OFAC Subpoenas Hasan Piker and Medea Benjamin Over a Cuba Trip

The Office of Foreign Assets Control (OFAC), the Treasury Department agency that runs U.S. sanctions programs, has reportedly served administrative subpoenas on a group of American activists who traveled to Cuba in March 2026. A Fox News Digital report published on May 23, 2026, names the Twitch streamer Hasan Piker and CodePink co-founder Medea Benjamin among the recipients, and says the inquiry reaches as many as 40 U.S. citizens who joined the “Nuestra América Convoy,” or “Our America Convoy.” Piker said on a livestream over the weekend that no subpoena had reached him personally and that he had learned of the investigation from the press.

How this particular matter ends is anyone’s guess. But it surfaces a question that comes up far more often than the headlines suggest: what does it actually mean to receive an OFAC subpoena, and why would a trip to Cuba trigger one?

What Is an OFAC Administrative Subpoena (Request for Information)?

When clients ask me what an OFAC “Request for Information,” or RFI, actually is, I tell them it is the government’s way of saying: show us your records. It is a formal demand for documents, and OFAC sends it while it is still figuring out what happened. Nobody has decided yet whether you broke the law or whether any penalty is coming. In the Cuba matter, Fox News reported that the subpoenas reach for financial and logistical records and the communications tied to the trip.

An RFI is not a finding that a violation occurred, and it is not a charge. It is a request for information, full stop. OFAC’s authority to demand records comes from the International Emergency Economic Powers Act (IEEPA) and the regulations implementing each sanctions program. Recipients generally must respond by a stated deadline. How they respond matters enormously. The production tells OFAC how to read the conduct, and more often than not it determines whether the file gets closed, resolved with a civil settlement, or handed up the chain.

The first few weeks tend to set the tone. A sloppy or overbroad production can hand the government facts that make lawful activity look like a violation; ignoring the request entirely creates a separate problem of its own. This is the point where experienced administrative subpoena counsel earns its keep, by reading the scope of the request narrowly, asserting any privileges that apply, and putting the facts in front of OFAC accurately.

Why a Trip to Cuba Draws OFAC Scrutiny

Cuba sits under one of the few comprehensive U.S. sanctions programs, which OFAC administers through the Cuban Assets Control Regulations (CACR), codified at 31 C.F.R. Part 515. It is also designated a State Sponsor of Terrorism. Stack those two facts on top of each other and the default flips: financial transactions that touch the island are presumed off-limits unless something specifically allows them. That is why getting on a plane to Havana is not like getting on a plane to almost anywhere else.

Travel to Cuba Is Not Tourism

Tourist travel to Cuba is flatly prohibited. A U.S. person may go only if the trip fits one of twelve authorized travel categories set out in the regulations, such as journalistic activity, professional research, educational activities, and “support for the Cuban people.” If your trip fits a category, you travel under a general license and never have to file an application with anyone. Here is the part people miss: you still have to genuinely satisfy that category’s conditions, and you have to keep the records that prove you did.

The humanitarian and journalistic framing of the March convoy lines up with several of these categories. Participants have described delivering medical supplies to pediatric hospitals and conducting interviews and reporting on the island. Did each traveler’s conduct actually fit an authorized category, and did the money and logistics around the trip stay inside the lines? Those are the facts an OFAC investigation goes looking for.

Exporting Goods and the “Support for the Cuban People” Category

The CACR reaches past travel itself to restrict exports of goods and services to Cuba and the financing of activity on the island. Donations of certain humanitarian items, and exports meant to support the Cuban people, can be authorized. But whether they are authorized depends on the details: what the goods are, who actually ends up with them, and how the whole thing was paid for. Hand a box of supplies to a private family and you are in one place legally. Route that same support to a Cuban government entity and you are in another. According to the reporting, investigators are looking at how the convoy was financed, how it was coordinated on the ground, and how the goods were delivered, along with whether any participant had prohibited contact with Cuban government personnel.

The Cuba Restricted List

The State Department maintains a Cuba Restricted List of hotels, businesses, and other entities tied to the Cuban government and its military and intelligence services. U.S. persons generally cannot transact directly with anything on it. Book a room at a listed hotel and you may have made a prohibited transaction even if your underlying travel category was otherwise fine. Whether transactions like that occurred is exactly the sort of detail an RFI is built to draw out.

Civil or Criminal? IEEPA, Strict Liability, and Willfulness

In any OFAC matter, one question tends to overshadow the rest: does it stay a civil enforcement issue handled by OFAC, or become a criminal case referred to the Department of Justice? The two tracks run on very different standards.

• Civil enforcement. OFAC can impose civil penalties on a strict liability basis. Here is what that means in plain terms: the government does not have to show you intended to break the law, and it does not even have to show you knew the conduct was off-limits. The violation can stand on its own. Your intent and your compliance efforts still matter, but they go to how large the penalty is, not to whether you are liable in the first place.
• Criminal prosecution. A criminal case under IEEPA demands far more. Prosecutors generally have to prove that the defendant acted willfully, meaning with knowledge that the conduct was unlawful. That is why prosecutors lean on evidence of cover-up. Hiding the conduct, structuring around the rules, or knowingly running prohibited transactions is the kind of thing that turns a file criminal.

The records OFAC collects through an RFI frequently decide which of those tracks a matter follows. Plenty of people treat the investigative stage as a warm-up. It is usually where the case is actually won or lost.

What the Investigation Reportedly Involves

According to the reporting, the Cuba inquiry is one piece of a wider effort spanning the Treasury, State, and Justice Departments and aimed at a network of nonprofits and activists. CodePink co-founder Jodie Evans and the organization’s DC coordinator are reportedly among those under scrutiny, and investigators are said to be tracing the funding behind the convoy and the roughly 650 delegates from dozens of countries who took part. More subpoenas are reportedly on the way.

For most readers, the politics of the convoy matter less than the legal machinery it puts on display. The same Cuban Assets Control Regulations, the same twelve travel categories, the same Cuba Restricted List, and the same civil-versus-criminal analysis would apply to a relief nonprofit, a freelance journalist, a church planning a mission trip, or a company weighing humanitarian exports. The rules were always there. A case like this one just puts them on the front page.

What to Do If You Receive an OFAC Subpoena

So an RFI from OFAC turns up in your inbox. What now? A few things I tell clients in that first conversation.

First, do not sit on it. These requests carry deadlines, and silence almost always makes the underlying problem harder to fix than it had to be.

Second, freeze your records the moment you learn an investigation exists. Deleting or changing relevant documents at that point is its own offense, and a serious one, entirely apart from whatever OFAC was originally asking about.

Read the request carefully before you hand anything over. The wording defines exactly what you owe. Give too little and you look evasive; give too much and you may be feeding the government facts it never asked for and could use against you.

When you do respond, stick to the facts. Lay them out accurately and completely, but resist the urge to characterize your own conduct or concede legal points. Save the legal conclusions for your lawyer.

And get that lawyer involved early, because the first response tends to set the trajectory of everything that follows, including whether the matter stays civil or turns criminal.

Frequently Asked Questions

Does receiving an OFAC RFI mean I am being charged with a crime? No. A Request for Information is an investigative tool. It tells you OFAC is gathering facts, not that a violation has been established or that charges have been filed. Plenty of these matters close with no penalty at all.

Is humanitarian travel to Cuba legal? It can be. Certain humanitarian, journalistic, educational, and “support for the Cuban people” activities run under general licenses, but each carries specific conditions and recordkeeping obligations. Whether a particular trip qualifies comes down to the facts, including how it was financed and who the travelers dealt with on the island.

Can OFAC penalize me even if I did not know I was breaking the law? Yes. OFAC’s civil penalties run on a strict liability standard, so a lack of intent is no defense to liability, though it weighs heavily on the size of any penalty. The criminal side of IEEPA works the other way around: there, the government has to prove willfulness.

About Sanctions Law Center

An OFAC administrative subpoena or Request for Information is unforgiving of guesswork. The early, careful decisions are the ones that pay off. The OFAC attorneys at Sanctions Law Center work with individuals, nonprofits, journalists, and businesses on the full arc of an inquiry: responding to OFAC, sizing up their exposure under programs like the Cuban Assets Control Regulations, and figuring out where the line falls between a civil enforcement matter and a criminal referral.

Our Washington, DC practice handles OFAC sanctions exclusively, including OFAC enforcement and investigations and proactive compliance counseling for organizations whose work brings them into contact with sanctioned jurisdictions. If you have received an OFAC subpoena, or you are planning activity that may implicate U.S. sanctions, contact us to schedule a consultation.