Federal investigators have served subpoenas to left-wing streamer Hasan Piker and CodePink co-founder Medea Benjamin as part of a widening probe into whether a March aid convoy to Cuba violated U.S. sanctions law. The Treasury Department's Office of Foreign Assets Control is now scrutinizing more than 40 American citizens who participated in the trip, the New York Post reported.
The subpoenas demand production of financial, logistical, and communications records tied to the so-called "Nuestra America Convoy," which delivered roughly 20 tons of supplies to Havana. The question OFAC wants answered is straightforward: did the participants finance, coordinate, or deliver goods to a designated state sponsor of terrorism without the required federal license?
For Piker, 34, and Benjamin, 73, the legal exposure is real. The Cuban Assets Control Regulations prohibit U.S. citizens from unlicensed travel-related transactions and from exporting goods or services to Cuba. Limited exceptions exist for humanitarian projects, journalism, educational programs, and certain activities meant to support the Cuban people, but claiming an exception and proving one are two different things.
Fox News reported that the March delegation included approximately 650 delegates from 33 countries and 120 organizations. The convoy delivered its cargo directly to the Communist Party of Cuba, a detail that complicates any humanitarian-exception defense. Bringing medicine to children is one thing. Handing supplies to a ruling communist party apparatus is another.
Piker, a self-described democratic socialist who built his audience on Twitch, reportedly sang praises of the communist regime following the trip. Benjamin, a veteran activist who co-founded the anti-war feminist group CodePink, has a long record of engagement with U.S.-sanctioned governments and designated terrorist organizations.
Between 2009 and 2012, Benjamin made at least seven trips to Gaza, where she met with Hamas officials including the group's then-leader Ismail Haniyeh. Publicly posted photos documented those meetings. She has faced sustained criticism over her alleged ties to Hamas and Iran, a history that adds context to the federal government's interest in her latest overseas venture.
OFAC does not issue administrative subpoenas casually. The office enforces economic and trade sanctions, and its investigations can lead to civil penalties, criminal referrals, or both. The subpoenas served on Piker and Benjamin require them to turn over a broad set of records: financial documents, logistical planning materials, and communications related to the Cuba trip.
No formal charges have been filed. The investigation remains in its administrative phase. But the breadth of the probe, more than 40 Americans under scrutiny, signals that OFAC views the convoy as more than a casual goodwill mission.
The legal landscape around Cuba travel has tightened. The Trump administration moved last year to blockade the island, and just last week the Justice Department issued an indictment against former Cuban President Raúl Castro. The details of that indictment have not been made public, but the timing underscores a broader enforcement posture toward Havana and those who deal with its government.
Both Benjamin and CodePink have pushed back hard. CodePink released a statement insisting the group did nothing wrong:
"We did nothing wrong during our March 2026 trip to Cuba. On the contrary, we acted as moral US citizens trying to bring some relief to a population being deliberately starved by the cruel policies of our own government."
Benjamin took to X to frame the investigation as a political attack. Her post cast the probe as an assault on compassion rather than an enforcement of sanctions law:
"The Trump administration is investigating people for bringing medicine to Cuban children while defending policies that deprive those same children of food, fuel, and basic medical supplies. If loving the Cuban people is a crime, then millions around the world are guilty too."
Notice what neither statement addresses: the legal requirements of the Cuban Assets Control Regulations, whether the convoy obtained the necessary OFAC licenses, or why supplies were delivered to the Communist Party of Cuba rather than through a licensed humanitarian channel. The rhetoric is about morality. The subpoenas are about law.
CodePink has claimed that its members, aside from Benjamin personally, have yet to be served subpoenas. The organization did not clarify whether Benjamin was served in her personal capacity, her organizational role, or both. That distinction could matter as the investigation unfolds.
The identities of the other 40-plus Americans under scrutiny remain unknown. So does the precise scope of what OFAC believes went wrong. The investigation could conclude with administrative penalties, criminal referrals, or nothing at all. But the subpoenas themselves are a concrete step, not a political gesture.
The Trump administration and Republican allies have also ramped up warnings that the United States may take military action against Cuba. Those threats were not detailed in available reporting, but they form part of the backdrop against which this investigation is playing out.
Benjamin's biography reads like a tour of regimes and organizations hostile to the United States. Seven documented trips to Gaza. Meetings with Hamas leadership. Now a convoy delivering goods directly to the Communist Party of a designated state sponsor of terrorism. At some point, a pattern of engagement with America's adversaries stops looking like humanitarian impulse and starts looking like something else entirely.
Piker, for his part, built a media brand on radical left-wing politics and used that platform to promote the Cuba trip. Whether his involvement amounted to more than cheerleading is something the financial and communications records may clarify.
The humanitarian-exception defense is available under the law. But exceptions are narrow, require proper licensing, and demand that aid reach the Cuban people, not the Cuban state. If OFAC determines that 20 tons of supplies went to the Communist Party without authorization, the "we were just helping children" defense will collide with the actual text of federal sanctions law.
The subjects and their allies will frame this investigation as political retaliation. That framing is predictable and convenient. It is also beside the point. The Cuban Assets Control Regulations exist regardless of who occupies the White House. OFAC's enforcement authority does not depend on the political identity of the target. And sanctions against a designated state sponsor of terrorism are not optional guidelines that activists get to waive because they believe their cause is just.
Americans who want to send aid to suffering populations have legal channels to do so. Those channels exist precisely so that humanitarian intent does not become a loophole for propping up hostile regimes. When activists bypass those channels and then cry persecution when the government asks questions, they are not defending humanitarianism. They are demanding impunity.
The law does not care how many followers you have or how righteous you feel. It asks a simpler question: did you get the license, or didn't you?