Timothy Snyder on Iran, Ukraine, and the Future of Freedom

Trump’s Election Playbook, Explained by Jocelyn Benson

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. Subscribe to The Long Game on Substack [https://thelonggame.substack.com/] for access to video versions of exclusive podcast segments, transcripts, and more. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video version of this episode on YouTube [https://www.youtube.com/@podlonggame]. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Photo credit:  Kent Nishimura / Los Angeles Times via Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Heather Cox Richardson on Democracy, Alliances, and America's Future

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. Follow The Long Game so you never miss an episode. New episodes drop weekly. For exclusive podcast segments, become a member of the Long Game on Substack [https://thelonggame.substack.com/]or Apple [https://podcasts.apple.com/us/podcast/the-long-game-with-jake-sullivan-and-jon-finer/id1850526014].  Show notes are available here. Transcript here [https://thelonggame.substack.com/s/transcripts]. Watch the video version of this episode on YouTube. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

America at 250: A Net Assessment (w/ Robert Kagan)

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. Follow The Long Game so you never miss an episode. New episodes drop weekly. For exclusive podcast segments, become a member of the Long Game on Substack [https://thelonggame.substack.com/]or Apple [https://podcasts.apple.com/us/podcast/the-long-game-with-jake-sullivan-and-jon-finer/id1850526014].  Show notes are available here. Watch the video version of this episode on YouTube. Transcript here [https://thelonggame.substack.com/s/transcripts]. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Timothy Snyder on Iran, Ukraine, and the Future of Freedom

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.  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 [https://thelonggame.substack.com/s/transcripts]. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Did America Lose the Iran War? (w/ Ambassador Wendy Sherman)

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 [https://thelonggame.substack.com/s/transcripts]. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]