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Hasan Piker Rattled as Feds Probe Cuba Trip, Crockett Piles On

Federal investigators are examining whether far-left streamer Hasan Piker violated U.S. sanctions during a March trip to Cuba, with authorities subpoenaing communications about his stay.

Stefanos Banos
Stefanos Banos Staff Writer
MAY 25, 2026 AT 9:24 PM

A prominent far-left online influencer is facing mounting pressure from federal investigators over a controversial trip to Cuba earlier this year, as New York Post reports, with officials examining whether the visit violated longstanding United States sanctions against the Communist regime.

Hasan Piker, a 34-year-old political streamer, acknowledged the federal probe during a broadcast on Sunday, telling his audience that authorities are pursuing him over his March travel to the island nation located just 90 miles from Florida’s coast. The investigation has clearly unsettled the influencer, who admitted to viewers the situation was troubling.

According to New York Post, federal authorities have issued subpoenas to both Piker and Medea Benjamin, co-founder of the activist organization CodePink, requesting communications and documentation related to their Cuban journey. The Treasury Department’s Office of Foreign Assets Control is leading the investigation into more than three dozen individuals.

The federal scrutiny stems from online reports suggesting that Piker and his fellow travelers lodged at a hotel in Havana that faces US sanctions. Trip participants have disputed these allegations.

Piker and Benjamin joined the “Nuestra America Convoy,” a gathering of several hundred left-wing activists from Europe and North America who traveled to Cuba ostensibly to deliver humanitarian assistance. The convoy was organized in response to the Trump administration’s hardline approach toward the Cuban government, which faces severe energy shortages following the January detention of Venezuelan President Nicolas Maduro.

Treasury Department regulations governing Cuban assets impose strict limitations on transactions with the Communist nation, particularly concerning hotels and businesses with direct government connections. Limited exceptions exist for humanitarian work, journalism, educational activities, and similar purposes.

The Treasury Department declined to provide comment when NewsFire inquired about the ongoing investigation.

Adding to Piker’s difficulties, Democratic Representative Jasmine Crockett of Texas shared a video mocking the streamer for his refusal to support Vice President Kamala Harris during the 2024 election cycle.

Benjamin defended the trip on social media Sunday, claiming the Trump administration was investigating individuals for providing medicine to Cuban children while supporting policies that restrict access to food, fuel, and medical supplies for those same children.

Piker, whose uncle is Cenk Uygur of The Young Turks, has built a reputation for controversial commentary. His past statements include declaring in 2019 that America deserved the September 11 attacks, and characterizing the October 7, 2023 Hamas assault as a direct result of Israeli policy. He has also praised the “brave mujahideen” who wounded Representative Dan Crenshaw of Texas during his military deployment in Afghanistan, and made inflammatory remarks about Senator Rick Scott of Florida.

With information from New York Post

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Stefanos Banos
Stefanos Banos

Stefanos Banos was born in Piraeus and is an editor at NewsFire.GR, specializing in political analysis and international relations. He graduated from the Department of Communication and Media at the University of Bremen in Germany, where he also completed his Master of Arts in Communication and Media Studies. Married to Zoi, he is a proud father of three boys.

A prominent far-left online influencer is facing mounting pressure from federal investigators over a controversial trip to Cuba earlier this year, as New York Post reports, with officials examining whether the visit violated longstanding United States sanctions against the Communist regime.

Hasan Piker, a 34-year-old political streamer, acknowledged the federal probe during a broadcast on Sunday, telling his audience that authorities are pursuing him over his March travel to the island nation located just 90 miles from Florida’s coast. The investigation has clearly unsettled the influencer, who admitted to viewers the situation was troubling.

According to New York Post, federal authorities have issued subpoenas to both Piker and Medea Benjamin, co-founder of the activist organization CodePink, requesting communications and documentation related to their Cuban journey. The Treasury Department’s Office of Foreign Assets Control is leading the investigation into more than three dozen individuals.

The federal scrutiny stems from online reports suggesting that Piker and his fellow travelers lodged at a hotel in Havana that faces US sanctions. Trip participants have disputed these allegations.

Piker and Benjamin joined the “Nuestra America Convoy,” a gathering of several hundred left-wing activists from Europe and North America who traveled to Cuba ostensibly to deliver humanitarian assistance. The convoy was organized in response to the Trump administration’s hardline approach toward the Cuban government, which faces severe energy shortages following the January detention of Venezuelan President Nicolas Maduro.

Treasury Department regulations governing Cuban assets impose strict limitations on transactions with the Communist nation, particularly concerning hotels and businesses with direct government connections. Limited exceptions exist for humanitarian work, journalism, educational activities, and similar purposes.

The Treasury Department declined to provide comment when NewsFire inquired about the ongoing investigation.

Adding to Piker’s difficulties, Democratic Representative Jasmine Crockett of Texas shared a video mocking the streamer for his refusal to support Vice President Kamala Harris during the 2024 election cycle.

Benjamin defended the trip on social media Sunday, claiming the Trump administration was investigating individuals for providing medicine to Cuban children while supporting policies that restrict access to food, fuel, and medical supplies for those same children.

Piker, whose uncle is Cenk Uygur of The Young Turks, has built a reputation for controversial commentary. His past statements include declaring in 2019 that America deserved the September 11 attacks, and characterizing the October 7, 2023 Hamas assault as a direct result of Israeli policy. He has also praised the “brave mujahideen” who wounded Representative Dan Crenshaw of Texas during his military deployment in Afghanistan, and made inflammatory remarks about Senator Rick Scott of Florida.

With information from New York Post