Far-left political streamer Hasan Piker appeared visibly shaken this weekend after reports surfaced that federal authorities are investigating whether his March trip to Cuba violated U.S. sanctions law.
Speaking candidly during a livestream Sunday, Piker acknowledged the seriousness of the situation while venting frustration over the federal probe.
“This is not great,” Piker told his audience. “I mean it’s bulls—, but still not great that they’re after your boy. They’re up my ass.”
At another point during the stream, after viewers joked about him needing legal help, Piker sarcastically responded, “Yeah, free me. Free me. I can’t believe I’m saying that. But I’m about to be seemingly made an example of.”
The controversy exploded after Fox News reported that the Treasury Department had issued subpoenas connected to Piker’s Cuba trip earlier this year. The investigation reportedly also includes Medea Benjamin, the co-founder of the far-left activist organization CodePink.
According to reports, Piker and Benjamin were among more than three dozen people being examined by the Treasury Department’s Office of Foreign Assets Control, the federal agency responsible for enforcing U.S. sanctions.
The investigation appears tied to allegations that members of the group may have stayed at a U.S.-sanctioned hotel in Havana during the trip. Participants have denied those claims.
Federal officials have not publicly detailed the exact scope of the investigation, and the Treasury Department declined to comment when asked about the matter.
Under the Cuban Assets Control Regulations, Americans face significant restrictions when conducting financial transactions involving certain Cuban businesses, particularly entities connected to the communist government or military apparatus. There are exemptions for journalism, educational activity, and humanitarian efforts, but violations can still trigger serious federal scrutiny.
Piker traveled to Cuba as part of the “Nuestra America Convoy,” a large delegation of left-wing activists and socialists from North America and Europe. Organizers described the mission as a humanitarian effort aimed at delivering aid and protesting U.S. policy toward Cuba.
The trip took place amid escalating tensions between the Trump administration and the Cuban regime, particularly after renewed pressure campaigns targeting Cuba’s communist government and its relationship with Venezuela.
Benjamin lashed out publicly after news of the investigation broke.
“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,” she wrote on X.
The backlash against Piker online intensified further after Democratic Congresswoman Jasmine Crockett appeared to mock him over the investigation. Crockett reposted a video criticizing Piker for discouraging support for Kamala Harris during the 2024 election.
“That’s what you get for telling people to vote third party or not vote at all,” the video stated, prompting Crockett to respond with side-eye emojis.
The episode adds yet another controversy to Piker’s long history of inflammatory political commentary. The streamer, who is also the nephew of Young Turks founder Cenk Uygur, has repeatedly generated outrage over comments involving terrorism, foreign policy, and American politics.
In 2019, Piker faced enormous backlash after declaring that “America deserved 9/11.” Following the Hamas attacks against Israel on October 7, 2023, he argued the violence was a “direct consequence” of Israeli policy and suggested allegations involving Hamas atrocities would not fundamentally alter his view of the conflict.
He has also previously praised Afghan fighters who injured Congressman Dan Crenshaw during military service and made remarks about Senator Rick Scott that critics condemned as deeply inappropriate.
Now, however, Piker’s attention appears focused less on online political warfare and more on the possibility of a federal sanctions investigation becoming a very real legal problem.
