Federal officials have reportedly served subpoenas to political streamer Hasan Piker and CodePink cofounder Medea Benjamin as part of an investigation into trips to Cuba and possible violations of U.S. sanctions laws.
The inquiry is focused on whether U.S. organizations, activists and public figures helped finance, coordinate or deliver goods to Cuba in ways that may have violated federal restrictions.
The subpoenas were issued by the Treasury Department’s Office of Foreign Assets Control, which oversees U.S. sanctions programs. They seek financial, logistical and communications records connected to travel to Cuba earlier this year.
Piker and Benjamin reportedly traveled to Cuba in March with delegations connected to the “Nuestra América Convoy,” also known as the “Our America Convoy.” The group included activists, influencers and organizations that described the trip as a solidarity effort with the Cuban people.
TRENDING TODAY
Federal investigators are now examining whether any part of the trip involved prohibited transactions, contact with Cuban government-linked entities or support for organizations tied to the communist regime.
The investigation is part of a broader federal effort involving Treasury, State and Justice Department officials to examine foreign influence operations and U.S.-based activist networks with ties to authoritarian or hostile governments.
Officials are also reportedly reviewing whether activists stayed at hotels or used businesses restricted by the U.S. government because of ties to Cuba’s communist leadership.
U.S. sanctions law places broad limits on travel-related transactions and financial activity involving Cuba. Some exceptions exist for journalism, humanitarian work, education and activities meant to support the Cuban people, but investigators are looking at whether the March trip crossed legal lines.
The broader inquiry could involve as many as 40 American citizens who joined foreign nationals and activists during the convoy to Havana.
Legal experts say the subpoenas do not necessarily mean criminal charges will follow. The case could remain a civil sanctions matter handled by OFAC, or prosecutors could pursue criminal charges if they believe there was a willful violation of federal law.
Piker is one of the most prominent political streamers in the United States and has built a large online audience around left-wing and anti-establishment commentary.
Benjamin, a longtime anti-war activist and cofounder of CodePink, has frequently disrupted congressional hearings and public events while criticizing U.S. foreign policy.
Neither Piker nor Benjamin responded to requests for comment in the report.
The investigation comes as the Trump administration increases pressure on Cuba’s government and expands scrutiny of U.S.-based groups accused of supporting or defending communist regimes abroad.
🚨 The Treasury Department has subpoenaed Hasan Piker and Medea Benjamin as part of a probe into possible Cuba sanctions violations.
Between Hasan’s “wads of cash” and Medea describing thousands of pounds of goods sent to Cuba, it is not hard to see why Treasury has questions. pic.twitter.com/WRhC5PMDmw
— Stu Smith (@thestustustudio) May 24, 2026
