Anti-ICE Chaos Erupts, Hasan Piker Faces Federal Probe, Cuba Probe Expands | 5/26/26 FIRST LOOK

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1:17Hey, everybody. I'm Dave Rubin, and this is First Look. It's Tuesday, May 26th, 2026. We've got a packed show for you today. Anti-ice protesters clash with federal agents outside a Newark detention center as Democrat Governor Mickey Sherrill is denied entry. The Trump administration launches a federal investigation into Hassan Piker, Medea Benjamin, and far-left activists tied to aid convoys sent to communist Cuba. Let's dive in. We start in New Jersey, where anti-ICE protests erupted into chaos Monday outside the Delaney Hall Detention Center in Newark, as activists physically confronted federal agents and Democrat Governor Mickey Sherrill attempted to gain access to the facility, only to be turned away.

2:06And honestly, this entire situation has become a perfect snapshot of America's immigration divide under the Trump administration. According to reports, protesters formed a human chain around the detention center. Demonstrators blocked entrances and exits. Activists sat in the roadway trying to stop vehicle traffic, and some protesters were seen carrying Antifa flags. Video from the scene showed screaming matches between demonstrators and ICE agents as tensions escalated throughout the day. Crowds chanted, No more ICE! Others yelled, free them all. And at one point, protesters reportedly threw water at federal agents, while officers detained several demonstrators near the entrance.

2:53Now, this all unfolded while New Jersey Governor Mickey Sherrill attempted to enter Delaney Hall, a request federal officials denied. Footage circulating online showed Sherrill standing outside a locked razor wire gate, while protesters chanted, let Sherrill in. After being refused access, Cheryl accused ICE and DHS of hiding conditions inside the facility. She said, My request for access to Delaney Hall was formally denied this morning, raising serious questions about what they are trying to hide from public view. Cheryl also reiterated her opposition to private detention centers and called for Delaney Hall to eventually be shut down entirely.

3:36But the Department of Homeland Security blasted the governor's visit as a political stunt. A DHS spokesperson told Fox News that visitation had already been suspended because riots and unrest outside the facility created security concerns. Officials said roughly 125 agitators surrounded the building over the weekend, forming barricades and blocking access points. And honestly, one major detail getting lost in a lot of the media coverage is who exactly is being held at this facility. Back in February 2025, DHS officials stated Delaney Hall housed murderers, terror suspects, child rapists, and MS-13 gang members.

4:22That's important context when protesters are outside chanting, free them all. Now, inside the detention center, nearly 300 detainees have reportedly launched a hunger and labor strike while claiming conditions are inhumane. In a public letter, detainees acknowledged they entered the United States illegally, but said they now feel kidnapped. The letter accused ICE of poor food conditions, medical neglect, psychological abuse, and inadequate treatment. But DHS pushed back hard on those allegations. Federal officials say detainees receive three meals a day, clean water, bedding and clothing, toiletries and showers, phone access to family and attorneys, and meals reviewed by certified dieticians.

5:12A DHS spokesperson added, ICE has higher detention standards than most U.S. prisons that hold actual U.S. citizens. Now, politically, this story highlights a growing split in America. On one side, the Trump administration says immigration laws matter, detention facilities are necessary, and criminal illegal aliens must be removed from the country. On the other, progressive activists increasingly portray nearly all immigration enforcement as morally illegitimate. And as the 2026 midterms approach, immigration enforcement is once again becoming one of the defining issues in American politics. Now to another major story involving the far left, and this one is quickly escalating into a serious federal probe.

6:01According to reports, federal investigators have now subpoenaed left-wing streamer Hassan Piker and radical activist Medea Benjamin over their involvement in aid convoys sent to communist Cuba earlier this year. The investigation is being led by the Treasury Department's Office of Foreign Assets Control, or OFAC, which enforces U.S. sanctions laws. And according to Fox News, more than 40 Americans are now under scrutiny over possible violations tied to the so-called Nuestra America Convoy. The flotilla delivered roughly 20 tons of humanitarian aid to Cuba back in March. Now, supporters of the convoy claim this was simply humanitarian work, meant to help struggling Cubans suffering through shortages of food, fuel, medicine, and basic supplies.

6:52But investigators are now examining whether activists violated federal sanctions law by financing prohibited activity, coordinating unauthorized travel, or improperly exporting goods and services to Cuba. And one of the most controversial figures involved is Hassan Piker. Piker, a massive left-wing Twitch streamer and self-described democratic socialist, has built a career attacking capitalism, America, and US foreign policy. This is also the same Hasan Piker who famously said on stream, America deserved 9-11, and has previously made comments suggesting capitalists should be dragged through the streets and killed.

7:35After returning from Cuba, Piker openly praised the communist regime and criticized U.S. sanctions policy. Meanwhile, Medea Benjamin, co-founder of the radical anti-war group Code Pink, has long been one of the most controversial activist figures on the American left. Benjamin has made multiple trips to Gaza, met directly with Hamas officials, posed for photos with former Hamas leader Ismail Hania and repeatedly defended regimes openly hostile to the United States. Now, Code Pink insists it broke no laws. The organization claims the Cuba trip qualified under humanitarian exemptions allowed under U.S.

8:18law. In a statement, the group said, we did nothing wrong during our March 2026 trip to Cuba. Benjamin herself framed the investigation as political persecution. She wrote on X, the Trump administration is investigating people for bringing medicine to Cuban children. And honestly, this is where the broader political issue comes into focus. The Trump administration increasingly believes that parts of the activist left are functioning less like humanitarian organizations and more like ideological defenders of authoritarian anti-American regimes. Because this isn't just about generic anti-war activism anymore.

9:00These are people openly defending communist governments, undermining American sanctions, attacking U.S. foreign policy, and in some cases, praising regimes tied to terrorism and hostile foreign powers. And this investigation comes as tensions involving Cuba continue escalating rapidly. The Trump administration has reimposed major sanctions, tightened restrictions on Havana, increased pressure campaigns against the Cuban regime, and repeatedly warned about Cuba's growing ties to China, Russia, and Iran. Meanwhile, Republicans are increasingly framing Cuba not simply as a failed communist state, but as a hostile regime operating just 90 miles off the Florida coast.

9:46Now, whether criminal charges eventually come from these subpoenas remains unclear, but one thing is obvious. The Trump administration is no longer treating these activist networks as harmless protest groups. Federal investigators appear to believe something much larger may be happening beneath the surface. And that's your first look this Tuesday. Quick recap. Anti-ICE protesters clash with federal agents outside a Newark detention center while Governor Mickey Sherrill is denied entry. Hassan Piker and Medea Benjamin are subpoenaed as part of a federal investigation into Cuba aid convoys and possible sanctions violations.

10:28We'll keep following all of it. I'm Dave Rubin. Thanks for starting your day with First Look. See you tomorrow.