The episode opens with a full Incogni sponsorship read, pitching the data broker removal service with a 60% discount. Once the hosts are on mic, Tommy and Ben immediately pivot to sports grief: the Knicks lost their playoff game the night before, and Donald Trump was shown on the jumbotron at Madison Square Garden during the national anthem — to predictable boos from the New York crowd. Ben assigns 60% of the blame to the jumbotron operator, 40% to the referees, and bemoans the Wemby takedown of Jalen Brunson. Tommy mentions that Rahm Emanuel was courtside alongside Larry David and Patriots owner Bob Kraft, noting Rahm's astonishment at the physical brutality of the game up close.

Ben shares that his book 'All We Say: The Battle for American Identity: A History in 15 Speeches' entered the New York Times bestseller list at number 5, crediting listeners and noting David Sedaris is ahead of him. He announces a tour stop in San Francisco that evening. Tommy then lays out the full episode agenda in rapid-fire fashion: the Iran-Israel ceasefire collapse and Iran shooting down a US Apache helicopter, the Jared and Ivanka Albanian island corruption scandal, the FIFA World Cup and Trump's use of it to deny visas and generate PR, Xi Jinping's visit to a surprisingly prosperous North Korea, John Bolton's classified information plea deal, the CIA officer caught with 303 gold bars, a delightful Nigerian fake-age story, and a closing interview with BBC correspondent Will Grant on Cuba's humanitarian crisis and potential US intervention.

Tommy delivers a brisk, alarming timeline of the week's events in the Middle East. Israel and Lebanon declared a ceasefire on Wednesday; by Thursday, Hezbollah — one of the two parties doing the shooting — announced it was not on board. The IDF then struck roughly 150 Hezbollah sites, prompting rocket fire into northern Israel, which led to strikes into southern Beirut — directly contradicting Trump's public assurances that Netanyahu had agreed to stop hitting Beirut. Iran then fired approximately 30 ballistic missiles directly at Israel, and the Houthis launched a missile and threatened Red Sea shipping. For a brief window, full-scale war seemed imminent. Trump intervened and called Netanyahu, but the Israeli response, while restrained by targeting a petrochemical plant and some infrastructure, showed the cycle was far from over. Ben Rhodes frames the structural problem with characteristic clarity: Netanyahu wants to destroy Hezbollah, not make peace; Trump wants to claim victory without actually achieving his objectives; and Iran wants to establish deterrence and humiliate the US-Israel alliance without triggering a full war. None of them want the deal that would end this ^{[1] — Tommy Vietor "Trump publicly said Netanyahu agreed to stop bombing Beirut. Netanyahu immediately ordered strikes on Beirut. Iran responded with 30 ballis…" 08:30 Play} .

The hosts zoom in on one of the week's most alarming details: Iran shot down a US Apache helicopter in the Strait of Hormuz. The Pentagon initially suggested it may not have been intentional — a claim Tommy finds absurd. The crew was stranded for hours in the dark ocean before being rescued by an unmanned drone system. Trump, who has spent years calling Obama weak, called the incident 'not a big deal' in a call to The Wall Street Journal. Ben recalls the GOP's outrage when sailors briefly drifted into Iranian waters during the Obama years — an incident that was resolved quickly after John Kerry called the Iranian foreign minister — and how that moment was used as a campaign talking point for years. Ben argues the Iranians are deliberately focusing military efforts on the strait to establish the subtext that they can close it even if they reopen it, and that Iran retains far more military capability than Pete Hegseth's earlier briefings suggested ^{[1] — Tommy Vietor "Iran shot down a US Apache helicopter patrolling the Strait of Hormuz, leaving the crew adrift for hours before a drone system rescued them…" 12:58 Play} . CENTCOM then announces self-defense strikes against Iran in response, and both hosts note the cycle of violence has no visible endpoint.

A video clip of Trump being questioned by reporters becomes the episode's most absurdist moment. Asked to define ceasefire, Trump explains that in that part of the world a ceasefire is simply when you're 'shooting in a more moderate manner.' He refuses to call the blockade a war and declines to define it at all. He then reveals he has renamed highly enriched uranium 'nuclear dust' because it's 'nice' and 'cute' and 'people picked it up.' Tommy's immediate response is to urge every reporter to stop letting Trump redefine words with actual dictionary definitions. Ben traces this to an original sin in media coverage: outlets repeated Trump's claim that he 'ended 8 wars' without pointing out that he hadn't ended any. The real cost of treating 'ceasefire' as something flexible: the public doesn't realize the US is spending billions sustaining a military blockade, that violence is ongoing, and that Lebanon's prime minister has counted 3,500 Israeli airstrikes since the April 16th agreement ^{[1] — Donald Trump "Trump told reporters that in the Middle East, a ceasefire simply means 'shooting in a more moderate manner.' He also renamed highly enriche…" 17:45 Play} .

Two back-to-back sponsor reads: Squarespace pitches its Blueprint AI website builder with a free trial and 10% discount at squarespace.com/world for new purchases. Wise follows with a pitch for its international money app, emphasizing zero hidden fees, mid-market exchange rates, transfers completing in 20 seconds or less, and 15 million global users — Tommy adds a personal endorsement from his own travel experience.

Ivanka Trump's podcast appearance sets up one of the episode's most satirically rich segments. In a softly lit room that Ben later jokes looks either like a podcast studio or a torture chamber, Ivanka describes the moment she and Jared 'found' the Albanian island of Sazan — they stopped for a swim off a Rothschild family yacht (confirmed by Jared on the All In podcast), hiked barefoot to the top, and were 'captivated.' Tommy provides the grounding context: Sazan is a 1,400-hectare island in the Adriatic Sea, an environmentally protected reserve home to flamingos, pelicans, seals, and turtles, with Cold War-era Soviet submarine bunkers still in place. It has been known and inhabited for millennia. Albania's anti-corruption body SPAC is investigating how the island's ecological protections were quietly removed in 2024, just in time for Jared's $1.6 billion luxury resort project with reportedly up to 10,000 hotel rooms and villas. The Albanian PM, Edi Rama, had conveniently joined Jared and Ivanka on the Rothschild yacht shortly after their 'discovery' ^{[1] — Tommy Vietor "Ivanka Trump described on a podcast how she and Jared 'discovered' the protected Albanian island of Sazan after stopping for a swim from a …" 22:50 Play} .

The protest movement is in full swing: developers erected barbed wire fences around Sazan, security guards beat a protester on video that went viral, and Albanian tour guide Dejana KJ posted a passionate Instagram video declaring the revolt was starting in Albania but would go worldwide. Ben Rhodes connects the dots on the broader pattern: Albania is a small country, Edi Rama is PM, and when the son-in-law of the US president shows up interested in your coastline, you say yes. Ben argues the development will deliver zero economic benefit to ordinary Albanians — the clientele will be the same ultra-wealthy private island set. Tommy adds that Rama's own justification — that 400 yachts are worth more than 40,000 regular tourists — is a politically toxic message when your population is rioting in the streets. The European Commission has warned the project may violate EU environmental rules, threatening Rama's core promise to get Albania into the EU ^{[1] — Ben Rhodes "Barbed wire fences went up, security guards beat protesters on video, and thousands took to the streets. The Albanian anti-corruption agenc…" 27:20 Play} .

The 2026 World Cup is a record-setter: 48 teams, three host countries (the US, Mexico, and Canada), 16 cities, and 39 days of competition with up to six games per day at peak. But the hosts have a long list of grievances. ICE will be deployed at venues under the banner of fighting counterfeit merchandise and human trafficking — a framing Tommy and Ben dismiss as cover for immigration intimidation. The Iranian team has been forced to base itself in Mexico and commute to US games. Somalia's African Referee of the Year, Omar Artan, was denied entry at Miami Airport. Haitian fans were denied visas. African journalists have struggled to get credentials. FIFA's own financial model, which Tommy explains through his conversation with Rahm Emanuel (who turned down hosting games in Chicago as mayor), extracts ticketing, broadcasting, sponsorship, concessions, and parking revenue while leaving host cities to pay for transportation, security, and even free Fan Fests. Several cities have cancelled their Fan Fests because they can't afford them. FIFA chief Gianni Infantino, meanwhile, gave Trump a FIFA Peace Prize. Ben predicts this is a dry run for Trump inserting himself into the 2028 Los Angeles Olympics ^{[1] — Tommy Vietor "The top African referee was denied entry at Miami airport. Haitian fans were turned away. Iranian players must commute from Mexico for thei…" 34:10 Play} .

Tommy reads two back-to-back sponsor spots. Helix Sleep gets a personal endorsement from Tommy — guests staying over always compliment the mattress — with a 20% sitewide discount and 120-night trial at helixsleep.com/world. Ridge Wallet follows with a Father's Day pitch: slim, premium wallets made from aluminum, titanium, and carbon fiber, built by a father and son with a lifetime warranty and up to 40% off at ridge.com/PSTW.

Chinese President Xi Jinping made his first trip to Pyongyang in seven years, with the summit shrouded in secrecy. But the run-up coverage is full of revelations: recent visitors to North Korea describe landing to find Chinese electric vehicles everywhere, rideshare apps, new restaurants including pizza joints, and a general buzz of economic activity. Satellite imagery from both The Times and the Wall Street Journal shows Pyongyang is three times brighter at night than five years ago, with full parking lots and active oil facilities. The Wall Street Journal and a South Korean think tank identify the driver: North Korean arms sales to Russia generating more than $10 billion from late 2023 through 2025, alongside deploying 16,000 soldiers to fight alongside Russian forces — a third of whom were killed or wounded ^{[1] — Tommy Vietor "Visitors to Pyongyang are reporting Chinese electric vehicles, rideshare apps, and pizza restaurants. Satellite imagery shows the capital i…" 41:20 Play} . Kim has also profited from state-backed cryptocurrency theft and hacking. Tommy acknowledges that if ordinary North Koreans have more food, that's genuinely good, but notes that repression has intensified — Kim is executing people for distributing South Korean TV shows — and the economic benefits are heavily concentrated in Pyongyang.

Ben Rhodes delivers a sweeping structural argument triggered by the North Korea economic boom: the entire edifice of US sanctions policy is broken. He recalls a time when China and Russia actually participated in enforcing sanctions on North Korea, even if imperfectly. That era is over. As the US has sanctioned Russia and piled more restrictions on China, those countries have simply pivoted to building parallel trade infrastructure — trading in crypto, bartering arms for economic support, routing transactions outside the dollar system. North Korea is now the ultimate exhibit: fully sanctioned, building infrastructure, fielding Chinese EVs, selling weapons to nuclear powers. Ben's diagnosis is that over-sanctioning creates a dynamic where sanctioned countries find each other and create an alternative economy, making US financial pressure progressively less effective ^{[1] — Ben Rhodes "North Korea is thriving despite years of US sanctions. Ben Rhodes argues this is the inevitable result of America over-sanctioning so many …" 46:47 Play} .

Two corruption stories back to back. First, John Bolton: CNN reported he will plead guilty on one count of mishandling classified information — specifically writing classified material in his diary and sharing it via personal email and a messaging app with his wife and daughter. A fine of $2.25 million is on the table, with potential prison time of up to 5 years. Iran apparently hacked Bolton's email in 2021, which may be how the case came to light. Ben notes the case involves a real underlying crime and shouldn't be lumped in with what he calls vindictive political prosecutions like those against James Comey, but acknowledges the selective enforcement given Trump's own classified document situation. Then David Rush: a CIA officer in the Directorate of Science and Technology allegedly created a fake, highly classified special access program about continuity of government operations, funneled money into it, and converted those funds into 303 gold bars worth over $40 million, plus $2 million in cash and 36 luxury watches. The FBI also found he had fabricated his academic credentials (claiming degrees from Clemson and RPI) and his Navy pilot history ^{[1] — Will Grant "A military operation against Raul Castro at 95 would inflame Cuban nationalism. Targeted action against younger leadership is possible. Boo…" 1:11:35 Play} .

Tommy saves the most whimsical story for last before the interview break. Mahmood Sadiq Buba entered the Nigerian House of Representatives race, telling everyone he was 30 years old. Voters found him inspirational — a man with dwarfism running despite long odds. Then documents surfaced showing he is actually 15 years old. A video compilation goes viral showing him being interviewed by journalists and answering questions with single words, looking every bit like the child he is. The coup de grace: footage of him riding a miniature red pony. Tommy salutes the audacity — it takes courage to run for office, he says, even more to lie about your age while having a condition that makes you look like a literal five-year-old. Ben draws a line between this endearing grift and the more predatory versions represented by Jared's Albanian island or the CIA gold bars, concluding that this one he respects.

Tommy and Ben work through the final pre-interview ad block. SimpliSafe gets a personal testimonial from Ben, who set up his own system without a drill, endorsing the app, customer support, and peace of mind; the promo is 50% off at simplisafe.com/crookedworld. ThirdLove follows with a pitch for its 60-plus size range and half-cup sizes with a $15 discount code. Then a recorded cross-promo for Hysteria, the Crooked Media podcast hosted by Erin Ryan and Alyssa Mastromonaco, billed as sharp political analysis for women with humor and zero handholding.

Tommy introduces Will Grant, the BBC's Mexico, Central America, and Cuba correspondent, who lived in Cuba for seven years beginning in 2014 and has just returned from a reporting trip. Grant draws a stark before-and-after: under the Obama opening he witnessed genuine optimism, a sense that the Cold War might truly be ending, and real dynamism among young Cubans. Today, after a series of policy reversals under Trump's first term, Biden, and now Trump's second term, Cuba is in survival mode. Since Maduro's forced removal in January caused Venezuela's oil supply to be cut off, and with Mexico under US pressure not to fill the gap, only one Russian shipment of 830,000 barrels has arrived. Cuba is producing nowhere near enough domestically. The consequences: no cars on the roads, long and arduous blackouts, hospitals running at a fraction of capacity accepting only emergencies, schools closed multiple days a week, state businesses shuttered, garbage trucks not running. Summer is approaching — heat, mosquitoes, no air conditioning or fans. Grant calls it 'incredibly bleak and actively getting worse week after week' ^{[1] — Will Grant "Since Venezuela's oil supply was cut and only one Russian shipment has arrived, Cuba has no cars on the streets, hospitals accepting only e…" 1:02:40 Play} .

Tommy presses Grant on measurable health impacts. Grant acknowledges the Cuban state controls statistics, making reliable data impossible, but describes what he witnessed: hospitals accepting only emergencies during blackouts, a maternity ward running on a large generator for basics, and a pregnant woman he followed whose baby was born in difficult but survivable circumstances thanks to hard-working individual staff. The deeper revelation is about public opinion. For years, Cubans carefully parroted state slogans when journalists put microphones in front of them. Not anymore. Grant describes hearing ordinary Cubans say brazenly that they hope Trump comes in and takes over — not because they love Trump, but because they want whatever this is to be over and want a dignified life for their children. The division is real: old-school revolutionaries are furiously anti-Trump and anti-Rubio; a significant portion of ordinary Cubans have simply lost their fear and want any exit from the current situation ^{[1] — Will Grant "For years, Cubans carefully parroted state slogans to journalists. Not anymore. Will Grant says people are now brazenly speaking out — and …" 1:06:30 Play} .

Tommy raises the extraordinary fact of CIA Director John Ratcliffe's visit to Havana, which came directly after the Venezuela operation. Grant says he was standing on the Malecón during a Cuban government-organized protest outside the US Embassy when he learned Ratcliffe had gone to Venezuela — and then showed the news to a Cuban official, watching him 'literally turn gray.' Grant walks through the message Ratcliffe likely delivered: we indicted Raul Castro, we just demonstrated in Venezuela that we are capable of military action, and more than 34 of your soldiers were killed by Delta Force in seconds. He then analyzes the Cuba operation options: a personal action against the 95-year-old Castro would inflame Cuban nationalism even among those who want change; targeted action against younger leadership is more plausible; boots on the Malecón seemed outlandish even seven months ago, as Venezuela did. The only truly safe path for Cuba, Grant says, is a negotiated solution — but it requires wholesale economic and political transformation that Rubio will demand and that Havana may not be capable of delivering ^{[1] — Will Grant "CIA Director John Ratcliffe visited Havana just days after the Venezuela operation, in which 34 Cuban security officers were killed by Delt…" 1:08:15 Play} .

Tommy pivots to ask Grant about the World Cup atmosphere in Mexico City, where Grant is based. The honest assessment: if this were Mexico's tournament alone, the city would be humming; instead, there's a muted anticipation weighed down by complications. Airport construction at Mexico City's main airport is creating chaos for arrivals. Major protests are planned by teachers' unions, transport workers, and — most poignantly — the families of Mexico's 130,000 disappeared people, who are using the World Cup's global platform to demand action. Grant visited Monterrey, a host city, and found security forces focused on normal crowd control — petty theft, minor violence — rather than cartels, who have little business incentive to disrupt international sporting events. The Iran situation adds another layer: the Iranian team is based in Tijuana, traveling to Los Angeles and Seattle for games, and Mexico's President Claudia Sheinbaum was openly proud to welcome them. Grant closes on an optimistic note: Mexicans are fantastic hosts and want this to go well — the excitement is there, it just hasn't coalesced yet.

Tommy thanks Will Grant for joining the show and the audience for listening, promising to return next week. The production credits name producers Ilona Minkowski, Michael Goldsmith, and Anisha Banerjee, with team members including Matt DeGroot, Ben Heathcote, Jordan Kanter, Kenny Moffett, David Tolls, and Ryan Young, noting the staff is unionized with the Writers Guild of America East. The episode closes with a repeated cross-promotion for Hysteria, the Crooked Media podcast hosted by Erin Ryan and Alyssa Mastromonaco.