The Long Game with Jake Sullivan and Jon Finer

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.

Access 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 longgame@voxmedia.com.

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

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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

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.

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 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.

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.

Subscribe to The Long Game on Substack for access to video versions of exclusive podcast segments, transcripts, and more: https://thelonggame.substack.com/

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

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.
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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.

Subscribe to The Long Game on Substack for access to exclusive podcast segments, transcripts, and more: https://thelonggame.substack.com/

Watch the video version of this episode on YouTube.

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.

Photo credit: Danylo Antoniuk/Anadolu via Getty Images
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