Conversations with Bill Kristol

“You have to look at the strange new thing about US foreign policy. It’s not being made by diplomats. It’s not being made just by Marco Rubio. It’s being made by this group of businesspeople connected to Trump.”
So argues Pulitzer Prize winning historian Anne Applebaum in a wide-ranging Conversation about how private business interests connected to Trump are shaping US foreign policy towards Russia, Ukraine, Venezuela, and elsewhere. Drawing on her recent reporting from Venezuela, she describes how the administration propped up Maduro’s vice president and partnered with one of the country’s most notorious regime cronies. Pointing to the recent electoral success of an anti-corruption political movement in Serbia, and the defeat of Flávio Bolsonaro in Brazil, Applebaum argues that grassroots anti-corruption movements can prevail against the corruption and kleptocracy of authoritarian leaders.

"For the first time ever, the United States homeland cannot be taken for granted as a secure rear area against non-nuclear attacks."
So argues Steve Rosen, professor emeritus of government at Harvard, in a bracing Conversation on the radically new security environment created by AI, precision strike weapons including drones, and cyber capabilities. Because these technologies give a distinct advantage to the offense, Rosen contends the US must "think about ways of similarly putting adversary assets at risk." He also explains what twentieth-century history can teach us about mobilizing the nation's resources in government, industry, and the wider community of experts, to counter critical threats to America and the free world.

Where do things stand in the wars in Ukraine and Iran? What are the implications of these wars for military technology, the future of warfare, and our highly fluid geopolitical environment?
In this Conversation, Phillips O'Brien, the distinguished military historian and author of the indispensable Phillips's Newsletter on Substack, shares his perspective on the two major wars. O’Brien also considers the ramifications for US-China military and technological competition, the future of the Middle East, and the faultlines in Europe. This is an unusually incisive analysis of both the facts on the ground and the larger and gathering geopolitical threats we face.

We are less than seven weeks away from Election Day, and early voting already has begun in some states.
To discuss where things stand and where American politics might go after the midterms, we are joined again by David Axelrod, chief strategist for Barack Obama’s presidential campaigns in 2008 and 2012. Axelrod shares his perspective on how the election might play out when Trump “is in a deep hole and keeps on digging.” He explains how the fundamentals point toward a historically bad year for Republicans—with a war and tariffs, unmistakably the president's own doing, felt acutely by voters through rising energy costs. Kristol and Axelrod also discuss how the Democratic Party is dealing with the rise of economic populism, and where both parties might go in terms of ideology and character of candidates as we look toward the presidential race in 2028.

"We're 60 days away from a completely different political environment. And I think people are underestimating how different it's going to be, and how volatile it's going to be without really any moorings for either party."

So argues Doug Sosnik, former political director for Bill Clinton, one of the shrewdest analysts of American politics, and the author of an indispensable new Substack. In this detailed and wide-ranging Conversation on the midterms, 2028, and the instability of American politics, Sosnik explains what polls and historical precedents can and cannot capture about our volatile electorate. Sosnik and Kristol discuss the the strength of populist forces, the challenges facing both parties in the lead up to 2028, and why 2029 may be the beginning of a new era in American political history.