President Trump's signature legislation, the One Big Beautiful Bill Act, is crawling its way through Congress. Having passed the House by a single vote, the so-called BBB is in the Senate where various Republican factions - the fiscal hawks, the centrists, the populists - are divided over how to resolve their many competing priorities over the national debt, Medicaid, and tax cuts to name a few.

What's driving these ideological differences among Senate and House Republicans? What role has Trump played and will he play in continuing to lobby Congress? And will the BBB move fast enough to be on President Trump’s desk by July fourth? (Spoiler alert: it will not.)

Amy put all these questions to Leigh Ann Caldwell, chief Washington correspondent for Puck.

A quick note: we recorded this conversation on Wednesday, June 4th, as the Elon Musk and President Trump breakup was beginning, but before it burst into the full view. And it appears the falling out has been driven, at least in part, over Musk's opposition to the Big Beautiful Bill. But as Amy has said, she doesn't believe this changes the calculus for Congressional Republicans.

You can watch part of the conversation our YouTube channel: https://www.youtube.com/@thecookpoliticalreport

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When we booked this episode with Pod Save America co-host Dan Pfeiffer several weeks back, our plan was to talk about the Democrats and their strategy and messaging around Trump - something Dan's been writing about for his Substack, Message Box.

Should Democrats just focus on the economy? Should they raise alarm bells over deportations? How loudly and strongly should they push back against Trump?

And we do discuss that, but as it turned out, there was a lot more to talk about with Dan. For one, as a former Obama senior adviser, Amy wanted to ask his thoughts on the new reporting coming out about Joe Biden's health and how his inner circle worked to conceal it.

In addition to that, we received an important report from the data firm Catalist about 2024 voters, shedding more light on why Kamala Harris lost and Donald Trump won. As a fellow data nerd, I knew Dan would be ready to dive into it.

We recorded this on Wednesday, May 21st.

You can watch our entire conversation on our YouTube channel.

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Rahm Emanuel has held many titles: Congressman from Illinois, DCCC Chairman, Chief of Staff to Barack Obama, Mayor of Chicago, and Ambassador to Japan under President Biden.

These days, he doesn't have an official position at the moment. But that's not stopping him from giving some very pointed advice to Democrats on every possible platform: cable TV, political shows, podcasts, late night TV, and different political conferences.

So how does Rahm Emanuel think Democrats should be responding to Trump 2.0? How does the party recover from 2024 and prepare for 2028? What does a successful midterm strategy look like in 2026? And given his own, let's say, active media schedule, what are his own plans for the future?

He came on to talk to Amy about all that.

We recorded this conversation on Wednesday, May 14th.

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You may know our guest today, Josh Holmes, as one of the hosts of the popular political podcast, Ruthless.

For those of you who don't know, Ruthless is to the conservative media sphere as Pod Save America is to the liberal media ecosystem.

But long before he started his podcasting gig, Amy knew Josh as a Republican political operative.

He was chief of staff to Mitch McConnell and ran his 2014 re-election campaign. He also had a stint at the National Republican Senate Committee.

He now runs the public affairs firm, Cavalry, and he's still actively giving advice to Republican candidates.

Josh's two roles as a member of the new media and a seasoned Republican political hand gives him unique perspective into our current political era.

This conversation spans a similar gamut from what advice he'd give to down ballot Republicans for the upcoming midterms to his thoughts on the Trump tariff endgame. Josh also talks about how candidates can best navigate the new media landscape.

We recorded this conversation on Wednesday, May 7th.

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We are 100 days into the second Trump administration and there's no better person to help us understand what voters are making of these first months of Trump 2.0 than Republican pollster Kristen Soltis Anderson.

Kristen is a founding partner of Echelon Insights, an opinion research and analytics firm. She's a contributing opinion writer for The New York Times and an on air political contributor at CNN.

Quick disclaimer: we taped this conversation on Thursday, April 24th, before the flurry of 100 day polls were released this past weekend. That's why you won't hear us asking her about these polls.

But the reason we wanted to have Kristen on in the first place was that we didn't want to get caught up in the immediate set of data. We wanted Kristen to do what she does best which is to filter the signal from the noise, present a 30,000 view of the political environment rather than focusing on the minutiae or just small movements in data. What we like about Kristen so much is that she's able to to toggle seamlessly between reading cross tabs but also probing voters in focus groups and really listening to what they are saying or not saying, and then explaining it to regular people in a way that is approachable but not condescending.

That's why we were especially excited to talk with her about a presidency as complicated and unprecedented as Trump's.

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Way back in the late 1990s, Cook Political Report founder Charlie Cook had an idea to rank all 435 congressional districts by their partisanship - in other words, whether a district is more Republican or more Democratic.

That way, we'd be able to see, at a quick glance, which members of Congress represented districts that were either slightly or strongly partisan. For example, is a certain Republican representative in a very solid Republican seat…. or in one that is only slightly red… or even one that was blue or blue leaning?

Thus was born the Cook PVI, which stands for Partisan Voting Index. And since 1998, CPR has released a new addition every two years.

This admittedly very geeky undertaking is also something we get really excited about because it cannot only tell us the partisanship of every district, but with more than 25 years of data, we can see how districts have shifted over the years.

The person behind the Cook PVI and how it all works is David Wasserman, The Cook Political Report’s senior editor and elections analyst.

We invited him on to explain what the Cook PVI is, how we calculate it, what we learned from it for 2025, and what it may tell us about elections in 2026.

We recorded this conversation on Wednesday, April 9th.

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Read Dave’s Cook PVI analysis: https://www.cookpolitical.com/cook-pvi/introducing-2025-cook-partisan-voting-index-slightly-depolarizing-election

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On the last podcast, Amy talked with Chauncey McLean, head of the Democratic super PAC Future Forward, about their media strategy for Kamala Harris and why things didn't work out as they had hoped.

For this podcast, we turn to the ad strategy of the Trump campaign with John Brabender, the chief creative officer for the media company BrabenderCox.

John was hired as Trump's ad consultant in early 2023 and worked with him throughout the entire campaign. He had incredible access to and input from Donald Trump about the ad making process and strategy, which he shares with us here in colorful detail - like what it's like to work on the Trump campaign and, specifically, to work with the president when putting these messages and ads together.

We also wanted to talk to John about whether the lessons he learned working for Trump could translate to non-Trump candidates and Republican downballot candidates who have to run in the 2026 midterms.

This conversation was recorded on Wednesday, April 2nd.

Back in the 2012 cycle, Chauncey McLean was a young staffer on the Obama campaign working in the newly developing field of data analytics.

Six years later, McLean put those data science skills - and the ones he developed while working in the private sector testing ads for commercial products - to work as head of the Democratic super PAC, Future Forward.

Most outside super PACs like these do an extensive amount of polling and survey work and bring in multiple outside advisers to help manage and produce campaign ads and other material.

What makes Future Forward unique is the tremendous amount of survey data and ad testing that they do. Its team of data scientists surveyed millions of voters and tested thousands of ads with the goal of finding and airing the ads that moved the needle the most with the voters.

During 2024, the group poured more than $600 million dollars into ads that supported first Joe Biden and then Kamala Harris' campaign for president.

At the end of the day, the Trump campaign's advertising and media strategy was more successful, particularly his ability to connect with younger men via social media platforms like podcasts and YouTube.

As the Democratic party struggles to find its footing, we wanted to talk to Chauncey McLean about what he learned from Harris' loss and how Democratic groups like his are adapting to this fractured media environment going forward.

We recorded the conversation on Wednesday, March 19th.

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We've been wanting to have Terrence Woodbury on the podcast for a long time.

The reason is that he's a pollster who has done some amazing work with demographic groups that made a big difference in the presidential race last year, but also in previous cycles: Black voters, voters of color, and younger voters.

And if many Democrats were surprised by the erosion in support among what they thought was a reliable Democratic base, Terrence has been observing this slide for years -- particularly among men of color, a group he calls the new swing voter. As a pollster to the Kamala Harris campaign, he and his company HIT Strategies, had a front row seat to how voters felt about Harris, Donald Trump, and the Democratic party as a whole.

So we wanted to ask Terrance to discuss the results of the 2024 election, but also look forward to what he's hearing now from voters with Donald Trump in office and what he thinks the Democratic response should be to the Trump era.

Terrence Woodbury is cofounder and president of HIT Strategies which is a public opinion research firm.

We recorded this conversation on Wednesday, March 12.

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Last year, as March Madness kicked into gear, there was one athlete everyone seemed to be talking about: Caitlin Clark. The then University of Iowa guard was on her way to leading her team to the NCAA finals, selling out stadiums everywhere she went and creating an unprecedented level of excitement around women's basketball. This interest followed her to the WNBA when she signed with the Indiana Fever.

Our guest, USA Today sports columnist Christine Brennan, is writing a book about Caitlin Clark called On Her Game, which tells the story of Clark's rise to become the most famous female team sport athlete in history.

Christine has been a long-time chronicler and advocate for women in sports. She's also deeply interested in politics and has a keen understanding and appreciation for how sports and politics intersect.

We wanted to have Christine on to help tell the story of how laws like Title IX helped pave the way for a phenom like Caitlin Clark. And we also wanted Christine to reflect on where we are today when it comes to politics, sports and gender.

These three topics have always been intertwined in our culture, but the Trump era has brought it to a different level. In Trump’s first few weeks in office alone he appeared at the Super Bowl and signed an executive order banning transgender athletes from competing in women’s athletics. We also had Canadians booing the U.S. national anthem at an international hockey game in response to Trump's tariff threats as well as his references to annexing our northern neighbor.

Christine Brennan is an award-winning national sports columnist for USA Today. She's a commentator for CNN, ABC News, and PBS NewsHour. Her book about Caitlin Clark is available right now for preorder on Amazon. It will be available wherever books are sold in early July.

Pre-order Christine Brennan's book: https://www.amazon.com/Her-Game-Caitlin-Revolution-Womens/dp/1668090198

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