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 hear from OFAC, whether by administrative subpoena or by the softer letter the agency often uses instead, and why would a trip to Cuba trigger it?

OFAC Administrative Subpoena vs. Request for Information

The reporting in the Cuba matter is a useful illustration of a distinction that trips up even sophisticated people: an OFAC administrative subpoena and a “request for information” are not the same instrument, and which one shows up tells you a good deal about how serious your situation is.

The administrative subpoena is the heavier of the two. Lawyers who deal with OFAC call it a “602,” after 31 C.F.R. § 501.602, the regulation that gives the agency its power to demand records. The provision is broad on its face: “Every person is required to furnish under oath … complete information relative to any transaction” subject to the sanctions rules, “regardless of whether such transaction is effected pursuant to license or otherwise.” A 602 is written as a command. It directs you to produce documents, and for a U.S. person it is compulsory. Stonewalling it becomes its own problem, separate from whatever OFAC was investigating in the first place.

A request for information, or RFI, is the softer cousin. It reads less like an order than an inquiry: OFAC “requests that you answer the following questions” as part of an enforcement review. The agency reaches for an RFI in two situations. The first is when the recipient is a non-U.S. person. OFAC’s own practice reflects a quiet recognition that, whatever § 501.602 says about “every person,” it cannot actually force someone outside U.S. jurisdiction to answer, so it asks rather than commands. The second is when a matter involving a U.S. person sits, at least for the moment, on the less serious end of the spectrum. The instrument OFAC chooses is itself a signal.

There is a trap worth flagging, especially for non-U.S. recipients. The fact that OFAC cannot compel your answer does not make a false or misleading answer safe. Respond untruthfully and you can hand the government a brand-new violation, a false-statements charge under 18 U.S.C. § 1001, stacked on top of whatever it was already examining. A truthful, carefully scoped response and a sloppy or evasive one are worlds apart.

Which did the convoy participants get? We cannot say for certain, but the public signals point toward requests for information, at least for many of them. Both Piker and Benjamin have said no subpoena was served on them. And the broader inquiry reportedly sweeps in hundreds of delegates from dozens of countries, many of them non-U.S. persons OFAC has no authority to subpoena in the first place. For a U.S. person, drawing an RFI rather than a subpoena usually suggests OFAC is still in an early, fact-gathering posture rather than building toward a penalty. That is not a reason to relax. It is a reason to get the first response right.

Whichever form the demand takes, it is not a finding that a violation occurred, and it is not a charge. It is a request for records and answers, full stop. OFAC’s underlying authority traces to the International Emergency Economic Powers Act (IEEPA) and the regulations behind each sanctions program. In the Cuba matter, the reporting says the demands reach for financial and logistical records and the communications tied to the trip. Recipients generally have a deadline, and how they meet it 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 a subpoena 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 OFAC inquiry 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 a subpoena or 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.

There is also a conspicuous gap in who has drawn scrutiny and who has not. Around the time the convoy traveled to Cuba, the YouTuber Nick Shirley reportedly visited the island and stayed at a hotel on the Cuba Restricted List, close to the conduct OFAC is now said to be examining. There has been no public report of a subpoena, an RFI, or any investigation touching him. A contrast like that is hard to square with evenhanded enforcement, and it raises a fair question: is the Cuba inquiry really about the Cuban Assets Control Regulations, or is it selective enforcement by the Trump administration aimed at its political critics?

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 a demand from OFAC turns up in your inbox, a 602 subpoena or a request for information. 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 subpoena or request for information mean I am being charged with a crime? No. Both are investigative tools. They tell 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.

What is the difference between an OFAC administrative subpoena and a request for information? An administrative subpoena, often called a “602” after 31 C.F.R. § 501.602, is a compulsory demand for records that OFAC uses mainly with U.S. persons. A request for information is a softer, non-compulsory inquiry the agency tends to send to non-U.S. persons it cannot force to respond, and to U.S. persons in matters that are, for now, less serious. Either way, an inaccurate or misleading response can create fresh legal exposure of its own.

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.