The Long Game with Jake Sullivan and Jon Finer

Michael Kofman, defense analyst at the Carnegie Endowment for International Peace, returns to The Long Game as Russia intensifies its bombardment of Ukraine and decisions made in Washington reshape Kyiv’s ability to fight.

Kofman examines the gap between Russia’s military performance and its demands at the negotiating table; the leverage each side currently holds and the deadly consequences of throttling Ukrainian access to SpaceX’s Starlink and StarShield.

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References and supplemental materials

Alexander Ward, Natalie Andrews, and Josh Dawsey “Musk Ordered Starlink Slowdown That Blindsided Ukraine,” The Wall Street Journal, October 21, 2026

Photo Credit: Nikoletta Stoyanova/Getty Images

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Israelis are preparing to vote in their first election since the October 7 terrorist attacks. Barak Ravid, global affairs correspondent for Axios, joins Jake and Jon to discuss the stakes of the election. Will Benjamin Netanyahu be re-elected for a historic seventh term as prime minister?

With polls exceedingly close, Barak explains the challenge Netanyahu’s opposition will face in translating their electoral support into a governing coalition. He also weighs in on what the elections will mean for Palestinians in the West Bank and Gaza and the future of Pres. Trump’s Middle East agenda.
Drawing on his deep-sourced reporting and decades covering Israeli politics and the US-Israel relationship, Barak says October 7 is on the ballot and next week’s election will determine the future of Israeli democracy.

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Email Jake and Jon at longgame@voxmedia.com

Follow The Long Game so you never miss an episode. New episodes drop weekly. The Long Game is produced by the Vox Media Podcast Network.

References and supplemental materials

Barak Ravid and Marc Caputo, “Inside Trump, Netanyahu’s dilemma: Strike Iran before elections or wait,”Axios, October 13, 2026.

Barak Ravid, “Trump tells Axios why he endorsed Netanyahu’s reelection,”Axios, October 18, 2026.

Barak Ravid, “Biden tells Bibi he's concerned about Israel's judicial overhaul legislation,” Axios, September 20, 2023

Donald J. Trump, “President Donald J. Trump’s Comprehensive Plan to End the Gaza Conflict,”The American Presidency Project — White House press release, September 29, 2025.The American Presidency Project

P5+1, European Union, and Iran, “Joint Comprehensive Plan of Action,”US Department of State, July 14, 2015.

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President Trump has struck a diesel deal with Russia as fuel prices squeeze Americans. But what does easing restrictions on Russian exports mean for Ukraine and for efforts to end the war? Jake Sullivan and Jon Finer examine the deal’s potential economic impact, the growing tension between Washington and Kyiv, and the prospects for an energy ceasefire as winter approaches.

Then, renewed fighting between Saudi Arabia and the Houthis raises difficult questions about American commitments in the Middle East. With Saudi airports and energy infrastructure under attack, could the United States or Israel enter the fight? What could either accomplish?

Finally, an Options Memo for NATO’s Secretary General: How should the alliance respond if Russian sabotage kills civilians in a member country? Jake and Jon weigh “light,” “medium,” and “heavy” responses, exploring the challenge of restoring deterrence without triggering a wider war. Listen for the hard choices behind the headlines and the risks each carries.

Access to video versions of exclusive podcast segments, transcripts, and more on Substack:https://thelonggame.substack.com/

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The Long Game is produced by the Vox Media Podcast Network.

References and supplemental materials

•

Gen. Alexus G. Grynkewich, Supreme Allied Commander Europe, NATO, Theory of Victory: How Do We Achieve Military Success Against Russia in Deterrence and Defence?, Warsaw Security Forum, October 12, 2026.

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Feras Dalatey, “Amazon's AWS is unable to restore access to Bahrain, one UAE cloud data zone after war damage,” Reuters, September 15, 2026

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Javier Blas, Bloomberg Opinion’s energy and commodities columnist, joins Jake Sullivan and Jon Finer to explain why the Iran war has produced an oil market few expected: crude prices hovering around $100 a barrel while tankers are braving missile attacks, and sharper pain for people buying diesel, jet fuel, and heating oil.

How has China’s retreat from the oil market changed the pressure on Washington and Tehran? Why are some traders reluctant to bet on higher prices even when they fear escalation? And how long can the improvised system keeping oil moving through the Strait of Hormuz hold together?

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Anne Applebaum, Pulitzer Prize-winning author and staff writer at The Atlantic, joins Jake Sullivan and Jon Finer to discuss how far-right ideology and private profit have become intertwined in the Trump administration’s approach to the world; the subject of her new cover story for The Atlantic.

They also examine the opaque U.S. oil arrangements in Venezuela, the campaign for political influence in Greenland, and the difficult work of rebuilding American institutions and alliances after Trump.

For paid subscribers, Jake and Jon continue their conversation with Anne Applebaum. She details what changes to the White House and the Kennedy Center reveal about political power and culture in Washington.Subscribe to Long Game + on Apple or Substack for access and to support the show.

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PHOTO CREDIT

China experts Jessica Chen Weiss, David M. Lampton Professor of China Studies at Johns Hopkins SAIS, and Julian Gewirtz, fellow at Harvard’s Belfer Center and senior research scholar at Columbia University, join Jake Sullivan and Jon Finer ahead of Chinese President Xi Jinping’s state visit to Washington.

What does Xi hope to secure from President Trump—and what should the United States seek in return? Could the current truce become a durable détente, or is the relationship moving in two directions at once: greater stability at the top and deeper competition underneath? And as concern grows about advanced AI, can Washington and Beijing reduce the risks without resolving their fundamental distrust?

The conversation also examines Taiwan, rare-earth export controls, China’s expanding global role, and the choices that could shape the relationship long after this week’s summit.

For paid subscribers, Jake and Jon break down President Trump’s United Nations General Assembly speech in a special segment. Subscribe to Long Game + on Apple or Substack for access and to support the show.

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Julia Curlee, a former CIA analyst and acting senior director at the National Security Council, joins Jake Sullivan and Jon Finer to explain why she believes America’s intelligence system is being weakened from within.

Curlee also discusses her experience briefing Vice President Mike Pence and why she left government after nearly 20 years. After the interview, Then to argue for and against reaching a deal with the U.S. and continuing Beijing’s open-weight strategy.

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25 Years After 9/11: Admiral McRaven’s Warning for America

Retired Admiral William H. McRaven, former commander of U.S. Special Operations Command and Joint Special Operations Command, joins Jake Sullivan and Jon Finer as the country marks the 25th anniversary of 9/11. McRaven recalls watching the attacks while recovering from a parachute accident, and later planning and executing the operation that brought Osama bin Laden to justice.

They also examine why the Trump administration’s unexplained removal of senior military leaders could weaken candid advice and military preparedness; how special operations must adapt from counterterrorism to competition with major powers; and why America’s alliances remain essential to its security.

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Treasury Secretary Scott Bessent says the U.S. is entering “the endgame” with Iran, launching what he calls an “economic D-Day.” Closer to home, U.S.-Canada trade talks have collapsed after Prime Minister Mark Carney rejected Washington’s latest demands.

Jake Sullivan and Jon Finer examine whether Operation Economic Outcast can change Iran’s calculus, why China holds the key, and why Canadians are backing a trade fight they expect to hurt. They also stage a Red Team/Blue Team debate over President Trump’s new cyber memo, which allows private companies to conduct offensive operations against foreign cybercriminals. Jon makes the case for the so-called cyber privateers, while Jake lays out the risks.

Subscribe to The Long Game+ on Apple podcasts or on Substack for access to exclusive segments. This week, Jake and Jon tackle two listener questions: What should we make of CIA Director John Ratcliffe’s unannounced trip to Moscow? And, how did Jake and Jon manage the physical and mental toll of their years as national security advisors?

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Acclaimed investigative journalist and New Yorker staff writer Patrick Radden Keefe joins Jake Sullivan and Jon Finer to discuss his new book, London Falling.

They discuss London’s dirty-money economy, “Say Nothing” and the unfinished business of the Good Friday Agreement, whether the CIA helped spread the Scorpions’ “Wind of Change” behind the Iron Curtain, what a year inside the Pentagon taught Patrick about Washington, and why powerful people rarely see themselves as villains. At the end, Patrick, Jake and Jon share their summer reading list.

In an exclusive segment for subscribers to The Long Game+ on Apple or Substack: Patrick, Jake, and Jon examine how Trump-era impunity and outrage fatigue can normalize corruption.

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Polish Deputy Prime Minister and Foreign Minister Radosław “Radek” Sikorski joins Jake Sullivan and Jon Finer to assess Europe’s security at a moment of growing strain in the transatlantic alliance.

They discuss whether Europe can deter Russia with a reduced US military presence, how NATO should respond to Russian sabotage and possible false-flag operations, and whether America can still be counted on if Article 5 is tested.

Sikorski also lays out Ukraine’s possible path to victory, the pressure building on Russia’s economy, the prospects for tougher sanctions, China’s leverage over Vladimir Putin, and why he sees the European Union as a strategic shield for Poland and Ukraine.

Then, Jake and Jon discuss Sikorski’s strikingly cautious assessment of the US commitment to NATO—and revisit the closest they came to an Article 5 crisis while serving in the Biden administration.

For subscribers to The Long Game+ on Apple Podcasts: Jake and Jon break down the FCC’s new restrictions on foreign-made humanoid robots and connected power inverters—and what the action reveals about the widening US technology competition with China.

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Zelensky just fired his defense minister, his top general, and his prime minister in a single reshuffle — and thousands of Ukrainians poured into the streets. Jake Sullivan and Jon Finer unpack what's really driving it: a generational war over how to fight, Zelensky's wariness of rivals who outshine him, and a reckoning over corruption in military procurement. They trace how Ukraine's homegrown drone industry — now the front line of the war — grew out of a 2023 "tech sprint," and why it may soon make Ukraine one of the world's largest arms exporters.

Then, Iran. With the ceasefire dead and the Strait of Hormuz closed, Jake and Jon reopen their "options memo" — keep striking, cut a deal, go for a knockout blow, or walk away.

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Michigan Secretary of State Jocelyn Benson joins Jake Sullivan and Jon Finer to discuss the security of the 2026 midterm elections — just a day before President Trump’s primetime Thursday address, expected to focus in part on “election integrity.”

They discuss Trump’s claims about noncitizen voting, the SAVE Act, efforts to access state voter rolls, the dismantling of federal election security infrastructure, and whether federal agents could be deployed to polling places.

Then Jake and Jon debate whether Russia might escalate against NATO as Ukraine gains ground — and what that would mean for the alliance.

For subscribers to the Long Game+ on Apple: Jake and Jon break down the latest on Iran and the Strait of Hormuz, including the unraveling ceasefire and Trump’s decision to reimpose a blockade of Iranian exports.

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Historian and author of the “Letters From An American” newsletter Heather Cox Richardson joined Jake Sullivan and Jon Finer to discuss the historical roots of today's political moment, the relationship between American democracy and U.S. global leadership, the future of the international order, and what a new foreign policy for the 21st century could look like.

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Transcript here.

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As the United States approaches its 250th birthday, how should Americans assess the country's strength, its democracy, and its role in the world?

Recorded live at the Aspen Ideas Festival, Jake Sullivan and Jon Finer are joined by historian and foreign policy scholar Robert Kagan for a wide-ranging conversation on America's future. Drawing on four decades of writing about American power and the international order, Kagan argues that the United States is living through two historic shifts at once: a renewed struggle over American identity at home and a retreat from the global leadership that defined the post-World War II era.

Topics covered:

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Whether the United States is entering a genuinely multipolar world

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The future of NATO, Europe, China, and Taiwan

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Democratic backsliding and the resilience of American institutions

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What America's role in the world should look like over the next quarter century

Jake and Jon also challenge Kagan on Iraq, Iran, the use of American power abroad, and whether the United States can rebuild trust with its allies after the Trump era.

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Historian and “On Tyranny” author Timothy Snyder joins Jake Sullivan and Jon Finer to discuss the Iran war and ceasefire negotiations, the state of the Russia-Ukraine conflict, how Ukraine has transformed drone warfare, what these wars reveal about the limits of American military power, and what a positive vision of freedom looks like for the United States as it approaches its 250th anniversary.

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President Trump says the war with Iran is over. But what exactly did the United States agree to?

Ambassador Wendy Sherman, the lead U.S. negotiator of the 2015 Iran nuclear deal, joins Jake Sullivan and Jon Finer to assess the new U.S.-Iran agreement and explain why she believes it gives Tehran significant concessions while securing few meaningful nuclear constraints in return.

Topics covered:

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Whether the United States or Iran emerged with greater leverage from the war

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The future of Iran's nuclear program and its economic windfall through sanctions relief and Strait of Hormuz fees

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What the deal means for Israel, the Gulf states, and the broader Middle East

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Why diplomacy requires expertise, patience, and direct engagement with adversaries

Jake and Jon also discuss whether Congress will review the agreement, what it could mean for Russia and global energy markets, and other stories they're watching in the weeks ahead.

For transcripts, exclusive podcast segments, and more, subscribe to The Long Game on Substack. On Apple Podcasts, subscribe to The Long Game+ for exclusive audio. This week, paid subscribers get access to an exclusive segment in which Jake and Jon share behind-the-scenes stories from their own negotiations with Iranian officials during the Obama administration, including late-night bargaining sessions in Vienna, secret talks in Oman, and some of the unexpected moments that helped shape the 2015 Iran nuclear deal.

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As the World Cup kicks off, what can soccer tell us about the state of the world?

Franklin Foer, author of “How Soccer Explains the World,” joins the show to discuss why the world's most popular sport remains one of the best lenses for understanding nationalism, globalization, identity, and political power. More than twenty years after the book's original publication, Foer reflects on how globalization reshaped the game, why national identity remains a powerful force, and what the World Cup reveals about today's geopolitical landscape.

Topics covered:

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Why globalization often strengthened nationalism rather than weakened it

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The possibility of a U.S.-Iran World Cup showdown on American soil

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The roles of Saudi Arabia and Qatar, and the growing intersection of sports and geopolitics

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President Trump’s relationship with FIFA

Subscribe to The Long Game on Substack for exclusive video content, transcripts, and more. This week, paid subscribers receive the inaugural edition of The Wrap, where Jake and Jon share what they're reading, revisit something they may have gotten wrong, and discuss the issues they're watching most closely.

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More than four years into the Russia-Ukraine war, has the battlefield finally begun to shift?

Jake Sullivan and Jon Finer sit down with Michael Kofman, one of the leading analysts of the conflict, fresh off a trip to Ukraine's frontlines. Kofman argues that Ukraine is in its strongest position since 2023 and explains why Russia's grinding offensive may be running out of steam. Together, they discuss how Ukraine used drones and battlefield innovation to offset Russian advantages, why Moscow's military strategy is producing diminishing returns, and what it would take to translate recent developments on the battlefield into a lasting political settlement.

They discuss:

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Why Kofman believes Ukraine has gained the advantage for the first time in years

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How drones and decentralized defense production have transformed the battlefield

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Whether Russia can be convinced that continuing the war is futile

Subscribe to The Long Game on Substack for exclusive video content, transcripts, and more. This week, paid subscribers will receive a special mailbag segment where Jake and Jon answer listener questions.

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President Trump is simultaneously pursuing peace talks with Iran while escalating U.S. military pressure in the region following recent strikes. Jake Sullivan and Jon Finer revisit the policy options most likely facing the administration and walk through how they would advise the president at this moment of escalation and diplomacy.

Then, Ricardo Zúñiga, former Senior Director for Western Hemisphere Affairs at the National Security Council and one of the architects of the Obama administration’s opening to Cuba, joins to discuss:

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The politics behind U.S.-Cuba policy

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What Obama was trying to achieve through engagement with Havana

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How Trump’s approach to Cuba and Latin America has changed in his second term

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The likelihood that the U.S. will undertake some form of military action in Cuba

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Whether sanctions and pressure campaigns still create meaningful leverage

•

How Venezuela reshaped U.S. thinking about authoritarian regimes in the hemisphere

Follow The Long Game so you never miss an episode. New episodes drop weekly.

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Transcript coming soon.

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