Risks of LARPing as a Cuban Humanitarian

Introduction

Federal investigators issued subpoenas to Twitch streamer Hasan Piker and CodePink cofounder Medea Benjamin, as part of a larger probe into the March “Nuestra América Convoy”  to Cuba with 40 other U.S. activists.^[1] The Treasury’s Office of Foreign Assets Control (OFAC) is trying to determine whether the trip, which delivered medical aid to Cuba under a banner of solidarity, violated the U.S. embargo on Cuba. 

Checking in to Hotel California 

Around 40 Americans joined dozens of international activists to sail supplies to Cuba and visit hospitals, part of a “Nuestra América Convoy” organized by leftist NGOs. U.S. authorities suspect that convoy participants may have violated the U.S. Cuba embargo by coordinating with Cuban government entities or by staying in state-linked hotels.

Treasury investigators are particularly checking if convoys booked rooms at hotels on the State Department’s 2025 Cuba Restricted List, a blacklist of firms tied to Cuba’s government. U.S. law generally bans unlicensed transactions with Cuban entities, subject to only narrow exceptions such as permitted journalism, humanitarian aid, or educational exchanges. Though one would reasonably conclude Piker’s trip was for humanitarian aid, he could still be found liable for allegedly staying at a hotel on Cuba’s Prohibited Accommodations List.^[2] Section 708 of the OFAC website’s section on Cuban Sanctions leaves an exception to what defines a humanitarian visit, reading - “...exclude from the authorization lodging, paying for lodging, or making any reservation for or on behalf of a third party to lodge, at any property in Cuba on the Cuba Prohibited Accommodations List to the extent prohibited by § 515.210.“

Legal experts who spoke with Fox News, who broke this story, note the process could remain a civil OFAC enforcement case or escalate to a criminal IEEPA (International Emergency Economic Powers Act) prosecution, depending on the information gathered.^[3] Under IEEPA, willful sanctions evasion can result in fines up to $1 million and 20 years in prison per violation.

The Piker case is part of a recent broader crackdown on alleged foreign influence. Fox News and press wires say investigators have identified dozens more Americans who joined Cuba solidarity convoys led by a wealthy pro-communist network. The Treasury, Justice, and State departments are inspecting whether radical nonprofit groups funneled political activism under the guise of aid. The subpoena on Piker and Benjamin is described by officials as “part of a wider dragnet” to curb extremist or foreign-directed campaigns that exploit social media. 

Piker and Benjamin deny any wrongdoing. Both have publicly framed the trip as genuine humanitarian relief. Piker fired back on X/Twitter that the U.S. government would rather “try to criminalize delivering aid to a country we’ve starved” than target elite wrongdoers. He also posted defensively, “we stayed at the right hotel btw – the govt got duped by a f**ing viral Twitter post. I’m losing my mind.”. 

I was unable to find the Twitter post Hasan is referring to, but Fox News and others reported they were staying at Gran Hotel Bristol Habana Vieja.^[4] However, the New York Times reported on March 23rd that the group would be staying at Iberostar Marques de la Torre, later confirmed by Medea Benjamin to PolitiFact.^[5][6] It is important to note that neither of these hotels appears on the Cuba Restricted List.^[7]

Political and Legal Context

Since the Cold War, a rigorous embargo has barred most trade and tourist travel to Cuba from the US, citing human rights and national security concerns. Americans can’t just vacation there, as every trip must fit into a narrow category (education, cultural exchange, humanitarian aid, etc.). OFAC’s Cuban Assets Control Regulations explicitly forbid most financial transactions with the Cuban government or military-linked entities.^[8] Knowingly booking accommodations at a Cuban military-operated hotel can itself be a sanctions violation.

OFAC is looking for evidence of a crime, hence the requests for information. Potential civil penalties under U.S. law for an unlicensed sanctions breach can be up to $250,000 or twice the transaction value. If OFAC finds willful evasion, the matter could be referred for criminal prosecution under the IEEPA. 

In response, Piker immediately ramped up on stream, calling the subpoenas “intimidation tactics” and shifting the blame onto wealthy patron Neville Roy Singham (a businessman married to CodePink’s co-founder).^[9] He argued that federal authorities were selectively targeting activists who challenge U.S. foreign policy, while ignoring larger political and corporate corruption. Piker has also maintained that the convoy complied with applicable regulations and that media reports linking participants to prohibited accommodations are inaccurate.

Conclusion

The question now is whether this will quietly close or escalate. If investigators find paperwork lapses or sanction violations, Piker could face a civil penalty or be dragged into criminal court. A variety of people online have been making the claim that Piker may face larger charges or consequences as a result of Piker’s association with Code Pink and Progressive International, the organizers of the convoy.^[10]

The convoy was organized by Progressive International, working alongside other organizations like Code Pink. The official organizer for the convoy is David R.K. Adler, an American who works as Progressive International’s Co-General Coordinator.^[11] On the list of advisors for Progressive International appears Mariela Castro, daughter of former First Secretary Raul Castro.^[12] Mariela also made a speech, defending the Cuban regime and blasting the embargo.^[13] This, combined with Secretary of State Marco Rubio’s tough stance on the Cuban government, leads the poster to conclude that Hasan’s trip may not be found to be humanitarian at all, but an attempt “coordinated in part by the Cuban government to counteract the US strategic leverage being utilized against it." As phrased by one reddit user.

However, I was unable to find Mariela, or the National Center for Sex Education (CENESEX), the Cuban government entity of which she is director, or Progressive International, or David R.K. Adler on the U.S. Treasury OFAC sanctions lists, the Cuba Restricted List, or the SDN list.^[14][7][15] As far as one can reasonably tell, her interactions were perfectly legal and fell in line with sanctions against the Cuban government. If Rubio has taken notice of Piker in particular and singled him out, it is possible that there will be some way found around this, but there is no evidence to suggest that is the case. Piker was not the only one subpoenaed, but he was likely the most prominent. I’m not convinced that Piker has LARPed too close to the sun, but it is still too early to say. The subpoenas could unearth new information that paints Piker or Code Pink’s actions as criminal. Unfortunately for all of us, his LARP goes on, at least for now.

Another claim seems to be that Hasan admitted on stream that he coordinated with someone in the Cuban government to ensure internet access during his stay in Cuba, and thus admitted to "coordinating with the Cuban government" and violated sanctions or laws. ^[16]

Reading through the OFAC FAQ in regards to the Cuba sanctions, internet access and communications, even transactions, seem to be generally authorized.[17] "The general license ... authorizes ... certain services incident to the exchange of communications over the internet, services to support the exchange of communications..."

Most forms of internet communication are allowed, and the wording is deliberately broad. During the protests around 2021, the Biden-era administration sought to support Cuban communications and thus broadly authorized most social media transactions with the US.^[18]It is hard to imagine that, on this point alone, Hasan has committed a crime, as everything he claims to have done falls within these broad authorizations.

When asked for comment, the author of the linked Reddit post EightEight16 responded to me with the following, 

“The way the sanction laws are written, and the way in which the convoy was organized and executed, I would not begrudge anyone for coming out on one side or another in regards to the legal implications, perhaps as the laws were intended. What I would be willing to wager a great deal on is that the analysts looking in have almost certainly done a great deal more research than Hasan himself did before he struck boldly out to sea like his hero, Luffy. And if I were Hasan, I would be eyeing nervously the stacked volumes of One Piece with a worry that my own legal saga on the horizon might be nearly as long.”