Web Video: Discussing “The Hill to Die On” with Jake Sherman

ROBERT COSTA: Hello. I’m Robert Costa. Ever wonder how deals get done or in some cases derailed in President Trump’s Washington? Well, two top reporters have a new book that gives an illuminating look inside Congress at how key players jockey for influence and President Trump’s ear. One of them – Jake Sherman, co-author and co-editor of POLITICO ’s Playbook , a must-read newsletter – joins us tonight for this special edition of the Washington Week Extra. Jake wrote The Hill to Die On: The Battle for Congress and the Future of Trump’s America with his POLITICO colleague Anna Palmer.

Let’s start with a discussion of the Freedom Caucus, a conservative group that comes alive in this book. These days its leaders are close with the president, but as Jake and Anna write, quote, “Luckily for” Paul Ryan, then the House speaker, “the men in the Freedom Caucus were not the second coming of Lyndon Baines Johnson. They were outcasts – a bit insular, offbeat, and strange. Most of them hung out only with each other.” Jake, if you want to understand Trump’s Washington, you got to read The Hill to Die On , and you also have to understand the Freedom Caucus, which just is all over this book, as this force on the president’s shoulder. How did you get inside the Freedom Caucus, and what did it reveal to you about how this Washington with this president really worked?

JAKE SHERMAN: So our aim was to write a book about how Congress works and how, as you said at the top, deals either get done or don’t get done. I think the unique thing about our book is we met with sources, the main characters in our book and their top aides, over a two-and-a-half-year period. So we didn’t come to them at the end of a period and say take us through the last two years; we met with them weekly, having them – interviewing them for hours at a time as events were unfolding. So as the shutdown was unfolding, we were talking to them about what was going through their mind, what their emotions were, who they were talking to, so that was a useful aspect for this book. And also, as you note, we don’t come to the Hill as kind of Johnny-come-latelys. We’ve been – you and I and me and Anna have been up there for a very long time, and people see us around, and therefore hopefully trust us.

MR. COSTA: No, I always think about you, you’re just hanging out outside of the House of Representatives. You and I used to see Boehner come out when he was about to retire. But this Freedom Caucus, though, I mean, what is – explains their grip with President Trump?

MR. SHERMAN: I think the president sees them as the keepers of his creed, people who understand why he got elected, what the people who voted for him want. And I went to visit Jim Jordan at his house in Ohio, and Jordan describes the people in his district in central Ohio and what makes them tick and why Donald Trump was so appealing to them. He said these people are leaving their house and they’re seeing somebody drinking beer on their porch and not working, and they’re wondering why Washington is giving them money. This is the lens they see their constituents in and why they voted for Donald Trump.

And I also think that the interesting thing about the Freedom Caucus and President Trump is that President Trump gets loyalty from the Freedom Caucus, but when Nancy Pelosi was struggling for speaker Donald Trump was going to ask the Freedom Caucus to vote for Nancy Pelosi for speaker, which is a bizarre insight into a man who demands loyalty but doesn’t return it.

MR. COSTA: Another character that comes alive in this book is Paul Ryan, the former House speaker. He gets elected to Congress in his late 20s and then his life politically upended by President Trump, his whole election in 2016. Ryan seems to struggle throughout this book to just deal with it – to deal with the moment and his changing party.

MR. SHERMAN: I think this is a first draft of history reckoning with Paul Ryan, and we spent a lot of time thinking about Paul Ryan – I know you have too. But this is a guy who saw – his world got turned upside down when Donald Trump got elected. Paul Ryan was not for Donald Trump, and we have a chapter in the book called “Not a Trump Guy” which explains Paul Ryan’s hesitancy in backing Donald Trump, didn’t endorse him, really feuded with him on the campaign trail. But then when Donald Trump got elected he had two – he had a – he approached a fork in the road: he could either leave Congress and abandon kind of his life’s mission, which was passing conservative policy; or he could stay in government, try to use Donald Trump to achieve the ends he wanted to achieve. And also, something that’s fascinating, an insight into Paul Ryan: he thought that people wanted to see a normal person in government after Donald Trump was elected, which to me is a tremendous insight into the speaker. And we kind of chart the speaker’s power and his roller-coaster ride with Donald Trump, getting tax reform passed, but eventually leaving Congress because he was basically bone tired of the job, Paul Ryan was, and wanted to go spent more time with his family.

MR. COSTA: He got a tax cut through with President Trump, but he didn’t pursue deficit reduction in the way he always thought he would once he got power, once he became speaker or was a leader in the U.S. House. How will history look back on him? I know you’re writing the first draft of history, but he didn’t get a big budget deal passed that would lower the spending for Medicaid or Social Security. He dealt with President Trump in a way that was somewhat pained. What’s your read on history’s read?

MR. SHERMAN: So I think a lot of people believe he was intellectually dishonest and believe that spent his career talking about the deficit, finally had an all-Republican Washington, and completely abandoned it. We have an amazing scene in the book of Paul Ryan and Donald Trump getting together before election day to try to make peace, basically, a meeting that was brokered by the Republican National Committee. And Paul Ryan has these charts and is talking about Medicare spending, and deficit reduction. And Donald Trump looks at him and says: I know you like that, but I think that’s stupid. Which was a real sign to the speaker that it wasn’t worth his time. And I’ll let other people judge what that means about Paul Ryan, but it’s something he spent literally no time on in Donald Trump’s Washington.

MR. COSTA: Those kind of frank conversations are all over The Hill to Die On . One passage in the book describes a scene where the late Senator John McCain of Arizona is explaining military reform to President Trump’s son-in-law and advisor Jared Kushner early on in the administration. Here’s the scene, “Don’t worry, Senator McCain. We’re going to change the way the entire government works, Jared Kushner said, without a hint of irony. Good luck, son, McCain responded.” What a scene about Mr. Kushner, about someone who came with President Trump to Washington, but official Washington was not too impressed.

MR. SHERMAN: No, Jared Kushner was successful as a real estate investor in New York, primarily using his father’s money. His father was a very wealthy investor himself. Jared has struggles in Washington, and not outwardly, but tries to bend Washington to his will, unsuccessfully. He also told Paul Ryan and a group of Republicans – some of Paul Ryan’s aides, rather – that he didn’t like the committee process, and he would fix that later; basically saying he would refashion Congress, which is a 200-something-year-old institution.

He also says: Why is the government spending so much money on undocumented kids? We could just put them up at the Four Seasons for that price. Of course, putting up undocumented kids at a five-star hotel is something that doesn’t comport with the reality as we know it. So somebody who came to Washington and thought he would be able to do what he’s done his whole career, which is be successful on his own kind of charm and merits and was not able to do that.

MR. COSTA: One of the other major characters is Speaker Pelosi. She now – she’s minority leader throughout most of the book, then she wins the speakership in November 2018. One person who comments on her is President Trump in an Oval Office interview with you and Anna Palmer. He says he’s impressed with her ability to hold together the Democratic Party.

MR. SHERMAN: He says: Democrats are lousy on policy, lousy on politics, and have the worst ideas in the world, but they stick together. And I think, and I’m playing armchair psychiatrist here – (laughs) –

MR. COSTA: Careful.

MR. SHERMAN: I think the president – I think the president looks at Pelosi and sees somebody who keeps her troops together and wonders why he didn’t have somebody like that as speaker of the House. And I think he’s jealous of that. And he told me basically that. And he says, listen, I like Pelosi. He had obviously dealt with Pelosi, as he calls it, in his developer life, his business life. And he was a donor to Chuck Schumer and a friend of Nancy Pelosi’s. So there’s a history there more than meets the eye.

MR. COSTA: This is a little bit of an insider question, but you and I cover these guys and these women on Capitol Hill. Kevin McCarthy, the minority leader, not someone who’s very well-known nationally. But he now runs the House GOP. He is someone who has really aligned himself in a comfortable way with President Trump, far different than House Speaker Ryan handled the president. What’s McCarthy’s future based on all of your reporting?

MR. SHERMAN: He’s the top Republican now, so that’s a pretty good perch for him. He was never the top Republican before. There was always somebody else above him. Listen, if he’s able to bring Republicans back to the majority in 2020, he will probably be speaker of the House. I’m not sure he lasts until 2022. He got elected in 2006 – or – 2006, right. And so he’s not long – he wants to – he always thinks about when he could make some money, when he could go out into the private sector. He’s not obsessed with striking it big or becoming rich, but he is fascinated by innovation and wants to do something different than just be a politician his whole life. So tough to say what his future is, to be honest with you.

MR. COSTA: And I have to ask one final question, the great Anna Palmer, a friend of both of ours, after writing a book together, still friends, still good colleagues, or not?

MR. SHERMAN: Yes, we are. (Laughs.) We’re still friends, still colleagues. I couldn’t have done it without her. We did it together. It was a real partnership. Writing a book, a 400-page book, while doing a full-time job is not easy. So I’m glad I had someone to help me.

MR. COSTA: Four hundred pages. It’s about the length of the Mueller report, but this book, it does not have redactions. (Laughter.)

That’s it for this week’s edition of the Washington Week Extra. You can listen wherever you get your podcasts or watch on the Washington Week website. I’m Robert Costa. See you next time.