Conversations with Bill Kristol

“Whatever happens in 2026, I think no one should take any interpretation of that as a precursor to what’s going to happen in 2028.” So argues Doug Sosnik, former political director for Bill Clinton and one of the shrewdest and most imaginative analysts of American politics. Sosnik considers possible scenarios in 2026 including a wave election year for Democrats driven by higher turnout of college-educated voters—but their prospects in a presidential election year are threatened by "atrophied support amongst all working-class voters…. that is a barrier for winning the White House in ‘28 if we can’t do better.” In his deeply perceptive and often surprising account of the state of our politics, Sosnik shares his perspective on the challenges facing both parties in the lead up to 2028—which may prove to be one of the most significant elections in American history.

“The US government wants to arrest, detain, and deport one in every 24 people in the country—4% of the US population. That cannot be done without fundamentally transforming who we are as a people and our relationship to law enforcement.”  So argues Aaron Reichlin-Melnick, a leading expert on immigration and Senior Fellow at the American Immigration Council, in a bracing Conversation on the scale and scope of the Trump administration's mass deportation mission. Reichlin-Melnick shares his perspective on the administration’s massive political and financial investment in deportation and detentions, which already have reached record levels. Kristol and Reichlin-Melnick also consider the implications of these policies for legal immigration, civil liberties, the nature of American law enforcement, and the character of American society.

“The Europeans have been in this alliance [NATO] to protect themselves, largely from Russia and other aggressors. And now it has an aggressor within the gates, so to speak. And that’s quite an extraordinary situation.”So argues the eminent political thinker Francis Fukuyama, who begins with his assessment of Trump’s bullying of Denmark and Western Europe in recent days. In a thought-provoking tour d’horizon Conversation, Fukuyama shares his perspective not only on Greenland but on a world in crisis more generally, covering Ukraine, Europe, China, Japan, as well as developments in the United States. As he puts it, in bracing terms: “Trump is doing the same thing domestically that he’s doing internationally. He’s trying to erode all the existing constraints on his ability to use power.”

Where do things stand in American politics as we head into a midterm election year?  To discuss these questions we are joined again by Ron Brownstein, a Bloomberg Opinion columnist and senior CNN political analyst. Brownstein points to President Trump’s approval rating as perhaps the most significant indicator in the 2026 midterm elections—and potentially still a major factor in 2028. As he puts it, "Amid all of the swirling currents that you get whenever Trump is in the White House… the real message of '25 was ‘the fundamental things apply.’” Brownstein shares his in-depth analysis of the current demographic and partisan fault lines in American politics, and the challenges both parties face as we look ahead to the midterms and presidential elections. 

“We take for granted the degree of peace that we’ve enjoyed over the past eight plus decades. And we think that’s the norm. The norm is actually a lot more like what the world looked like before 1945. Certainly, the previous 100 years were one of constant great power warfare. And I don’t think people are ready for that—the world that we’re now moving into.”As the distinguished historian Robert Kagan puts it in this provocative Conversation, Trump’s foreign policy may be a decisive break from the past that will not be followed by a return to the status quo. According to Kagan, we are at risk of returning to a multipolar world of shifting alliance structures and transactional foreign policy that would greatly endanger American security. Kagan’s bracing account considers the stakes of current foreign policy challenges in Asia, the Middle East, Latin America, and Europe—as well as the contest over liberal democracy at home.   

Dick Cheney (1941-2025) is widely regarded as one of the most consequential vice presidents in American history. To discus his life and legacy, we are joined by Steve Hayes, CEO and editor of The Dispatch and author of Cheney (2007), who had extraordinary access to Cheney during his time as vice president. In this Conversation, Hayes shares his personal reflections on Cheney’s character, views, and decades of public service, which spanned from the Ford through the George W. Bush administrations. Hayes reflects on the ways in which Cheney was understood—and misunderstood—by the media and public, and what the story of Cheney's life can teach us about the last half century of American political history.

How has the second Trump presidency differed from the first? How did Trump’s experiences during his time out of office and on the campaign trail in 2024—including his trial in New York and the assassination attempts—shape him? What can we expect in the months and years ahead? In this Conversation, Jonathan Karl, a leading chronicler of Donald Trump and author of Retribution: Donald Trump and the Campaign that Shaped America, argues for the centrality of retribution in understanding Donald Trump’s second presidency. Drawing on his extraordinary access to the president over many years, Karl reflects on how we got here and considers where we might be going.   

Where do things stand in the United States nine months into the second Trump administration? Where do things stand in Ukraine, and what are the implications of the war for the future of liberal democracy around the globe? In this Conversation, the distinguished historian Timothy Snyder reflects on the situation of the United States, Eastern Europe, and the politics of the current moment.    

“It’s hard for me to imagine a voter that votes in 2026 that doesn’t have Trump on their mind.”According to veteran Democratic strategist James Carville, Trump "keeps jacking the stakes up, every day” and remains the focal point of American politics as we head towards the midterms next year. As he puts it, the Republican Party has become a “personality cult” while the Democratic Party is "a coalition in search of itself." As he explains: “I don’t think Democrats can know who they are until Democratic primary voters weigh in and decide. It’s not up to me to say what the Democratic Party should be. It’s for eight people to run for president and then have Democratic primary voters pick one, and then that’s what the party becomes.” In a wide-ranging Conversation, Carville shares his distinctive perspective and characteristically shrewd insights on where our politics might be headed as we look toward the midterms and 2028.

The second Trump administration’s approach to China so far differs from the more consistently hawkish posture of the first term. To analyze the increasingly dangerous state of our geopolitical situation and the threat posed by China, we are joined again by Princeton professor Aaron Friedberg. According to Friedberg, China continues to strengthen in military, technological, and geopolitical might as it continues to advance its ties to Russia and North Korea. Meanwhile, in Washington, the position seems to be emerging that the US can make a deal with China, as well as draw back from American positions in Europe and elsewhere. As Friedberg puts it, this policy would leave American allies in Europe and Asia more vulnerable to China and Russia—countries that have their own differences but are united by an “ideology that’s anti-Western, anti-liberal, anti-democratic. And that’s a pretty powerful force.” Friedberg argues that the various and growing threats to the US and the world order remain ever more interconnected. To counter these threats, the US must increase engagement around the world and strengthen collaboration with allies—rather than “making deals” with adversaries while retreating from global commitments.