How Trump could repeat 2016

Welcome to Playbook Deep Dive, the stories behind the power. From Congress and the White House to bar stools and back rooms, POLITICO Playbook’s Ryan Lizza brings you interviews with the most compelling and important figures who explain what’s really going on in Washington.

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Michael Cohen may be the only person standing between Donald Trump and jail. Three of Trump’s four criminal trials — the ones in Washington, Florida and Georgia — seem hopelessly stalled. But on this coming Monday in New York, the hush money case is set to begin.

Deep Dive guest and former Trump lawyer Michael Cohen is the star witness in the case. On this episode, he joins host and Playbook co-author Ryan Lizza to discuss how he will defend the assault on his credibility at the trial, why Alvin Bragg’s case is stronger than analysts believe, the legal tactics he’s expecting from Trump’s team and whether he ever regrets breaking with Trump.

Michael Cohen on the first Trump trial: Prepare to be surprised

On April 1, the Florida Supreme Court issued a pair of decisions on abortion that led the Biden campaign to declare that Florida, which Democrats have lost twice to Donald Trump, was now “winnable.”

The only problem with that? Some of Florida’s abortion rights advocates want the president to stay away. At issue is Amendment 4, a measure on November’s ballot that would enshrine abortion in the state constitution — and will also need Republican and independent votes to pass. 

On this episode of Deep Dive, Anna Hochkammer, the executive director of the Florida Women’s Freedom Coalition and one of the architects of Florida’s abortion ballot initiative, joins host and Playbook co-author Ryan Lizza to discuss the delicate politics of building a bipartisan coalition around abortion rights in a red state like Florida.

Abortion will now be on the ballot in Florida. Here’s why that’s awkward for Biden.

A year ago today, Wall Street Journal reporter Evan Gershkovich was arrested in Russia and charged with espionage, an allegation he and the Journal said was absurd. The State Department declared that Gershkovich was “wrongfully detained,” an official status that commits the Biden administration to work for his release.

Journal publisher Almar Latour has played a key role in the legal and diplomatic effort to free Gershkovich. On this episode of Playbook Deep Dive, host and Playbook co-author Ryan Lizza talks with Latour to learn the inside story of this effort. 

They discuss: how the shadow of basketball star Brittney Griner’s detainment in Russia is influencing talks to bring Evan home; why a Russian hitman serving a life sentence in Germany may be the key to unlocking a deal with Putin; and how the 2024 election may affect Gershkovich’s fate.

Inside the WSJ’s ‘very intense’ effort to free Evan Gershkovich

The politics of the Israel-Hamas war have become one of the most divisive issues in the Democratic Party. Mark Mellman, the president of Democratic Majority of Israel – and a longtime pollster – joins host and Playbook co-author Ryan Lizza to get into the weeds on the new politics of Israel within the Democratic Party. 

Other subjects covered include the polling data behind Biden’s age, Trump’s hold on the GOP, double doubters, abortion, the fate of Nikki Haley voters, and whether you should bother paying attention to polls in the first place.

The new politics of Israel dividing Biden’s Democratic Party

TikTok, abortion, and IVF: three of the biggest issues in American politics right now and Kellyanne Conway is in the middle of all of them.  

Conway has been advising Donald Trump and Mike Pence for years and lately she’s best known for urging the GOP to leave TikTok alone and moderate the party’s message on reproductive rights.

On this episode of Deep Dive, host and Playbook co-author Ryan Lizza has a spirited conversation with Conway at POLITICO’s Health Care Summit, where they recorded Deep Dive’s first-ever live show.

How Trump could repeat 2016

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