Conversations with Bill Kristol

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.

“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.

Much has happened since we were last joined by Pulitzer Prize-winning historian Anne Applebaum in February, including the Trump-Putin summit in Alaska and the Zelensky visit to the White House that provoked an alarmed and last-minute rush to join by European heads of state. In this Conversation, Applebaum shares her perspective on the situation on the ground in Ukraine and the response in European capitals to reduced US support for Ukraine on the battlefield. Drawing on her recent book Autocracy, Inc, out this week in paperback, Applebaum considers the growing authoritarian threat and dangers to liberal democracy on both sides of the Atlantic. As she states, “the farther you go down the road [to authoritarianism], the harder it becomes to turn back.”

Six months in, what has the Trump administration done with immigration and deportation—and what have we learned about where it may be headed? To discuss, we are joined, again, by Aaron Reichlin-Melnick. A leading expert on immigration and Senior Fellow at the American Immigration Council, Reichlin-Melnick presents an in-depth analysis of the situation that goes beyond the headlines. As he puts it: “We are seeing a pace of enforcement unlike anything we’ve really seen in decades….with [immigration] as the Trump Administration’s top priority. It has surged resources, manpower, and attention to immigration enforcement, with the goal of massively ramping up arrests, detentions, and deportations.” Reichlin-Melnick shares his perspective on the situation on the ground now—as well as how developments such as the massive increase in funding in the reconciliation bill might affect things in the months and years ahead.

Where do things stand in the war—and what will the future of Iran look like when the fighting stops? To discuss these questions, we are joined again by Ray Takeyh, a senior fellow at the Council on Foreign Relations and one of the leading historians and analysts of Iran. Takeyh emphasizes that the Iranian leaders are “traumatized and stunned,” and that “the regime is facing a vast array of problems” from widespread discontent among the people to serious divisions within the elites. He explains that the extent of the apparent collaboration with Israel, including at the highest levels of the state, is itself evidence of the grave threat to the regime from within. Cautioning that much remains unknown and will be dependent on the course of the war, Takeyh reflects on possible paths forward for the regime. “I have always believed that the post Islamic Republic Iran will be substantially better than the Islamic Republic,” he explains. “But the principal challenge moving forward after this is what does a weaker Islamic Republic mean for regional security? Regimes that lose wars tend to behave in very unpredictable ways. Because what the regime will have to do is reconstitute the fear barrier that it relies on for its rule at home.”

What have we learned about the White House in Trump's second term? How are decisions made in the most consequential areas of national security? During the past week, Trump fired National Security Advisor Mike Waltz. To discuss this and many other matters, we are joined again by John Bolton, who served as National Security Advisor in the Trump White House from 2018 to 2019. Bolton shares the perspective of an insider who understands Donald Trump—and government at a high level of granularity. He describes Waltz’s dismissal as emblematic of a White House in chaos. As he puts it: “more and more decisions will be made in the White House and fewer decisions in the cabinet in the second Trump term than in recent presidencies. That’s the clear message going ahead.” Assessing the price we pay, Bolton states: “[Trump] is burning through decades of effort to build up goodwill, trust, faith, reliance on America. Our friends all over the world are saying, 'You’ve taken leave of your senses.’"

What are the likely effects of Trump’s tariffs, and what do they mean for the US economy? To discuss, we are joined again by Harvard economist Jason Furman, who was Chairman of the Council of Economic Advisers in President Obama’s second term. According to Furman, Trump’s tariffs represent an enormous "shock to the system” likely to produce both short- and long-term economic pain. Furman considers both the direct and indirect effects of Trump’s policies, including the effects of uncertainty on the economy. Finally, Kristol and Furman discuss whether Congress could push back against an economic agenda likely, in Furman’s words, to produce “many more losers than winners.”