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An outsider Democrat taking on both parties in Iowa | On the Road Aug 29, 2026

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In an episode from another great Politico show, On the Road, Jonathan Martin sits down with Iowa gubernatorial candidate Rob Sand at the Iowa State Fair to talk politics over a pork tenderloin and a deep-fried Twinkie.

Sand, a Democrat running in a state that has shifted sharply to the right, makes the case that Iowa voters are fed up with one-party control, corruption and politics as usual. He discusses why Democrats have lost ground in rural America, whether the party has become too focused on insiders and national politics, and how he would govern with a Republican legislature.

Sand also weighs in on the future of the Democratic Party, his unlikely friendships with Republican governors — and his brief career as a model.

He went after social media. AI is next. (with Jonathan Haidt) | The Conversation Aug 23, 2026

Show notes

Social psychologist and “The Anxious Generation” author Jonathan Haidt helped turn concerns about kids and social media into a global political movement. Now, as Meta faces a consequential trial over youth safety and addiction, Haidt tells Dasha why he believes the courts may succeed where Congress has failed — and why the fight is only getting bigger.

Haidt also sounds the alarm on AI, warning that the threats to children could go “far beyond” social media and arguing that policymakers can’t afford to give AI companies the same free pass. And with restrictions on social media gaining bipartisan support, he weighs whether protecting kids from Big Tech could become a winning issue at the ballot box.

Have thoughts for the show? Text or leave us a voicemail at 202-643-1536.

Pete Buttigieg has a theory for how Democrats can win | On the Road Aug 22, 2026

Show notes

Former Transportation Secretary Pete Buttigieg joins POLITICO’s Jonathan Martin in Traverse City, Michigan, to discuss the future of the Democratic Party and why he believes Democrats can't simply campaign on a return to the pre-Trump status quo.

Buttigieg argues the party needs to "build what's next," weighs in on the Michigan Senate race, reflects on his time in the Biden administration, and shares his vision for institutional reform, AI, economic inequality and the road to 2028. Plus, he gives Jonathan a tour of his adopted hometown—including a stop for Traverse City's famous cherry ice cream.

Trump tests endorsement in South Carolina Aug 21, 2026

Show notes

Two power players land in South Carolina today. President Trump is hitting the trail for Darline Graham after her rocky debate on Tuesday, while Pete Buttigieg stumps for Nancy Lacore. What are the larger picture stakes of these visits ahead of the midterms and leading into 2028? Then Playbook’s Adam Wren and Megan Messerly invite POLITICO Albany bureau chief Nick Reisman to discuss other stories animating Washington: how the Knicks owner became a GOP power player, why puppies are now a campaign strategy, and Trump’s latest side gig – IndyCar opening act.

For more news and analysis, subscribe to the Playbook newsletter: politico.com/playbook

Scott Jennings’ public audition Aug 20, 2026

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Is Scott Jennings auditioning for the White House briefing room? The CNN conservative went to the mat defending Trump aide Natalie Harp just as his name is circulating as a possible next press secretary. Playbook’s Dasha Burns and Will Steakin unpack what his performance tells us about the job he may want — and new details about another major White House departure. Then, Playbook contributor Megan Messerly joins the panel to talk about what the 2026 primaries tell us about the fading power of the original anti-Trump Resistance, Darline Graham’s rough foreign-policy moment shaking up the South Carolina Senate runoff, and Donald Trump unveiling his new White House helipad. Plus, Harry and Meghan may be headed back to Britain — but is America’s right wing ready to say goodbye?

Florida’s surprising primary results Aug 19, 2026

Show notes

Another primary night of surprises — this time in Florida, where a DSA candidate upset the establishment Democrat in the race for U.S. Senate. Florida Playbook author Kimberly Leonard joins Megan Messerly and Will Steakin to discuss. Then we dig into the data center dominance this midterm, more from Jon Ossoff's attack on Trump, and an essay from The Atlantic with a surprising revelation about Mike Pence.

For more news and analysis, subscribe to the Playbook newsletter: politico.com/playbook

‘Bobby unleashed’ on the campaign trail Aug 18, 2026

Show notes

The White House is serious about mobilizing Make American Healthy Again – sending RKF Jr. out on the trail in Iowa today. Playbook co-author Dasha Burns shares what Republican Iowa gubernatorial candidate Zach Lahn has to say on the future of the MAHA movement. Then Playbook co-author Will Steakin and POLITICO polling and campaigns reporter Erin Doherty join Dasha to discuss Jon Ossoff’s new attack line on President Trump and U.S. Attorney Jeanine Pirro's latest vandalism crusade.

For more news and analysis, subscribe to the Playbook newsletter: politico.com/playbook

Mark Kelly’s next frontier Aug 17, 2026

Show notes

Sen. Mark Kelly is raising money, building political chits and showing up in politically significant states. All signs point to a 2028 run, but what is Kelly actually saying? Then Playbook co-authors Dasha Burns and Adam Wren invite POLITICO’s Daniel Miller to discuss the “runaway production” crisis in Hollywood and Mayor Karen Bass’ pothole pitfall. Plus, to mark the launch of Canberra Playbook, Australia Launch Editor Ryan Heath joins us for a special 200-second interview on what Washington should be watching in Australian politics.

For more news and analysis, subscribe to the Playbook newsletter: politico.com/playbook

How DSA progressives and centrist Dems can both win (with Sen. Adam Schiff) | The Conversation Aug 16, 2026

Show notes

In a live taping of "The Conversation" in Sacramento, Sen. Adam Schiff (D-Calif.) weighs in on whether insurgent candidates on the left could become a liability for Democrats — and on how the party should reckon with its past embrace of “woke” politics.

Dasha also presses Schiff on where he stands on California’s proposed billionaire tax, his opposition to recent arms sales to Israel, and whether he’ll continue accepting support from AIPAC.

Have thoughts for the show? Text or leave us a voicemail at 202-643-1536.

Who can replace Karoline Leavitt? Aug 14, 2026

Show notes

Karoline Leavitt’s departure leaves a major hole in the White House communications shop — but Donald Trump appears to be in no rush to replace her. Playbook’s Megan Messerly and Will Steakin unpack why, what Leavitt’s legacy will be and how Trump’s role as his own chief messenger could shape what comes next. Then, Ali Bianco joins with a scorecard of Congress’ biggest social media stars, Abdul El-Sayed’s Blue’s Clues moment draws conservative ire, and the Max Miller controversy spills into a key New York House race. Plus, a preview of Dasha Burns’ conversation with Sen. Adam Schiff.

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