Bezos Torches Mamdani, Raul Castro Bombshell, Unexpected Trump Endorsement | 5/21/26 FIRST LOOK

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1:17Hey, everybody. I'm Dave Rubin, and this is First Look. It's Thursday, May 21st, 2026. We've got a packed show for you today. Former Cuban dictator Raul Castro is indicted on murder and terrorism-related charges tied to the killing of four Americans. Jeff Bezos torches New York Mayor Zoran Mamdani for targeting billionaire Ken Griffin in a bizarre class war video stunt. President Trump throws his support behind Spencer Pratt's insurgent run for mayor of Los Angeles. as frustration with Karen Bass continues growing. Let's dive in. We start with major breaking news out of Florida, and honestly, a historic moment for the Cuban-American community.

2:01Former Cuban President Raul Castro has now been formally indicted by a federal grand jury on charges including murder, conspiracy to kill U.S. nationals, and destruction of aircraft. The charges stem from the infamous 1996 shootdown of two civilian planes operated by the Miami-based humanitarian group, Brothers to the Rescue. And for many Cuban exiles, this is something they've waited decades to see. The indictment was unsealed Wednesday by Acting Attorney General Todd Blanche during a major announcement in Miami. According to prosecutors, four Americans, Carlos Costa, Armando Alejandre Jr., Mario de la Pena, and Pablo Morales, were flying unarmed humanitarian missions over international waters when Cuban military aircraft fired missiles at their planes and killed them.

2:57Blanche described the victims as civilians trying to help people fleeing communist oppression across the Florida Straits. He said, they were unarmed civilians and were flying humanitarian missions for the rescue and protection of people fleeing oppression. Then he added, nations and their leaders cannot be permitted to target Americans, kill them, and not face accountability. Now, prosecutors allege Castro personally participated in the conspiracy that led to the attack, and several Florida lawmakers made it very clear Wednesday that they believe Raul Castro directly gave the order to shoot the planes down.

3:38Congressman Carlos Jimenez said Castro actually boasted that he was the one that gave the order. Now, politically, this announcement absolutely electrified South Florida's Cuban-American community. The press conference became almost emotional at times. Florida Attorney General James Uthmeyer received thunderous applause after declaring, there can be no future for a free Cuba so long as the Castros and their criminal gang of thugs remain in power. Then he hinted something even bigger could still be coming. Uthmaier told the crowd, get ready, there's more to come. That line immediately fueled speculation that the Trump administration may be preparing additional pressure campaigns targeting the Cuban regime.

4:25Now remember, for decades, Cuban exile families have viewed the Brothers to the Rescue shootdown as one of the clearest examples of communist brutality in the Western Hemisphere. Congresswoman Maria Elvira Salazar called the indictment historic, and Congressman Byron Donalds described the pilots as humanitarians helping Cubans escape tyranny. He said people were swimming across the Florida Strait, and the brothers to the rescue were going out on their own to help people get to our shores. President Trump also weighed in Wednesday and praised the indictment directly. Trump said a lot of people have suffered very big, very, very, at levels that few people would understand.

5:12He added that Cuban Americans, whose families were destroyed under the Castro regime, had waited decades for accountability. And Trump suggested Cuba itself is beginning to weaken under economic pressure. He said, the place is falling apart. They've really lost control of Cuba. Now, legally speaking, this indictment may never result in Castro's standing trial in the United States. But symbolically and politically, this is massive. Because for the first time, the U.S. government is formally treating the actions of Cuba's communist leadership not just as political hostility, but as criminal acts against Americans.

5:54And in South Florida, many exiles see this as something even bigger, the beginning of the end for the Castro legacy itself. Now to New York City, where even Jeff Bezos is now publicly warning that socialist-style class warfare politics are pushing major investment and business leaders out of America's largest city. During a CNBC interview Wednesday, Bezos sharply criticized Mayor Zoran Mamdani for filming a viral video outside billionaire Ken Griffin's Manhattan penthouse while celebrating a new luxury property tax proposal. And Bezos didn't hold back. He said Ken Griffin isn't a villain. Then he added, he hasn't hurt anybody.

6:36He's not hurting New York. In fact, quite the opposite. Now the controversy centers around Mamdani's so-called Pied-a-Teir tax, a proposal targeting luxury second homes worth more than$5 million. Last month, Momdani filmed a highly theatrical video outside Griffin's record-breaking$238 million penthouse in Midtown Manhattan, while directly calling him out by name. The mayor framed the proposal as a strike against ultra-wealthy absentee homeowners, but critics blasted the stunt as creepy, vindictive, and openly anti-business, and now Bezos is joining that criticism. Importantly, Bezos actually said he's fine with having a policy debate about taxes.

7:24But what he objected to was the public demonization of successful people. Bezos said policy discussions don't require finger pointing. Now this comes after Ken Griffin himself already warned that Mamdani's rhetoric and policies are helping drive investment away from New York and toward places like Florida. Griffin even suggested Citadel could reconsider a massive$6 billion Park Avenue development project because of the city's political climate. And honestly, this is becoming a broader pattern. More and more business leaders are openly saying New York is hostile towards success. Taxes are spiraling out of control.

8:07Regulations are suffocating growth. and city leadership increasingly treats wealth creation like a moral crime. But Bezos didn't stop there. He also blasted Mamdani's education spending priorities. The mayor is pouring a record$43 billion into New York public schools, despite declining enrollment, mediocre test scores, and already massive per-student spending. Bezos pointed out New York spends roughly$44 ,000 per student, which is about 30 % higher than cities like Chicago, Los Angeles, and Boston. Yet outcomes continue deteriorating. Bezos also hammered New York's housing policies, arguing skyrocketing rents are largely the result of excessive government intervention.

8:59He called it a skills issue. And honestly, what makes this politically fascinating is that Bezos is not exactly some conservative MAGA firebrand. This is Jeff Bezos, the owner of Amazon, the Washington Post, one of the richest men on earth. And even he is now publicly warning that radical left-wing governance is becoming economically destructive. That tells you how far things have shifted. And finally, one of the strangest and most entertaining political stories in the country just got even bigger. President Trump is now openly rooting for former reality TV star Spencer Pratt in the Los Angeles mayoral race.

9:41Speaking to reporters Wednesday before departing for the Coast Guard Academy commencement ceremony in Connecticut, Trump was asked whether he sees similarities between himself and Pratt, another former reality TV personality entering politics. Trump responded, I'd like to see him do well. He's a character. Then Trump added, I hear he's a big MAGA person. Now, Pratt's mayoral campaign started off as something many people dismissed as a joke, but increasingly, it's becoming a real political movement fueled by frustration with the collapse of Los Angeles under Karen Bass. According to recent polling, Pratt is now running in second place within single digits of Bass and currently ahead of progressive councilwoman Nithya Raman.

10:25And his rise has largely been fueled by viral social media videos, massive online engagement, and a surprisingly straightforward message about restoring basic public order in Los Angeles. In one recent interview, Pratt declared, no more nakedness, no more drug use, no more robbing, no more dog abuse. And honestly, the reason that message is resonating is because people in Los Angeles are exhausted. Residents have watched homeless encampments explode. crime worsen, open drug use become normalized, businesses flee, and city leadership seem completely disconnected from ordinary taxpayers. Meanwhile, Karen Bass has faced heavy criticism over her handling of last year's devastating wildfires, rising homelessness, public safety failures, and increasingly bizarre policy priorities.

11:20In fact, during an interview last week, Bass said one of her priorities was providing taxpayer-funded dentures to meth addicts. And when asked why the city wasn't doing more to address rampant meth use itself, Bass largely dodged the question. That exchange immediately went viral and became symbolic of what critics see as a city government more focused on managing decline than restoring order. Now, Trump also raised concerns Wednesday about election integrity in California. He warned that you have a really rigged vote in California, specifically criticizing universal mail-in voting, ballot harvesting, and delayed vote counting systems.

12:03Trump said, very hard to win because the elections are very dishonest. Now, whether Spencer Pratt can actually pull this off remains to be seen. But politically, something very interesting is happening here. Los Angeles voters, even many moderates and independents, increasingly seem willing to consider completely unconventional candidates because confidence in the city's leadership has collapsed so badly. And honestly, when a former reality TV star running on Stop the Chaos starts polling competitively in Los Angeles, that probably tells you everything you need to know about the current state of the city.

12:40And that's your first look this Thursday. Quick recap, former Cuban dictator Raul Castro is indicted over the killing of four Americans in the 1996 Brothers to the Rescue shoot-down. Jeff Bezos blasts Zoran Mamdani for targeting billionaire Ken Griffin in a class war video stunt. And President Trump throws his support behind Spencer Pratt's insurgent run for mayor of Los Angeles. We'll keep following all of it. I'm Dave Rubin. Thanks for starting your day with First Look. See you tomorrow.

13:38Dave Rubin:We'll see you next time. Edens Plaza, and Will Mett. Wayfair, every style, every home.