The Bulwark’s Sarah Longwell on How Democrats Can Defeat MAGA for Good
On with Kara Swisher
September 10, 2026
As ballots start to hit mailboxes ahead of the November midterms, Democrats are finally feeling some long-awaited electoral optimism. But to build a coalition that can defeat MAGA politics for good, the party will have to win back voters it's lost.
Speakers Kara Swisher, Sarah Longwell, Steve Hilton
TopicsSociety & Culture
Kara Swisher (0:00)
It's like we're Olivia Rodrigo or something.
Oh my goodness, there hasn't been this much lesbian energy on the stage since Rachel Maddow dined alone.
Hi everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher, and I'm Kara Swisher. We're less than two months away from the midterm elections, and Democrats are feeling a kind of optimism they haven't felt in a while for good reason. Voters have clearly soured on President Trump as evidenced by his abysmal approval ratings. Democrats have had some big wins in recent elections, and the party in power historically struggles in the midterms. Still, the Democratic Party isn't exactly winning any popularity contests with voters right now either. If the party wants to build the kind of coalition that can consistently win elections and defeat MAGA politics for good, it will have to win back some of the voters who have abandoned Democrats over the last decade. My guest today has a blueprint to do just that. Sarah Longwell is the founder and publisher of The Bulwark and a former Republican strategist. She has a new book out called How to Eat an Elephant, One Voter at a Time. It draws on the hundreds of focus groups Sarah has done with voters since Trump first won the White House, and it offers advice to Democrats on how they can permanently defeat his authoritarian style of politics. I think it's important to listen to Republican strategists. Now, Sarah's been a real critic of President Trump, so she's not exactly a Republican anymore, but she's really well situated to help our country out of our slide into authoritarian politics because she listens to voters. All right, let's get to my conversation with Sarah. We recorded in front of a live audience last week at Sixth & I in downtown Washington, DC.
Our expert question comes from California Republican gubernatorial candidate, Steve Hilton. Don't go anywhere.
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Kara Swisher (3:54)
Sarah, thank you for coming on On.
Sarah Longwell (3:56)
Thanks for having me. It's great to be here.
Kara Swisher (4:02)
We're going to cover a lot in the conversation, Trump's unpopularity, the divide on the left between moderates and progressives, essentially punching left, and fears of the upcoming midterms. But we're going to start with your book.
You spent a decade listening and talking to voters to better understand what's happening in American politics right now. You probably heard thousands of people at this point. What's the biggest thing in general that Washington gets wrong about the kinds of voters you're hearing from, and what is the overall message you're getting now? Because it changes, goes in and out. Yes.
Sarah Longwell (4:37)
One of the stories I tell in the book is, do you remember when Donald Trump stood on the stage with Vladimir Putin in Helsinki and he sided against America's intelligence community? So I was really early in my focus grouping endeavors because we were trying to primary Donald Trump, and I really wanted to know what Republican voters thought about him.
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