When you look at the major diplomatic events of the last thirty years, Derek Chollet has experienced them all. He’s worked with legends like James Baker, Strobe Talbott and Richard Holbrooke and served in some of the highest echelons of the White House, the Pentagon and the U.S. Department of State. From Bosnia to Syria — and now Russia — Chollet has helped to shape America’s approaches to its policy abroad.

Today, Playbook co-author Ryan Lizza sits down with Chollet, who’s currently the Counselor of the Department of State, to dig into Foggy Bottom’s approach to helping Ukraine and handling Putin.

'It's war and the enemy gets a vote’: The man advising Blinken

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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The biggest movie in the country right now is about a civil war — in America.

If you see the film “Civil War” at a theater in downtown Washington, the scenes of the Lincoln Memorial exploding and the White House being attacked are jarring when you exit into the D.C. air. 

The movie is writer and director Alex Garland’s very in-your-face attempt to imagine the unimaginable in America — an authoritarian leader in the White House, intractable political differences being resolved through violence and the very specific horrors of modern warfare — urban fighting, refugee camps, mass atrocities, the collapse of the currency — all the things that we associate with stuff that can happen over there happening right here in the United States.

“Civil War” is also a movie about journalism.

It follows four reporters traveling from New York to Washington, D.C., via a circuitous route through Pennsylvania, West Virginia and Virginia. 

The movie takes on a lot of the weighty issues we talk about on shows like this one: media ethics, political polarization, disinformation polluting our media ecosystem and the potential threat from an autocratic leader.

Wagner Moura plays a hardened war correspondent addicted to the battlefield. He also provides some much needed levity in the movie.

Moura is best-known for his role as Pablo Escobar in “Narcos.” But he’s also a former journalist, a political activist and a writer and director himself. His 2019 movie “Marighella” about the coup and counter-revolution in Brazil in the 1960s incurred the wrath of then-president Jair Bolsonaro in Moura’s home country of Brazil. 

Deep Dive host and Playbook co-author Ryan Lizza talked with Moura on Thursday just as Washington’s annual White House Correspondents’ Association Dinner festivities were getting under way. It’s the time of year when the relationship between journalists, politicians and Hollywood is at its peak in this town. 

They had a fascinating conversation about how making a movie about a new civil war changed Moura’s own personal thinking about politics, how his experience with Bolsonaro in Brazil is a warning for Americans and the role of art in politics.

“The truth as we know it is over.” “Civil War” star on how it really could happen here.

After months of delay, this week House Speaker Mike Johnson advanced his much awaited version of the Ukraine, Israel, and Taiwan foreign aid package.

Standing between that legislation and the House floor: two very powerful committees. 
First, the House Appropriations Committee, which controls about a third of federal spending. And second, the Rules Committee, which controls access to the House floor, and which has become a problem for GOP leaders in this Congress.

Johnson needed to pick the lock on both of these committees. And there is one Member of Congress who has chaired them both. Not just in the past year — but in the past month: Oklahoma Republican Tom Cole.

Deep Dive host and Playbook co-author Ryan Lizza caught up with Cole on Thursday afternoon after he’d just testified in support of the foreign aid bill in front of his old committee. 

They got deep into the weeds of why the Rules Committee has been such a trouble spot for recent GOP speakers; and they discussed Johnson’s tenure so far and whether Cole thinks the Speaker can hang on as members threaten to oust him. 

Cole also previewed how he will run the Appropriations Committee, including how he’ll handle the controversial earmarks process. And Cole answered some prying questions from some of his favorite historians on the subject of Donald Trump.

Rep. Tom Cole’s cigar diplomacy to secure Ukraine, Israel, and Taiwan aid

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.

'It's war and the enemy gets a vote’: The man advising Blinken

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