Impolitic with John Heilemann

John welcomes Jacob Weisberg, co-founder of Pushkin Industries and former editor of Slate, to discuss his new book, “Profiles in Cowardice: A Study of Collaboration in the Trump Era.” Weisberg explains how he took the format and framing of “Profiles in Courage,” John F. Kennedy’s classic examination of moral leadership in politics, and turned it inside out, focusing not on the admirable but the culpable; and why some of America’s best-known and most powerful public figures—from Jeff Bezos and Stephen Schwarzman to John Roberts, Megyn Kelly, and Mitch McConnell—became complicit in a signal feature of Donald Trump’s second term: the remarkable degree of capitulation to a president few of them like or respect and many once resisted.

John welcomes back Searchlight Institute president Adam Jentleson to discuss the post-Labor Day Senate battleground map and his new book, “Supermajority: How Democrats Can Build Lasting Power.” Jentleson explains why cautious optimism is in order about his party’s prospects of retaking the upper chamber; how the strength of James Talarico and Rob Sand (in the Texas Senate and Iowa governor’s races, respectively) are rooted in the sort of ideological heterodoxy Jentleson champions in his book; why the razor-thin margins and slim majorities of our time are historical anomalies; and the degree of compromise Democrats will need to accommodate to build governing coalitions broad enough to last.

John is joined by Lawrence Wright, Pulitzer Prize-winning author of “The Looming Tower: Al-Qaeda and the Road to 9/11,” to commemorate the 25th anniversary of the 2001 attacks on the World Trade Center and the Pentagon. Wright explains what we understand today about 9/11 that we didn't understand at the time, and what we still don’t know; how the war on terror waged in its aftermath changed America, the world, and us; and the terrible possibility that, in the end, Osama bin Laden achieved more of his goals than we care to admit.

John is joined by publisher of The Bulwark and apostate Republican strategist Sarah Longwell to discuss the midterm elections, 2028, and her new book, “How to Eat an Elephant: One Voter at a Time.” Longwell explains how large an albatross Donald Trump has become for GOP candidates up and down the ballot; why Democrats’ strong position in the polls may not be a summertime “sugar high;” and why Gavin Newsom is merely engaging in “performance art” while Jon Ossoff is “president-maxxing." She also lays out what she's learned about the electorate from conducting more than 400 focus groups in the past decade—and how it informs her new book's argument about how to permanently dismantle MAGA.

John is joined by combative California union boss Dave Regan to discuss Proposition 40, his state’s controversial ballot measure to levy a one-time, 5 percent wealth tax on its resident billionaires. Regan, Prop 40's principal architect and advocate, explains its economic benefits, political challenges, and prospects for passage. He also disses the initiative's opponents—from Silicon Valley billionaires such as Sergey Brin to Governor Gavin Newsom and his likely successor, Xavier Becerra—arguing that “they think the rest of us are stupid.”