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

Summary

Podcast Summary: The Rubin Report

Episode: Bezos Torches Mamdani, Raul Castro Bombshell, Unexpected Trump Endorsement | 5/21/26 FIRST LOOK
Date: May 21, 2026
Host: Dave Rubin

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Episode Overview

In this episode, Dave Rubin delivers fast-moving commentary and analysis on three major political stories:

1. The unprecedented indictment of former Cuban President Raul Castro by a US federal grand jury.
2. Jeff Bezos’s public rebuke of New York Mayor Zoran Mamdani over class warfare policies and anti-business rhetoric.
3. President Trump’s surprise endorsement of Spencer Pratt’s insurgent mayoral campaign in Los Angeles.

Rubin explores the significance of these stories for politics, business, and society, capturing the escalating frustration with political leadership in major US cities and the shifting tone of national debate.

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Segment 1: Raul Castro Indicted – A Watershed for Cuban Americans

[00:34 – 04:30]

• News Recap:
  Former Cuban dictator Raul Castro has been indicted in the United States for murder, conspiracy, and destruction of aircraft, relating to the 1996 shootdown by Cuban forces of two civilian planes from Miami’s “Brothers to the Rescue” group. Four Americans were killed.

• Context and Reactions:

  • The announcement was emotionally charged, especially among South Florida’s Cuban American community, who have campaigned for justice for decades.
  • The indictment was unsealed by Acting Attorney General Todd Blanche, who described the victims as "civilians trying to help people fleeing communist oppression across the Florida Straits."
  • Blanche:

    “Nations and their leaders cannot be permitted to target Americans, kill them and not face accountability.” (03:00)

  • Congressman Carlos Jimenez claimed Castro “boasted that he was the one that gave the order.”
  • Florida Attorney General James Uthmeyer’s statement:

    “There can be no future for a free Cuba so long as the Castros and their criminal gang of thugs remain in power. Get ready. There’s more to come.” (04:08)

  • Congresswoman Maria Elvira Salazar and Congressman Byron Donalds hailed the indictment as “historic,” calling the victims “humanitarians helping Cubans escape tyranny.”
  • President Trump chimed in:

    “A lot of people have suffered very big, very, very at levels that few people would understand.” (04:50)
    “The place is falling apart. They’ve really lost control of Cuba.” (05:05)

• Analysis by Dave Rubin:
  While Castro will likely never face US trial, the move is hugely symbolic, formally treating Cuba's actions as criminal attacks on Americans. Many exiles see it as "the beginning of the end for the Castro legacy."

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Segment 2: Jeff Bezos vs. New York’s Class Warfare Politics

[06:00 – 09:20]

• Controversy Over Luxury Property Tax:
  New York Mayor Zoran Mamdani proposed a “pied-à-terre tax” targeting luxury second homes above $5 million. He filmed a viral video outside billionaire Ken Griffin’s Midtown penthouse, directly denouncing Griffin by name.

• Business Backlash:

  • Jeff Bezos, in a CNBC interview, slammed Mamdani’s stunt:

    “Ken Griffin isn’t a villain. He hasn’t hurt anybody. He’s not hurting New York. In fact, quite the opposite. … Policy discussions don’t require finger pointing.” (06:45, 07:10)

  • Critics called the mayor’s approach “creepy, vindictive and openly anti-business.”
  • Ken Griffin has threatened to reconsider Citadel’s $6 billion Manhattan project due to the city's "hostile" climate towards wealth.

• Broader Impact and Bezos’s Critique:

  • Bezos argued that demonizing business leaders is driving investment away from New York to states like Florida.
  • He pointed out the city’s soaring education budget:

    “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." (08:27)

  • On housing, Bezos blamed “excessive government intervention” for skyrocketing rents, calling the crisis "a skills issue."
  • Rubin notes the irony:
    Even "the owner of Amazon and The Washington Post... is now publicly warning that radical left wing governance is becoming economically destructive. That tells you how far things have shifted."

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Segment 3: Trump Endorses Spencer Pratt’s Los Angeles Mayoral Run

[09:21 – 11:54]

• Trump’s Comments and The Crossover with Pop Culture:

  • Trump was asked if he sees himself in Spencer Pratt (ex-reality star, now political candidate).

    "I'd like to see him do well. He's a character. I hear he's a big MAGA person now." (09:44)

• The Rise of Pratt’s Campaign:

  • Initially viewed as a joke, Pratt’s campaign now polls in second place, ahead of progressive Nithya Raman and within single digits of incumbent Karen Bass.
  • Pratt’s social media-driven campaign focuses on restoring public order:

    “No more nakedness, no more drug use, no more robbing, no more dog abuse.” (10:30)

  • The platform’s straightforwardness strikes a chord with frustrated Angelenos tired of crime, homelessness, and official inaction.

• Critique of Karen Bass:

  • Bass has faced blowback for her wildfire response, homeless crisis management, and other “bizarre policy priorities.”
  • Rubin highlights a viral moment:
    Bass recently prioritized "taxpayer funded dentures to meth addicts" but sidestepped questions on curbing meth use itself.

• Election Integrity Issues:

  • Trump raised concerns over California’s mail-in voting and ballot harvesting:

    "Very hard to win because the elections are very dishonest." (11:32)

• Analysis:
  The unexpected competitive showing of a reality star with a “Stop the Chaos” campaign, Rubin suggests, says everything about voter disenchantment in LA today.

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Notable Quotes & Moments

• On Raul Castro Indictment:
  “There can be no future for a free Cuba so long as the Castros and their criminal gang of thugs remain in power.” – James Uthmeyer (04:08)
  “The place is falling apart. They’ve really lost control of Cuba.” – Donald Trump (05:05)

• On Class Warfare in NYC:
  “Ken Griffin isn’t a villain… Policy discussions don’t require finger pointing.” – Jeff Bezos (06:45, 07:10)
  “New York spends roughly $44,000 per student… Yet outcomes continue deteriorating.” – Jeff Bezos (08:27)

• On LA Politics:
  “No more nakedness, no more drug use, no more robbing, no more dog abuse.” – Spencer Pratt (10:30)
  “You have a really rigged vote in California.” – Donald Trump (11:32)

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Key Timestamps

• 00:34 – Raul Castro’s indictment announcement
• 04:08 – Florida Attorney General’s rallying message
• 05:05 – Trump on Cuba’s decline
• 06:45–07:10 – Bezos on Mamdani’s anti-billionaire stunt
• 08:27 – Bezos on NYC education spending
• 09:44 – Trump on Spencer Pratt’s mayoral bid
• 10:30 – Pratt’s “no more chaos” pitch
• 11:32 – Trump critiques California’s election system

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Conclusion

This “First Look” episode captures a moment of seismic political realignment and growing popular rejection of ineffective or antagonistic leadership in America’s largest cities. Rubin’s take is brisk, provocative, and grounded in the voices driving today’s headlines, from emboldened Cuban exiles to embattled business leaders and insurgent political outsiders.

Transcript

[A]

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[B]

Hey everybody. I'm Dave Rubin and this is First Look. It's Thursday, May 21, 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. Former Cuban President Raul Castro has now been formally indicted by a federal grand jury on charges including murder, conspiracy to kill US 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 Della Pena and Pablo Morales, were flying unarmed humanitarian missions over international waters when Cuban military aircraft fired missiles at their planes and killed them. Blanche 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. Congressman 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. Uthmeyer 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 that targeting the Cuban regime Now 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. He added that Cuban Americans whose families were destroyed under the Castro regime and 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 standing trial in the United States. But symbolically and politically, this is massive because for the first time, the US Government is formally treating the actions of of Cuba's communist leadership not just as political hostility, but as criminal acts against Americans. And 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. He's not hurting New York. In fact, quite the opposite. The now the controversy centers around Mamdani's so called pied a terre tax, a proposal targeting luxury second homes worth more than $5 million. Last month, Mamdani 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, but 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, regulations 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. He 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. Speaking 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 and currently ahead of progressive Councilwoman Nithya Raman. And 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. In 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. Trump 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. And 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 shootdown. 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.

[C]

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