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

Photo credit:  TSgt Rob Hazelett, PublicDomain

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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? 

Video versions of exclusive podcast segments, transcripts, and more available on Substack: https://thelonggame.substack.com/

Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame

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Photo by ANDREJ IVANOV / AFP via Getty Images

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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. 

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

Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame

Email Jake and Jon at [email protected].

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

Photo credit: Albert Llop/NurPhoto via Getty Images

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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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Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame

Email Jake and Jon at [email protected].

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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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Photo credit: Danylo Antoniuk/Anadolu via Getty Images

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

Photo credit:  Kent Nishimura / Los Angeles Times via Getty Images

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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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Show notes are available here.

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:

Whether the United States is entering a genuinely multipolar world

The future of NATO, Europe, China, and Taiwan

Democratic backsliding and the resilience of American institutions

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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For exclusive podcast segments, become a member of the Long Game on Substack or Apple. 

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Transcript here.

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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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Show notes are available here.

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Transcript here.

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

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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:

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

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

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

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.

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

Show notes are available here.

Watch the video version of this episode on YouTube.

Transcript here.

Email Jake and Jon at [email protected].

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

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