The Dispatch Podcast — “How Far Will Trump Go in Cuba?”

Episode Date: March 31, 2026
Host: Jonah Goldberg (in for Steve Hayes)
Panelists: Kevin Williamson, Megan McArdle, Gil Guerra (Dispatch contributor, Latin America expert)
Main Theme: Exploration of Cuba’s spiraling crisis—focusing on blackouts, social unraveling, and whether the Trump administration will intervene for regime change. Also, a broader debate about U.S.-Cuba policy, the legacy of communism, and what comes next.

Episode Overview

This roundtable delivers a deep dive into Cuba's current crisis, particularly unprecedented rolling blackouts, their historical and geopolitical context, and the increasing possibility that the Trump administration will turn its “regime pressure” focus to the island. With Latin America expert Gil Guerra, the panel dissects the causes and consequences of Cuba’s energy collapse, debates the logic and risks of U.S. intervention, and discusses how different American political factions might respond if Cuba becomes the next flashpoint.

Key Discussion Points & Insights

1. Cuba’s Blackout Crisis – Origins and Impacts

[01:59–05:50] Gil Guerra Explainer

Grid Collapse: Cuba’s electricity grid, reliant on Soviet-era diesel plants, began failing after COVID-19 decimated tourism and Venezuela ceased subsidized oil. Recent blackouts—worse than anything since 2004—have now triggered mass protests.
Why It Matters: Cubans rely on electricity for stockpiling food; blackouts destroy food reserves and make everyday life unlivable. The regime’s model of pacifying citizens through basic provisions is breaking down.
Escalating Protests: Recent protests have eclipsed the 2021 July 11 demonstrations in duration, though harsh police crackdowns have stemmed intensity.
External Factors: Trump administration allowed Russian oil deliveries, temporarily alleviating shortages. The prevailing U.S. policy appears focused on creating conditions for Cuba’s collapse, gambling on internal regime change.
“There are a number of different factors that are unique to this time period and this moment in history that make it more complicated and also more volatile than U.S.-Cuba relations have ever been.” — Gil Guerra [05:48]

2. Should the U.S. Make Cuba a Foreign Policy Priority?

[05:50–10:21] Kevin Williamson’s Perspective

Questioning Priorities: Williamson explains U.S. focus on Cuba is largely inertia—a Cold War legacy—while other hemisphere crises (e.g., Haiti) are ignored.
Sanctions Skepticism: U.S. sanctions deliver suffering but don’t topple regimes; effective only as part of a larger strategy, which the U.S. never pursues.
Energy Lessons: The crisis highlights both Cuba's vulnerabilities and American energy strengths.
Quip: “I understand that Marco Rubio probably will be the viceroy of Cuba on top of his other 11 jobs…” — Kevin Williamson [09:33]

3. The Unique Dilemmas of Cuban Regime Change

[10:21–13:32] Megan McArdle Adds Nuance

Historical Context: U.S. efforts to topple Cuba once made strategic sense—Cuba hosted Soviet missiles, exported revolution and security services.
Now It’s Different: After ~60 years, few Cubans remember capitalism; rebuilding would resemble post-Soviet Russia more than Eastern Europe. The risk of chaos, refugees, and responsibility for “nation-building” weighs heavily.
“We could end up with a worse situation on our hands that we will be partly responsible for and we'll have to deal with. There will be floods of refugees.” — Megan McArdle [12:54]

4. The Hawkish Case for Intervention and Its Limits

[13:32–16:10] Gil Guerra Responds

Cuba Needs External Patrons: Historically, Cuba has only survived via external support—first the USSR, now Russia and China.
Chinese Influence: China has set up surveillance outposts in Cuba; ignoring Cuba lets adversaries stake out a base near the U.S.
Myth of Refugee Floods: Largest Cuban refugee waves (Mariel boatlift, etc.) came during periods of U.S. engagement, not confrontation.
Regional Dynamics: Cuba remains a hub for anti-U.S. agitation across Latin America.

5. Post-Communist “Muscle Memory”: The Challenge of Transition

[16:10–19:54] Robust Debate: Black Markets, Culture, and Diaspora

Muscle Memory? Goldberg argues Cuba’s robust black market might give it entrepreneurial “muscle memory” after a collapse; McArdle cautions that capitalism’s success rests on shared norms, reputation, and rule of law—not mere trade.
The Diaspora Variable: Many Cuban Americans and their descendants are well-integrated and may not “return” in droves if the regime falls, unlike other post-diaspora scenarios.

6. U.S. Legal Logic for Intervention: Pretexts and Triggers

[24:19–27:26] How Would Trump Justify It Legally?

Possible Playbook: The panel discusses how the Trump administration might manufacture a legal rationale—e.g., leveraging crackdowns on protests as a humanitarian pretext.
Succession Uncertainty: The looming death of Raul Castro (age 92) creates a potential power vacuum; “playboy” grandsons lack authority with the security services.
Rubio’s Political Stakes: Marco Rubio’s political future is intimately tied to Cuba policy; failure in Cuba could tarnish his standing.

“The plan seems to be to push Cuba towards some state of collapse or some state of an internal conflict that we will then have a justification for intervening on behalf of.”
— Gil Guerra [24:30]

7. Cuba as a Left-Wing Cultural Touchstone

[31:48–36:45] The “Romance” of Cuban Socialism

Still a Beacon? The left has long mythologized Cuba as a model (however illusory) of egalitarianism, health care, and artistic freedom.
Psychological Impact: Collapse of Cuban communism would be rationalized as “rapacious capitalism destroying a beautiful experiment” rather than a failure of socialism itself.
“Socialism at this point is sort of like a joke I once heard—a blues musician with 13 albums, and you keep buying each new one thinking, this is the one where it works out. But nope, he’s still having some trouble with his woman. And that’s where we are with socialism now.” — Megan McArdle [35:56]

8. Race, Inequality, and Who Is Left in Cuba

[37:18–41:19]

Broken Myths: Despite claims of racial enlightenment, real Cuban power structures remain disproportionately white and central; the most marginalized have little recourse and endure the worst hardships.
Mass Exodus: From 2020–2025, Cuba lost nearly 10% of its population—those left behind are typically young, old, or lack foreign ties (disproportionately Afro-Cuban).

“The way that Cuba has been portrayed as this paradise evolved past racism is completely false, and actually many of those prejudices are perhaps stronger in Cuba.”
— Gil Guerra [39:00]

9. Forecasting: Is Cuba Really ‘Next’?

[41:19–43:53] Foreign Policy Punditry

Depends on Iran? McArdle argues that Trump will only proceed if operations in Iran seem successful and politically advantageous.
Momentum Argument: If Iran “succeeds,” Trump may see an opening for a rapid Cuba intervention as a crowning foreign policy triumph. Others think that even a messy Iran operation could increase pressure for “success” elsewhere.
Difficulty: Cuba is, on paper, an easier target: closer, smaller, militarily weaker than Iran or Venezuela.

10. U.S. Political Reactions — Both Sides Predicted

[43:53–48:57] How Will the Left and Right Respond?

Progressive Reaction: Expected to frame Cuba’s collapse not as a failure of socialism, but as a victim of U.S. aggression.
On the Right: The MAGA base supports hardline moves in the hemisphere (Venezuela, Iran); Cuba may excite less actual passion. Few expect a MAGA revolt, even among nationalist critics.
Rubio’s Role: Rubio seen as the key driver, with Trump eager for a “historic” legacy.

Notable Quotes & Segments

“[In Cuba,] often you have serf wages except for the nobility, and the population left is mainly elderly, very young, or Afro-Cubans without family abroad. Cuba's reality is very different from its romanticized narrative.”
— Gil Guerra [41:00]

“We now have a really poisonous form of trolly, racist, anti-semitic youth politics that is increasingly, as the author says, institutionalized.”
— Jonah Goldberg, referencing a recent Dispatch article [54:44]

“If you're watching your news instead of reading your news, you're getting garbage. And if you are going to be relying on AI for doing anything, that's beyond the sort of stuff Megan's talking about... it's going to be useful in that kind of way. I also have never had an assistant, so it's the one thing in life I really want other than a private jet.”
— Kevin Williamson [64:32]

Timestamps for Important Segments

[01:59] — Gil Guerra’s overview of Cuba’s blackouts and economic collapse
[05:50] — Kevin Williamson on U.S. Cuba policy and the limits of sanctions
[11:12] — Megan McArdle on why Cuba regime change is more fraught than ever
[13:32] — “Cuba Hawk” arguments and the continuing regional security case
[16:10–19:54] — Diaspora dynamics, muscle memory debate, U.S. intervention risks
[24:19] — Legal pretexts for intervention, succession politics in Havana, Rubio's interests
[31:48] — The U.S. political romance with Cuban socialism and its cultural afterlife
[37:18] — Realities of race and power in Cuba post-blackout exodus
[41:19] — Predictions: Will Cuba truly be next after Iran/Venezuela?
[43:53] — Expected left/right U.S. reactions if Trump intervenes in Cuba
[52:08] — Panel’s Dispatch recommendations

Noteworthy Moments

Podcast banter: The hosts mock stereotypes about podcasting voices (Rick Astley reference) and fantasize about McDonald’s, KFCs opening in post-communist Cuba.
Mock “regime change TV movie casting”: Gil Guerra as “young Marco Rubio.” [13:51]
Socialist blues joke: “It’s like the blues musician with 13 albums—each time you think it’ll work out, but nope, he’s still having trouble with his woman. That’s where we are with socialism now.” — Megan McArdle [35:56]

Original Tone Highlights

The conversation maintains The Dispatch's signature: intellectually sharp, irreverent, deeply informed but wry and skeptical. It mixes empirical foreign policy analysis with pop-culture riffs and pointed jokes, especially at political tropes on both left and right.

Conclusion

The panel concludes that Cuba is more vulnerable and exposed than at any point in decades. The Trump administration is not just maintaining pressure but taking positive steps to force a regime crisis, with political calculations (especially for figures like Marco Rubio) at the fore. Yet all agree: regime change in Cuba would be far messier and more complicated than past interventions, with risks of chaos, refugee flows, and unpredictable political fallout domestically.

For listeners seeking a thorough, witty, and historically grounded dissection of Cuba’s impending tipping point, this episode is essential.

The Dispatch Podcast — “How Far Will Trump Go in Cuba?”

Episode Overview

Key Discussion Points & Insights

1. Cuba’s Blackout Crisis – Origins and Impacts

[01:59–05:50] Gil Guerra Explainer

Grid Collapse: Cuba’s electricity grid, reliant on Soviet-era diesel plants, began failing after COVID-19 decimated tourism and Venezuela ceased subsidized oil. Recent blackouts—worse than anything since 2004—have now triggered mass protests.
Why It Matters: Cubans rely on electricity for stockpiling food; blackouts destroy food reserves and make everyday life unlivable. The regime’s model of pacifying citizens through basic provisions is breaking down.
Escalating Protests: Recent protests have eclipsed the 2021 July 11 demonstrations in duration, though harsh police crackdowns have stemmed intensity.
External Factors: Trump administration allowed Russian oil deliveries, temporarily alleviating shortages. The prevailing U.S. policy appears focused on creating conditions for Cuba’s collapse, gambling on internal regime change.
“There are a number of different factors that are unique to this time period and this moment in history that make it more complicated and also more volatile than U.S.-Cuba relations have ever been.” — Gil Guerra [05:48]

2. Should the U.S. Make Cuba a Foreign Policy Priority?

[05:50–10:21] Kevin Williamson’s Perspective

Questioning Priorities: Williamson explains U.S. focus on Cuba is largely inertia—a Cold War legacy—while other hemisphere crises (e.g., Haiti) are ignored.
Sanctions Skepticism: U.S. sanctions deliver suffering but don’t topple regimes; effective only as part of a larger strategy, which the U.S. never pursues.
Energy Lessons: The crisis highlights both Cuba's vulnerabilities and American energy strengths.
Quip: “I understand that Marco Rubio probably will be the viceroy of Cuba on top of his other 11 jobs…” — Kevin Williamson [09:33]

3. The Unique Dilemmas of Cuban Regime Change

[10:21–13:32] Megan McArdle Adds Nuance

Historical Context: U.S. efforts to topple Cuba once made strategic sense—Cuba hosted Soviet missiles, exported revolution and security services.
Now It’s Different: After ~60 years, few Cubans remember capitalism; rebuilding would resemble post-Soviet Russia more than Eastern Europe. The risk of chaos, refugees, and responsibility for “nation-building” weighs heavily.
“We could end up with a worse situation on our hands that we will be partly responsible for and we'll have to deal with. There will be floods of refugees.” — Megan McArdle [12:54]

4. The Hawkish Case for Intervention and Its Limits

[13:32–16:10] Gil Guerra Responds

Cuba Needs External Patrons: Historically, Cuba has only survived via external support—first the USSR, now Russia and China.
Chinese Influence: China has set up surveillance outposts in Cuba; ignoring Cuba lets adversaries stake out a base near the U.S.
Myth of Refugee Floods: Largest Cuban refugee waves (Mariel boatlift, etc.) came during periods of U.S. engagement, not confrontation.
Regional Dynamics: Cuba remains a hub for anti-U.S. agitation across Latin America.

5. Post-Communist “Muscle Memory”: The Challenge of Transition

[16:10–19:54] Robust Debate: Black Markets, Culture, and Diaspora

Muscle Memory? Goldberg argues Cuba’s robust black market might give it entrepreneurial “muscle memory” after a collapse; McArdle cautions that capitalism’s success rests on shared norms, reputation, and rule of law—not mere trade.
The Diaspora Variable: Many Cuban Americans and their descendants are well-integrated and may not “return” in droves if the regime falls, unlike other post-diaspora scenarios.

6. U.S. Legal Logic for Intervention: Pretexts and Triggers

[24:19–27:26] How Would Trump Justify It Legally?

Possible Playbook: The panel discusses how the Trump administration might manufacture a legal rationale—e.g., leveraging crackdowns on protests as a humanitarian pretext.
Succession Uncertainty: The looming death of Raul Castro (age 92) creates a potential power vacuum; “playboy” grandsons lack authority with the security services.
Rubio’s Political Stakes: Marco Rubio’s political future is intimately tied to Cuba policy; failure in Cuba could tarnish his standing.

“The plan seems to be to push Cuba towards some state of collapse or some state of an internal conflict that we will then have a justification for intervening on behalf of.”
— Gil Guerra [24:30]

7. Cuba as a Left-Wing Cultural Touchstone

[31:48–36:45] The “Romance” of Cuban Socialism

Still a Beacon? The left has long mythologized Cuba as a model (however illusory) of egalitarianism, health care, and artistic freedom.
Psychological Impact: Collapse of Cuban communism would be rationalized as “rapacious capitalism destroying a beautiful experiment” rather than a failure of socialism itself.
“Socialism at this point is sort of like a joke I once heard—a blues musician with 13 albums, and you keep buying each new one thinking, this is the one where it works out. But nope, he’s still having some trouble with his woman. And that’s where we are with socialism now.” — Megan McArdle [35:56]

8. Race, Inequality, and Who Is Left in Cuba

[37:18–41:19]

Broken Myths: Despite claims of racial enlightenment, real Cuban power structures remain disproportionately white and central; the most marginalized have little recourse and endure the worst hardships.
Mass Exodus: From 2020–2025, Cuba lost nearly 10% of its population—those left behind are typically young, old, or lack foreign ties (disproportionately Afro-Cuban).

“The way that Cuba has been portrayed as this paradise evolved past racism is completely false, and actually many of those prejudices are perhaps stronger in Cuba.”
— Gil Guerra [39:00]

9. Forecasting: Is Cuba Really ‘Next’?

[41:19–43:53] Foreign Policy Punditry

Depends on Iran? McArdle argues that Trump will only proceed if operations in Iran seem successful and politically advantageous.
Momentum Argument: If Iran “succeeds,” Trump may see an opening for a rapid Cuba intervention as a crowning foreign policy triumph. Others think that even a messy Iran operation could increase pressure for “success” elsewhere.
Difficulty: Cuba is, on paper, an easier target: closer, smaller, militarily weaker than Iran or Venezuela.

10. U.S. Political Reactions — Both Sides Predicted

[43:53–48:57] How Will the Left and Right Respond?

Progressive Reaction: Expected to frame Cuba’s collapse not as a failure of socialism, but as a victim of U.S. aggression.
On the Right: The MAGA base supports hardline moves in the hemisphere (Venezuela, Iran); Cuba may excite less actual passion. Few expect a MAGA revolt, even among nationalist critics.
Rubio’s Role: Rubio seen as the key driver, with Trump eager for a “historic” legacy.

Notable Quotes & Segments

“[In Cuba,] often you have serf wages except for the nobility, and the population left is mainly elderly, very young, or Afro-Cubans without family abroad. Cuba's reality is very different from its romanticized narrative.”
— Gil Guerra [41:00]

“We now have a really poisonous form of trolly, racist, anti-semitic youth politics that is increasingly, as the author says, institutionalized.”
— Jonah Goldberg, referencing a recent Dispatch article [54:44]

“If you're watching your news instead of reading your news, you're getting garbage. And if you are going to be relying on AI for doing anything, that's beyond the sort of stuff Megan's talking about... it's going to be useful in that kind of way. I also have never had an assistant, so it's the one thing in life I really want other than a private jet.”
— Kevin Williamson [64:32]

Timestamps for Important Segments

[01:59] — Gil Guerra’s overview of Cuba’s blackouts and economic collapse
[05:50] — Kevin Williamson on U.S. Cuba policy and the limits of sanctions
[11:12] — Megan McArdle on why Cuba regime change is more fraught than ever
[13:32] — “Cuba Hawk” arguments and the continuing regional security case
[16:10–19:54] — Diaspora dynamics, muscle memory debate, U.S. intervention risks
[24:19] — Legal pretexts for intervention, succession politics in Havana, Rubio's interests
[31:48] — The U.S. political romance with Cuban socialism and its cultural afterlife
[37:18] — Realities of race and power in Cuba post-blackout exodus
[41:19] — Predictions: Will Cuba truly be next after Iran/Venezuela?
[43:53] — Expected left/right U.S. reactions if Trump intervenes in Cuba
[52:08] — Panel’s Dispatch recommendations

Noteworthy Moments

Podcast banter: The hosts mock stereotypes about podcasting voices (Rick Astley reference) and fantasize about McDonald’s, KFCs opening in post-communist Cuba.
Mock “regime change TV movie casting”: Gil Guerra as “young Marco Rubio.” [13:51]
Socialist blues joke: “It’s like the blues musician with 13 albums—each time you think it’ll work out, but nope, he’s still having trouble with his woman. That’s where we are with socialism now.” — Megan McArdle [35:56]

Original Tone Highlights

Conclusion

For listeners seeking a thorough, witty, and historically grounded dissection of Cuba’s impending tipping point, this episode is essential.

How Far Will Trump Go in Cuba?

Summary

The Dispatch Podcast — “How Far Will Trump Go in Cuba?”

Episode Overview

Key Discussion Points & Insights

1. Cuba’s Blackout Crisis – Origins and Impacts

2. Should the U.S. Make Cuba a Foreign Policy Priority?

3. The Unique Dilemmas of Cuban Regime Change

4. The Hawkish Case for Intervention and Its Limits

5. Post-Communist “Muscle Memory”: The Challenge of Transition

6. U.S. Legal Logic for Intervention: Pretexts and Triggers

7. Cuba as a Left-Wing Cultural Touchstone

8. Race, Inequality, and Who Is Left in Cuba

9. Forecasting: Is Cuba Really ‘Next’?

10. U.S. Political Reactions — Both Sides Predicted

Notable Quotes & Segments

Timestamps for Important Segments

Recommended Dispatch Reads (Panel Picks)

Noteworthy Moments

Original Tone Highlights

Conclusion

Summary

The Dispatch Podcast — “How Far Will Trump Go in Cuba?”

Episode Overview

Key Discussion Points & Insights

1. Cuba’s Blackout Crisis – Origins and Impacts

2. Should the U.S. Make Cuba a Foreign Policy Priority?

3. The Unique Dilemmas of Cuban Regime Change

4. The Hawkish Case for Intervention and Its Limits

5. Post-Communist “Muscle Memory”: The Challenge of Transition

6. U.S. Legal Logic for Intervention: Pretexts and Triggers

7. Cuba as a Left-Wing Cultural Touchstone

8. Race, Inequality, and Who Is Left in Cuba

9. Forecasting: Is Cuba Really ‘Next’?

10. U.S. Political Reactions — Both Sides Predicted

Notable Quotes & Segments

Timestamps for Important Segments

Recommended Dispatch Reads (Panel Picks)

Noteworthy Moments

Original Tone Highlights

Conclusion