences with loud theatrics. Representatives for Piker, Benjamin, and Omar did not respond to requests for comment.
Cuban Asset Control Regulations impose strict transaction limits
U.S. law imposes broad restrictions on financial transactions involving Cuba through the Cuban Asset Control Regulations, administered by the Office of Foreign Assets Control. The rules generally prohibit unlicensed travel-related transactions and export of goods or services to Cuba. The Office of Foreign Assets Control can impose civil penalties under a strict liability standard, meaning the government does not need to prove intent. However, the Justice Department must demonstrate willful violation of the law in criminal cases, typically through evidence of concealment, evasion, or knowing participation in prohibited transactions.
- Subpoenas seek financial records, logistical details, and communications about March Cuba trips.
- Investigation targets 40 American citizens who participated in Nuestra América Convoy.
- Federal authorities examining 145 U.S. nonprofits with $1 billion in collective revenues.
- Cuban Asset Control Regulations prohibit unlicensed transactions with Cuba.
- Office of Foreign Assets Control can impose civil penalties without proving intent.
Legal experts indicate the subpoenas could determine whether prosecutors pursue criminal charges under the International Emergency Economic Powers Act or whether the matter remains a civil enforcement issue. The investigation is part of broader efforts to examine activities tied to political violence, extremist movements, or acts classified as terrorism by the U.S. government. Cuba remains designated as a state sponsor of terrorism by the State Department.
Piker defends Cuba trip and criticizes Justice Department indictment
Piker, one of the most influential political streamers on Twitch, has built a massive online following with Marxist politics and anti-American commentary. During a livestream this week, he called the Justice Department’s indictment of Cuban leader Raúl Castro a “sham” with “no legal standing,” arguing the action creates a pretext for escalating U.S. pressure on the island. Piker suggested Trump is acting like a “playground bully” in dealing with Cuba. The streamer has faced criticism for past controversial statements, including saying “America deserved 9/11,” which he later characterized as poorly phrased.
Representative Ritchie Torres has accused Piker of amplifying antisemitic rhetoric following events of October 7, though Piker has denied antisemitism and stated his criticism targets Israel, not Jewish people. The influencer has also drawn backlash for comments about former Representative Dan Crenshaw, a Navy SEAL veteran who lost an eye in Afghanistan. In a recent livestream, Piker interviewed another influencer about various topics, defended Cuba’s communist leaders, and criticized chaos in America, calling the situation “terrifying.”
Organizations in convoy received millions from controversial donor
Organizations involved in the Nuestra América Convoy have received significant funding from Neville Roy Singham, who has pumped $278 million into nonprofit groups promoting pro-China, pro-Cuba, and anti-U.S. narratives since his February 2017 marriage to CodePink cofounder Jodie Evans. CodePink received $1.33 million from Singham after he married Evans, who is also being investigated for her role in the March trip. Organizations in the Singham network, including the Venceremos Brigade and People’s Forum in New York City, were leaders of the convoy that brought supplies to Cuba’s ruling party.
Benjamin has established herself as an activist who stages media spectacles at Congressional hearings, defense industry conferences, and homes of government officials. While branding herself as “anti-war,” her pattern of messages denounces the United States while uplifting communist and authoritarian regimes from Iran to China and Cuba. The investigation marks a significant challenge to nonprofit activist networks that have spent years defending communist governments while characterizing their work as humanitarian aid and solidarity with people oppressed by American imperialism.