The Michael Knowles Show

Ep. 1937 - Bizarre Stunt: Libs Fly To Cuba To Cry About Trump

Date: March 23, 2026
Host: Michael Knowles (The Daily Wire)

Episode Overview

In this episode, Michael Knowles dives into what he considers an absurd political spectacle: American left-wing activists, notably Code Pink and streamer Hasan Piker, flying to Cuba for a so-called "humanitarian" trip aimed at critiquing U.S. policy and supporting the Cuban regime. Knowles scrutinizes the underlying motives, highlighting what he sees as hypocrisy and foreign manipulation. The show also covers Lindsey Graham’s provocative Iran war rhetoric, a rare moment of agreement with AOC over gambling, and Trump’s nuanced posture on military strategy in the Middle East.

Key Discussion Points & Insights

1. The “Humanitarian” Trip to Cuba: Virtue Signaling or Subversion?

[01:00 - 14:30]

• Background: Activist group Code Pink and progressive streamer Hasan Piker organize a charter flight to Cuba, bringing medicine and supplies while publicly condemning the Trump administration’s policies towards Cuba.
• Michael Knowles’ Critique:
  • Claims this trip props up the Cuban regime rather than aiding Cubans, stating, “These radical leftists wanna go down, not to buoy the spirits of the Cuban people, but to prop up the Cuban regime against the United States.” [02:25]
  • Notes the irony of environmental activists now lobbying for more oil to be sent to Cuba, stating, “Left wing activists have spent the last 25 years telling us we need to stop burning oil... Americans, Cuban communists should definitely burn oil.” [04:55]
• Code Pink’s Motives:
  Knowles alleges Code Pink operates as a Chinese disinformation initiative, referencing its funding from Neville Roy Singham, allegedly linked to the Chinese Communist Party:
  “They’ll switch their ideology, depending on the needs of their backers, which is China.” [06:20]
• Hasan Piker’s Perspective:
  Piker frames the trip as an effort to reveal “the regular experiences for regular Cuban folks” amidst a “communication blackout.” [08:53]
• Knowles’ Rebuttal:
  • Criticizes the elitism and disconnect: “Hasan Piker was broadcasting from a five-star hotel... Cubans can’t get electricity, can’t get fuel, can’t get food... Hasan Piker... stays at a five-star hotel.” [10:44]
  • Disproves Piker’s claim that US law requires Americans to stay in hotels:
    “Actually, the American government prohibits it. What Hasan Piker is doing is illegal, and I hope he's prosecuted by the United States.” [13:13]

Notable Quotes

• “Tourism is the lifeline for the Cuban economy. The government has very limited resources... even the five-star hotels are not like this [luxurious]... but regardless, in comparison to the situation on the island, it’s like prosperity.” – Hasan Piker [12:14]
• “Hasan Piker... dripping in my Cartier glasses, sipping my little espresso. You don’t understand, I had to stay in the five-star hotel. The American government made me.” – Michael Knowles [13:13]

2. Firsthand Experiences in Cuba

[14:00 - 20:00]

• Personal Anecdotes:
  Knowles recounts his own trip to Cuba:
  • He describes stark inequalities; hotels and pools are off-limits to Cubans, highlighting the performative side of tourism-centric humanitarianism.
  • “The hotels, they’re not for Cubans. Cubans aren’t allowed to go into the hotels. Only tourists are allowed to go into the hotels.” [14:30]
  • Discusses systemic poverty: “The average income in Cuba is $180 to $200 per year — not per month, per year.” [15:47]
• The Irony of Blackouts:
  During a widespread power outage, only the hotel where activists and journalists stayed had electricity, underscoring both hypocrisy and regime priorities.

3. Progressive Contradictions & Media Reactions

[20:00 - 22:00]

• Greta Thunberg’s shifting activism from anti-oil to pro-oil for Cuba is flagged as the latest in “issue-flopping.”
• Journalist Taylor Lorenz’s call for visitors to always wear masks in Cuba is lampooned:
  “It’s like every left wing neurosis, every left wing vice and neurosis is just being thrown into a blender in this Cuba smoothie.” [21:45]

4. Surprise Agreement with AOC on Gambling

[22:30 - 26:00]

• AOC’s Statement: She criticizes pervasive gambling, arguing it’s harmful for society, exploiting addiction and debt.
• Knowles’ Reaction:
  “AOC’s right. This is sad that AOC is right, but she’s right. Pervasive gambling is bad. We should not be betting on everything.” [24:17]
• Policy Context:
  • Traces history of gambling restrictions in the U.S., establishing that widespread legalization is a recent development.
  • Frames the issue as a traditional conservative/libertarian divide.

Notable Quote

• “Let all who have ears to hear, let them hear. AOC’s right... We should not be betting on everything.” – Michael Knowles [24:30]

5. The Columbus Statue Reinstalled at the White House

[26:40 - 31:00]

• Context: A Columbus statue, toppled during the 2020 protests, is re-erected by Trump on White House grounds.
• Symbolism & Defense:
  • Knowles argues for defending historical figures, including controversial ones, against erasure.
  • “This is the unbroken story of America.... If all you want to do is defend the founding generation... you have to go back further, defend not only George Washington, but defend all of the statues... Defend Columbus.” [30:36]
  • Stresses the power of monuments: “Statues tell us who we revere. Monuments tell us what we are. Cult and culture come from the same root word.” [31:04]

6. Escalation in Iran: Lindsey Graham & the Kharg Island Gambit

[35:40 - 38:00]

• Graham’s Proposal:
  • Senator Lindsey Graham compares the potential military operation to take Iran’s Kharg Island to the WWII Battle of Iwo Jima, expressing confidence in U.S. Marines.
  • “We did Iwo Jima. We can do this. My money is always on the Marines.” – Lindsey Graham [36:26]
• Knowles’ Caution:
  • Strongly challenges the analogy, warning the American public won’t support large casualties for an obscure objective:
    “He’s saying, ‘Oh, look, we took Iwo Jima, we can take this one.’ Whoa, whoa, whoa... That’s supposed to make me feel better?” [37:37]
  • Emphasizes that even in a best-case scenario, Americans won’t tolerate a war with thousands of casualties over a distant island.

7. Trump’s Strategic Posture on Iran

[43:33 - 47:00]

• Trump’s Response:
  In response to questions about his Iran strategy, Trump jokes:
  “You know, I may have a plan or I may not. But how would I ever say that to a reporter?... I can’t tell you that.” [43:33]
  • Knowles interprets this as calculated ambiguity, preventing adversaries from anticipating U.S. moves.
• Official Objectives:
  Trump’s True Social post lists objectives: degrade Iran’s missile and military industrial capacity, bar it from nuclear weapons, protect U.S. allies, and keep open the Strait of Hormuz, not regime change.
  • “Trump does not say that [regime change]; he is a politician who loves the practical, who loves the real.”
  • Warns: “If you allow them to close the Strait, and the US backs off, you’ll be in a worse position than before...” [48:09]

Notable Quotes & Memorable Moments

• “These radical leftists... not to buoy the spirits of the Cuban people, but to prop up the Cuban regime against the United States.” – Michael Knowles [02:25]
• “Hasan Piker cannot complete an English sentence in a way that is grammatically appropriate... how does this guy have an audience?” – Michael Knowles [08:53]
• “[AOC:] ‘Pervasive gambling is not good for society. It turns life into a casino, traps people in addiction and debt.’” [23:13]
• “We did Iwo Jima. We can do this. My money is always on the Marines.” – Lindsey Graham [36:26]
• “That’s supposed to make me feel better that this is going to be like Iwo Jima?” – Michael Knowles [37:37]
• “You know, I may have a plan or I may not. But how would I ever say that to a reporter?” – President Trump [43:33]

Key Timestamps (MM:SS)

• 01:00 – Show segment begins: Cuba trip context
• 04:55 – Irony of leftists demanding oil for Cuba
• 08:53 – Hasan Piker’s trip details; Knowles critiques
• 12:14 – Piker’s hotel explanation; Knowles’ legal correction
• 14:30 – Knowles’ personal Cuba experience
• 15:47 – Economic hardships in Cuba
• 20:00 – Greta Thunberg’s shifting activism
• 21:45 – Taylor Lorenz’s call for masks in Cuba mocked
• 23:13 – AOC’s statement on gambling
• 24:17 – 24:30 – Knowles’ rare agreement with AOC
• 26:40 – Columbus statue reinstalled
• 30:36 – Defense of monuments and American heritage
• 35:40 – Lindsey Graham: “We did Iwo Jima” analogy
• 37:37 – Knowles: Americans won’t back high-casualty war
• 43:33 – President Trump: “I may have a plan or I may not”
• 47:00+ – Trump outlines practical Iran objectives

Tone and Closing

The tone is highly critical, sarcastic, and combative, particularly toward progressive activists and political hypocrisy on the left. Knowles employs humor and mockery as he unpacks what he frames as the self-defeating inconsistencies of progressive politics, while supporting traditional conservative stances and Trump-era policies.

For listeners seeking a conservative critique of leftist activism and foreign policy, this episode offers in-depth commentary, spicy rhetoric, and an unusual but genuine moment of bipartisan agreement.