The Inside Story of Trump’s First 2 Years in Washington

Jake Sherman, senior writer at Politico and co-author of Politico Playbook, is the co-author with Anna Palmer of the new book “The Hill to Die On: The Battle for Congress and the Future of Trump’s America.” The Daily Signal spoke to Sherman about the book and the ways President Donald Trump has transformed Washington. Our full interview is below along with a lightly edited transcript.

Rob Bluey: Congratulations on the success of your book. It’s already a New York Times best-seller. You and Anna have done a remarkable job of chronicling the first two years of Trump’s presidency and the battles that have taken place in Congress. Tell us why you decided to write it.

Sherman: We were approached to write a book about Congress at the beginning of 2017. Anna and I had thought about this many times over the years. We thought about whether we can write an interesting book about Congress. We’ve always been convinced that Congress has the best story in the world. And we think it’s the best story in politics even more than the White House.

When Trump got elected, we had a sense that it would be very interesting because it was clear he was going to not conduct himself as a typical and ordinary president. That’s been clear now, it was not clear to the extent to which he would be able to do that in 2017. We figured how the deals got done, or didn’t get done, would be a fascinating story.

We started, basically, with Election Day 2016, ended with the shutdown, which was not planned, obviously, at the beginning of 2019. And we told the story, not as a Trump story solely, but as a story about Paul Ryan, Kevin McCarthy, Mitch McConnell, Nancy Pelosi, and the Freedom Caucus. The trials and travails and ups and down contained within those characters. We took a different tact, which was to not focus maniacally on Trump, as a lot of books have done, but through Congress’ eyes.

Virginia Allen: Based on your reporting, what are some of the biggest changes that you’ve observed in Washington during Trump’s presidency?

Sherman: A few things. It’s a good question. A few things. No. 1, I think—and this is not a major theme of the book, but it came up time and time again—the role of cable news in the Trump administration in shaping both his view and the policies that he supports.

We have several instances throughout the book, where Sean Hannity of Fox News was acting as an informal adviser, both to the president and to Republicans on Capitol Hill. That’s basically unheard of. I’m not saying it’s criminal or anything, it’s just not typical for another administration in other time. That’s probably one of the big ways things have changed.

Also, as it’s been reported a million times, the extent to which the president is talking to just many, many, many people all the time is fascinating. Imagine if you’re CEO of a company, and you’re calling up dozens of people before you make a decision throughout the company, and that’s kind of what the president does. I think those two are the major changes.

One thing that I’ve observed second hand since the book has been released is mostly in places like New York and L.A. and on the coast, people always ask me, “Are Republicans going to be happy when he’s gone?”

The thing that I and your listeners might sympathize with this, the thing that I don’t think a lot of people understand is that there’s a whole country besides the coast, where the president is exceedingly popular, and that’s reflected on Capitol Hill, or at least was between 2016 and 2018.

This is not a Trump fan book. It’s not a Trump hate book. And there’s been a lot of those two things. …

Bluey: We certainly appreciate that reporting that you’ve done. Robert Novak is one of the people who I looked to when I was getting my start in reporting. I love the fact that he was able to bring that insight much the same way that you and Anna do in Playbook every day, and you do as well in this book.

One of the things that you write is that during those first two years of the Trump administration, Congress gained power, but you say shrank in its willingness to exercise it. How do you see that changing now that Democrats control the House? Is there a greater appreciation for Congress’ Article 1 responsibility today?

Sherman: I would say a few things. What we meant by that is Congress gained in power because there was a president who didn’t really understand Washington, or government really. … It’s not me saying that, that people like Mitch McConnell told me he basically didn’t know how Washington worked in any way, shape, or form—which, by the way, allowed McConnell to reshape the judiciary.

But when we say shrank in its willingness to use it, at times, it has the opportunity to, for example, shore up Robert Mueller’s investigation. It did not do that. But going forward, I think it’s quite clear that the legislative branch and the oversight responsibilities and powers that Congress has are going to be used more than ever. We see that.

We see now that the Democrats are considering using penalties, fiscal penalties, monetary penalties for people who don’t testify to their liking or fork over documents. I think we’re about to see a major sea change in Congress’ power and how it used it. I would say the president vastly, as my reporting would show, vastly underestimated how bad a Democratic House would be for him.

He told us in an interview in the Oval Office, Republicans were too nitpicky when it came to controlling the house. They had too many changes to legislation, he didn’t appreciate that. Now, he has a Democratic council who he thought that he would be able to work with based on his relationship with Chuck Schumer and Nancy Pelosi, and he finds itself under a barrage of very serious investigation. I don’t think he anticipated that.

Allen: You write about the government shutdown in the book, how that happened and the fallout. In both cases, President Trump squared off against Speaker Nancy Pelosi and Sen. Chuck Schumer. What did you learn about their relationship? Is there any chance of them working together on legislation?

Sherman: I would say I learned a lot. I was eager to learn a lot because it’s a very unique relationship. Let me start backward, kind of.

In 2017, the president, as many of your listeners will remember, cut a deal with Chuck Schumer and Nancy Pelosi to keep the government open in place of cutting a deal with Paul Ryan and Mitch McConnell, who had a different view. We make the case in the book that that deal that he cut to keep the government open for three months—lift the debt ceiling for three months and provide disaster relief for places like Texas—led to a lot of the border squabbling that we saw over the years.

I think the president appreciates the flare he gets, the coverage he gets for cutting deals with Democrats, No. 1. No. 2, he has a reverence for Nancy Pelosi that he does not have or did not have for Paul Ryan, I would say for sure.

He doesn’t understand why Democrats stick together so much better than Republicans. He said as much to us on the record that Democrats stink with their policies, they’re bad politicians, but they stick together and Republicans do not.

He likes Pelosi. He actually had planned to convince the Freedom Caucus to support Nancy Pelosi for speaker if she fell short with Republicans, which is a stunning statement and a lot of your listeners will appreciate that. That’s unheard of. The Republicans have spent hundreds of millions of dollars trying to prevent Nancy Pelosi from taking back the majority.

… I was optimistic that he would cut deals with Democrats, I had been in 2016. I don’t believe right now there’s the climate to do so for many reasons. Chief among them that the president is exercising his power, and we’ll see how much power he’s able to exercise in preventing Democrats from talking to members of his administration and getting documents that they deem pertinent. That is going to be a huge battle both legislatively, politically, and legally—I would imagine.

I would imagine that the cost of Nancy Pelosi
trying to cut deals with Donald Trump goes up exponentially if he’s unable and
unwilling to participate in oversight in his administration.

Bluey: I want to follow up on that in my next question. Much of the tension with Democrats over those two years has centered on immigration and border security. We’re now hearing that Jared Kushner, who’s referenced throughout the book, is working on a plan.

How much influence does Kushner have with the president? Do you see any potential for him to repeat the success that they had with criminal justice reform on an issue like immigration?

Sherman: Rob, as you know, Republicans have been for criminal justice reform for many years. You’ll remember Paul Ryan in late 2016 had a deal basically cut with Barack Obama to do something similar in criminal justice reform.

A lot of Republicans and Democrats believe Jared’s prowess when it came to criminal justice reform was a little bit overstated. Because he convinced Republicans to do something that Republicans were already willing to do. That’s No. 1.

No. 2, Jared obviously has huge influence with the president. He’s the son in law, trusted adviser, from what we could see. Jared also doesn’t really, in my reporting, and according to Republicans who were in the room with him, does not really grasp the issues on immigration reform as he would need to to cut a deal. That’s not my assessment. Republicans who he’s worked with, that’s their assessment.

He, in the beginning of the shutdown, said, “I’ll be able to quickly solve this.” And then proceeded to convince the president to negotiate with Democrats and, of course, he negotiated with Democrats and he had to declare a national emergency. He’s not as savvy as maybe he thinks he is when it comes to immigration reform.

I would say, there are two sides to this issue. We make the argument in the book that Democrats were completely disingenuous when it came to the border walls and opposed it because it was Donald Trump’s border wall.

Democrats had approved the border wall many times before in different forms, but Donald Trump made the border wall about himself. Democrats were then incentivized to oppose it. That’s kind of how it went at the beginning of this year.

I’m skeptical—I’m a skeptic because I’m a reporter—that reform will happen. I think the two sides, frankly, just have way different views on immigration reform. Jared Kushner is not going to bridge those gaps, which are basically defining gaps between the two parties at this point. I’m skeptical that he’ll be able to do that.

Allen: You had the opportunity to speak with the president. What insight did you gain from talking to President Trump directly? Given his hostility toward the press, what is he like one on one?

Sherman: I think his hostility toward the press is obviously disappointing to members of the press, but he’s still … We see he just spoke to The Washington Post, Bob Costa for a story about oversight of his administration. He speaks to reporters all the time.

Obviously, he sees it politically expedient or politically benefiting him to stoke a war with the press. But that’s his choice. It’s disappointing because we live in a country where freedom of the press is of such huge importance and such a defining characteristic of our country.

It’s a little bit befuddling to me why he does that. But that’s that. I thought he was a lot more engaged in the kind of rough and tumble of D.C. politics than I expected.

I don’t mean that I didn’t expect him to be engaged in politics. He’s obviously the president because he’s a pretty good politician. But I didn’t anticipate that he would understand the characters and the palace intrigue as he did with the tension between Jim Jordan and Kevin McCarthy or Nancy Pelosi’s inability or her quest to become speaker again. All of those things were really interesting to me, how he was very tuned into those dynamics.

He’s a friendly guy who I would say enjoys, basically, my assessment was he would be talking to the press all the time if it were up to him. Obviously, he has gripes with the covers, but so does every president. Nothing to do with that. Those are my general impressions of dealing with him.

Politico’s Jake Sherman with Rep. Jim Jordan, R-Ohio, in the Capitol as Congress worked to avert a partial government shutdown on Dec. 21, 2018. (Photo: Tom Williams/CQ Roll Call)

Bluey: Now, Jake, from our own reporting at The Daily Signal, we know what a whirlwind it has been since President Trump was elected in November 2016. As you reveal in the book, there’s been quite a bit of tension between the conservative House Freedom Caucus and Republicans in leadership and Congress.

Based on your reporting, who has a bigger influence on President Trump today? Is it someone like a congressman, Mark Meadows or Jim Jordan, who lead that Freedom Caucus? Or the Republican leadership of Kevin McCarthy and Mitch McConnell?

Sherman: We have an interesting dynamic now because in the last Congress, Meadows and Jordan were oiled to Paul Ryan and disagreed with him on a lot. In the end, the president sided with Meadows and Jordan, which led to a government shutdown over immigration.

Now, he has a lot of trust in Kevin McCarthy. Kevin McCarthy is a close ally of him. As are Mark Meadows and Jim Jordan. I think the relationship between Meadows and the president is no longer as important as it once was because the Republicans are out of the majority.

But for those two years, between 2016 and 2018, the House Freedom Caucus, the 20 or so members, depending on the issue of the House Freedom Caucus, were the most important people in Washington and perhaps some of the most important people in the country because they had veto power over any legislative issue.

But today, I would argue that McCarthy and McConnell have a little bit more sway than Jordan and Meadows. Jordan and Meadows do play an important role though. They are the president’s defenders on the judiciary and oversight committee, and that’s incredibly important.

Allen: You’ve mentioned the
influence that Sean Hannity wields with President Trump. Who else like him is
influencing the president behind the scenes?

Sherman: Well, there’s nobody who’s quite like Hannity, based on my reporting. We have a couple of instances in the book, and I’ll mention two of them. He was on a conference call on health care reform, Sean Hannity was with Paul Ryan and Mark Meadows. We’ve never seen something like that before, or at least not in my experience. That’s incredibly odd.

I know, because I was there, that Sean Hannity was talking to members of the Freedom Caucus during the government shutdown, and they were swapping ideas, swapping strategy. That’s very, very unusual.

I can’t remember, and forgive me if I’m wrong, but I can’t remember Rachel Maddow on the phone with President Obama during health care reform or anything like that. Perhaps it was happening and we missed it.

But I would say there’s no parallel to Sean Hannity. Maybe Lou Dobbs, who the president obviously appreciates his views on immigration and other things of that nature. But Sean Hannity is really a singular figure for President Trump.

Bluey: Finally, you’ve been reporting on Capitol Hill now for 10 years, and you’re also an NBC and MSNBC contributor. You’ve earned a lot of respect and credibility for the work and reporting that you’ve done. What is your advice to those who are getting their start in journalism today?

Sherman: I work hard because there’s nothing really that replaces hard work. I would say a few things. I would say, and I’m guilty of this, too, don’t spend too much time on Twitter because it’s a pretty poisonous place. But I would also say that there’s really no plus if you’re an even reporter for a news outlet, there’s no plus in picking sides. There really isn’t.

My entire career has been covering House Republicans. The media’s viewed as liberal. My job is not to choose sides. My job is to adequately and accurately reflect what the views are of the people I’m covering and inject skepticism where necessary.

But there’s no reason to be a partisan in a nonpartisan environment. It’s just not worth it. If you can’t get both sides to talk to you, you don’t have much going in this business.

I would say, be there all the time. I spend 12 to 14 hours a day in the Capitol, and that’s how people get to know you, and people get to trust you when you’re talking to them, when you don’t need something. That would be my top-line advice.

Bluey: That is really great advice. I think that it’s something that is certainly a lost art as reporters today look for easier ways to go about getting stories, but there’s nothing better than showing up, being there in person, talking to people directly, face to face.

Sherman: Thanks, Rob. Appreciate it.

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