Is Cuba About to Fall? A 35-Year CIA Analyst on What Comes Next

Everyone is calling it another Iraq. Sir Richard Dearlove disagrees. In this episode of One Decision In Brief, the former MI6 chief makes the case that what's unfolding in Iran may be something different: the final chapter of a decades-long conflict, with a window for the United States to actually close it. Sir Richard and guest co-host Baroness Ayesha Hazarika break down the military logic — why Kharg Island is the likely first target, what securing the Strait of Hormuz would actually take, and whether a ground operation could stay limited. They also assess Iran's internal fractures, Russia's quiet role, China's conspicuous absence, and what the Gulf States really want from Washington right now. Is this the moment the West finally resolves the Iran question, or the beginning of something far worse? In this episode: 07:09 Uranium Extraction Scenario 09:14 Avoiding a Land Quagmire 10:58 Trump’s Legacy Calculus 11:52 Russia Helps; China Absent 13:39 Will Gulf States Choose America? Hosted by Sir Richard Dearlove (former MI6 Chief) and guest co-host Baroness Ayesha Hazarika (House of Lords) Learn more about your ad choices. Visit megaphone.fm/adchoices

Cuba is running out of fuel, its economy is in ruins, and 2 million of its citizens have already fled. Is the communist regime finally at its breaking point? Sir Richard Dearlove and Kate McCann sit down with Brian Latell, PhD, a 35-year CIA veteran and the agency's top Cuba and Latin America analyst. They assess whether the government can survive Trump's fuel embargo, what a transition would actually look like, and why Marco Rubio's approach may be more measured than his rhetoric suggests. In this episode: 04:19 US-Cuba Relations 10:25 Risks of Squeezing Cuba Too Hard 13:03 Can the Regime Collapse Peacefully 18:03 Who Holds Power in Havana 23:02 Intelligence Files and Biosecurity Fears 27:31 Rebuilding Cuba and Diaspora Role 29:35 What Drives Marco Rubio 31:08 One Decision to Watch Next Hosted by Sir Richard Dearlove (former MI6 Chief) and Kate McCann (Political Editor at Times Radio). Learn more about your ad choices. Visit megaphone.fm/adchoices

From an ultimatum to a “pause” in attacks, did President Donald Trump just blink, or is he playing a much larger game with Iran? Former MI6 Chief Sir Richard Dearlove and journalist Kate McCann analyze whether President Trump’s sudden shift on Iran is a genuine diplomatic opening, a calculated move to cool soaring global oil prices, or an attempt to buy time for US Marine reinforcements to arrive. They also explore the potential strategic friction between the US and Israel, Trump’s broader foreign policy objectives, including Venezuela and Cuba, and the UK and Europe’s reluctant role in the escalating Iranian conflict. In this episode: 01:56 – From 48 Hour Ultimatum to Five-Day Pause 03:40 – The Fragility of Global Markets 05:26 – Are There Backchannel Talks Inside Iran? 07:48 – Escalating to De-Escalate 09:41– Israel-US Divergent Aims 11:36 – Does the Conflict Help or Hurt Trump? 15:14 – UK and Europe on the Sidelines Hosted by Sir Richard Dearlove (former MI6 Chief) and Kate McCann (Political Editor at Times Radio). Learn more about your ad choices. Visit megaphone.fm/adchoices

The Strait of Hormuz is in a chokehold. The scale of this oil supply disruption has already exceeded the shocks of the 1970s. Sir Richard Dearlove and Rosanna Lockwood sit down with Helima Croft, Managing Director and Head of Global Commodity Strategy at RBC Capital Markets and former senior CIA analyst, to break down what market players are getting wrong, why reopening the Strait is far harder than it looks, and what a Houthi entry into the conflict could mean for the Red Sea.  In this episode: 3:04 Technical Side of Supply Disruption  6:11 IEA and Comparison to Russia-Ukraine  9:32 Alternative Routes for Oil and Gas  12:08 Russia is the Big Winner 13:13 Ground Troops Needed to Open the Strait of Hormuz  17:14 The US Domestic Picture  21:43 Will Houthis Disrupt the Red Sea?  27:52 What Market Participants Are Not Understanding 30:57 Is $200 Barrel Crude Oil Possible?  33:19 Sir Richard and Rosanna Discussion   Hosted by Sir Richard Dearlove (former MI6 Chief) and Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

President Trump’s call for naval assistance in the Strait of Hormuz has not been answered by European allies. Does this signal a growing crisis of confidence in the West? Former MI6 Chief Sir Richard Dearlove and international journalist Rosanna Lockwood examine the latest developments in the war with Iran, as well as rising political polarization in France and the UK, fears of domestic terrorist attacks in the West, and the critical importance of Kharg Island to the global energy market. In this episode: 01:48 – The divisive dilemma at the Strait of Hormuz 04:05 – Fears of Iranian proxy terror attacks in the West 06:14 – Political polarization in European elections 12:45 – Iran’s internal media strategy 14:47 – The strategic importance of Kharg Island Hosted by Sir Richard Dearlove (former MI6 Chief) and guest co-host Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

What exactly drove President Donald Trump’s decision to join Israel in joint strikes against Iran? Ronen Bergman joins from Tel Aviv where he is a Senior Correspondent for Military and Intelligence Affairs for Yedioth Ahronoth and staff writer for The New York Times Magazine. He shares his reporting of how Netanyahu moved Trump toward a joint strike, and why he's staying quiet about it for now. Then, retired Lt. Col. Jonathan Conricus, former Israeli Defence Forces spokesperson and senior fellow at the Foundation for Defense of Democracies, breaks down the major Israeli military objectives and how close Israel is to achieving each one. Plus, what Arab Gulf states are privately telling Israel.  In this episode: 01:24 New Leader Wounded 06:42 Israel Aims And Limits 09:36 Regime Change Doubts 16:14 Israeli Public Mood 23:30 Intel Airpower Strategy 25:12 Introducing LT. COL. (RET.) Jonathan Conricus  29:48 Strait of Hormuz Threat 32:45 Stopping Enriched Uranium 36:21 War Communications as Force Multiplier  40:55 Regime Change Scenarios 43:58 Gulf States Defense  Show Notes:  Iran’s New Supreme Leader Was Wounded Early in the War, Iranian and Israeli Officials Say - The New York Times  Hosted by Sir Richard Dearlove (former MI6 Chief) and Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

One of the few Americans briefed before US hit Iran sits down with Sir Richard Dearlove and Rosanna Lockwood to share his analysis: the legal justification is false, the strategic endgame doesn't exist, and we may have just handed Iran every reason to build a nuclear weapon. US Representative Jim Himes (D-CT), Ranking Member of the House Intelligence Committee, breaks down Trump's grip on Capitol Hill, and whether the only exit is a face-saving declaration of victory. Recorded March 9th, 2025. Hosted by Sir Richard Dearlove (former MI6 Chief) and guest co-host Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

Mojtaba Khamenei has been appointed to succeed his father as Supreme Leader of Iran. What now? Former UK Defence Secretary Sir Ben Wallace, who spent eight years as Chairman of the British–Iran Parliamentary Group, views this as a doubling down on defiance. Former MI6 Chief Sir Richard Dearlove and international journalist Rosanna Lockwood break down the rationale behind why the IRGC is vested in maintaining the status quo, the growing rift between the United States’s strategy and Gulf States Allies, and whether or not the United States and Israel have a viable endgame.Plus: Already at $100 per barrel, how high will the price of oil climb? What impact will the conflict in Iran have on European security and economies? Are Russia and China giving Iran an intelligence edge? In this episode: 01:10 Succession in Tehran 02:56 The IRGC as a Business Cartel 04:10 The Gulf States’ Perspective 06:55 UAE Business Backlash 10:26 Insurance and War Risk Shock 14:10 Shahi Drones and Escalation Risks 17:51 EU and UK Economic Hit 19:33 UK Politics and Social Tensions 21:38 One Decision to Watch Hosted by Sir Richard Dearlove (former MI6 Chief), Sir Ben Wallace (former UK Defence Secretary) and guest co-host Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

Iran's strategy isn't to defeat the US militarily. Trita Parsi argues that it's to make the cost high enough, fast enough, to collapse domestic support before Iran loses. With MAGA turning against the war, oil markets destabilizing, and both parties alarmed by talk of ground troops, Trump urgently needs a face-saving exit. Plus, Parsi believes that Iran's revolutionary system was built to withstand exactly this kind of pressure. Trita Parsi is the co-founder and Executive Vice President of the Quincy Institute for Responsible Statecraft, co-founder and former president of the National Iranian American Council, and author of four books on US foreign policy in the Middle East.  In this episode: 01:19 Succession After Assassination 03:13 Army vs IRGC Dynamics 10:55 Iran Strategy and US Politics 15:44 Why No Uprising 22:42 Gulf States Security Fallout 25:43 Saudi Shift After Oct 7 30:03 MAGA Backlash and Exit Ramps 33:32 Why Trump Went In 39:56 One Decision to Watch Hosted by Sir Richard Dearlove (former MI6 Chief) and guest co-host Rosanna Lockwood (International Journalist) Learn more about your ad choices. Visit megaphone.fm/adchoices

Former National Security Advisor John Bolton doesn't mince words: the opening strikes on Iran were just the beginning. In this special bonus episode, Bolton breaks down why he believes the Iranian regime will fragment from within, what the Gulf Arab states are about to do, and how war in Iran affects Russia, Ukraine, and China.  Then, retired Lt. General Mark Hertling brings the view from the ground. A veteran of multiple Iraq deployments and the former Chief of War Plans on the Joint Staff. Hertling has seen this before. He's asking the question nobody in Washington seems to want to answer: Is there actually a plan for the day after the strikes? In this episode: 01:31 John Bolton 04:32 Power Vacuum Risks 08:44 Gulf States Reaction 10:50 Iran Retaliation Strategy 15:16 Israel Influence Question 17:03 Oil Shock And Putin 19:51 China And Taiwan  23:34 Deterrence And Alliances 29:51 Lt. Gen. Mark Hertling 34:28 Decapitation and Unrest 36:24 Iraq Lessons on Disbandment 42:02 Intel Gaps and Planning 52:19 Wider Regional Fallout Show Notes:  Opinion | With attack on Iran, U.S. deterrence is being restored - The Washington Post  Order Mark Harling’s book: If I Don’t Return: A Father’s Wartime Journal Lt. General Mark Hertling recorded on March 2, and Amb. John Bolton recorded on March 3.  Hosted by Sir Richard Dearlove (former MI6 Chief) and Kate McCann (Political Editor at Times Radio).  Learn more about your ad choices. Visit megaphone.fm/adchoices