New Lobbyists Arrive In Washington, Cashing In On Their Connection to Trump | KERA News

New Lobbyists Arrive In Washington, Cashing In On Their Connection to Trump

Sep 28, 2017
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TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. The Trump presidency has changed how things work in Washington. My guest, Nicholas Confessore, writes that in spite of the president's promise to drain the swamp, the new administration has actually spawned a new breed of lobbyist. Close to 20 of Trump's aides, friends and hangers-on have made their way into the Washington influence business. And the president appointed more than 100 lobbyists to jobs at the EPA, the Interior Department, the FCC and elsewhere.

Confessore's article "How To Get Rich In Trump's Washington" was in a recent issue of The New York Times Magazine where he's a writer at large. Confessore also covers the intersection of wealth, power and influence for the newspaper. Since the election, he's written about how the Trump inauguration drew twice as much money as any previous inauguration, how the prerequisite for key White House jobs has been loyalty, not experience, and how the wealthy members of Mar-a-Lago have a level of access to the president that might elude even the best-connected lobbyists.

Nicholas Confessore, welcome back to FRESH AIR. You know, although one of President Trump's slogans is drain the swamp, you write that the dysfunction within the Trump administration has actually made lobbying more essential. Would you explain that seeming paradox?

NICHOLAS CONFESSORE: Well, I think what's happened is that Trump has created more uncertainty than ever in Washington. And when you combine that with the fact that he was genuinely kind of unknown to the permanent class in Washington, that the lobbyists and the people in D.C. hadn't really forged connections to him before he became president, you can imagine that the uncertainty combining with not knowing who to call or having relationships in the White House in the Trump administration would actually make the few lobbyists who did know what they were doing and who to call extremely important in Trump's Washington.

GROSS: But you're right. Another problem with the Trump administration now, it's not just a question of knowing who to call. There's often nobody to call because the administration is so understaffed and so are so many of the agencies.

CONFESSORE: That's right. I think you have to think of this as a couple of kind of interwoven problems. The Trump administration has been so slow at staffing itself, at filling the ranks of the upper appointive jobs in the bureaucracy, that many desks in places like treasury are empty or filled with temporary people. So there actually isn't anybody at the wheel throughout the bureaucracy who's there to carry out the president's instructions. So you have a vacuum. Then in the White House in the West Wing, you have a power fight. You have factionalism that we haven't really seen on this level in a very long time. People are battling over the president's ear, competing with vastly different visions of what Trumpism is and who it represents.

But essentially, when you have a president who likes to encourage infighting on his staff and isn't sure of his own mind on a lot of policy positions of his own and hasn't created a disciplined policy process to create output from the White House, you combine that with the lack of representation in staffing at the agencies and you have huge amounts of uncertainty throughout Washington. And chaos is always good for lobbying in Washington.

GROSS: Why is chaos good for lobbying and how are lobbyists - how are the old-school lobbyists dealing with all this uncertainty and infighting within the Trump administration?

CONFESSORE: The answer to this changed over time, so I'm going to start a bit at the beginning. When Trump first came in, corporate CEOs, trade associations in Washington, the people who companies hire to run their Washington offices, just didn't know what to expect. Is Trump going to govern as a nationalist or a New York real estate guy? How serious is he about the trade stuff? So early on, you had this real scramble. The established Washington firms were hiring people as fast as they could who had Trump connections. If you had a Trump connection and wanted to be a lobbyist, you could write your own ticket. They were calling guys like Corey Lewandowski, who was a fired Trump campaign manager, who co-founded a lobbying firm, a new lobbying firm. And CEOs would call them to say how should I handle a meeting with the president? Or what happens if the president starts dumping on my company on Twitter?

But the established firms were also trying to hire Trump people, and so they did. And by March or so, you had about 20 people with Trump connections who had worked on the campaign or were attached to it in some capacity all of a sudden in business on K Street. And they were really desperate to understand what was actually happening in the White House, what to believe, what to ignore or what to disregard, trying to get a handle on what the policy product of the White House was going to be.

And that sounds like an anodyne way to put it, but just think about how important process is in Washington. People were used to understanding how the process worked. There were people on K Street, lobbyists, who had spent years mastering the intricacies of regulation and the legislative calendar, and it was a kind of a ballet. And if you knew how that ballet worked, you could sell that expertise to your corporate clients or to other clients.

GROSS: So what have you been hearing about the kind of favors that are being traded?

CONFESSORE: Well...

GROSS: You've actually heard examples of that, right?

CONFESSORE: That's right. So one example, Lockheed Martin - you know, as you may recall, your listeners may recall - when Trump was first coming into office, he was very critical of the fighter jet program that Lockheed is doing for the U.S. And he kept saying it was too expensive - the F-35 fighter jet program. And he really bashed them. And such was the president's megaphone - and the president-elect's megaphone before that - that he actually dropped their stock price. He cost them billions of dollars in market cap. And this continued for a while. And so what'd they do? Well, Lockheed Martin brought in Corey Lewandowski and his partner for advice.

GROSS: Corey Lewandowski, former campaign manager for president...

CONFESSORE: Exactly.

GROSS: For candidate Trump.

CONFESSORE: And a newly minted K Street lobbyist, or at least a newly minted partner in a lobbying firm since he doesn't register as a lobbyist. And they asked for his advice, and they said, look, it's transactional. Be very simple. Don't, you know, come in with a ton of charts and briefings. Just come in with a transaction. And so what happened after that? Well, the chief executive of Lockheed went to her next meeting with Trump and said we're going to expand this plan. We're going to cut the price on the F-35 and we're going to say it's all because of you. And pretty soon, Trump was out there praising Lockheed Martin, and the criticism stopped. So right there you have an example of how the rules of power changed in Washington under Trump.

GROSS: You write that one person offered Corey Lewandowski $250,000 to get the president to tweet about him, or was it about his company, but did that work out?

CONFESSORE: Yeah, so one thing I wrote about in my story was the crazy things people were offering to pay money for when Trump came into office. It was almost like open season. People were going to lobbyists and saying I'll give you half a million dollars if you can get me an ambassadorship. They said to Corey Lewandowski, I'll pay you a quarter million if you can get the president to tweet about me. And according to Corey Lewandowski, that deal didn't go through. He didn't accept it. This is an example of things they were turning down. But it shows you the kind of free for all and it also shows something else that I think is really important. I think your average person thinks, oh, a picture with the president is a picture. That's fine. But you don't understand how valuable that picture with the president is to some people.

If you're a businessman, especially one in a foreign country, and you have a picture of yourself with President Trump in your office, it sends a signal to your clients and people that you're doing business with that you were connected at the highest level of world power. People actually really take those cues and it matters, and that's why someone's willing to pay hundreds of thousands of dollars to get a photo if they can get one.

GROSS: You know, some people say that President Trump isn't very interested in policy. He wants wins. He wants to win, and he wants to be seen as strong. So is that affecting lobbying, this emphasis on winning as opposed to an emphasis on actually believing in the importance of certain policies or having a deep understanding of policies?

CONFESSORE: You know, I think it does. I think that his lack of interest in the details of policy and his inability to focus on all but a couple of ideas like immigration and the wall make it hard for his administration to move big initiatives. It's why they've stalled on Obamacare. It's why they're slow on tax reform. It's why infrastructure, which should be a goldmine for lobbyists, is basically on the slow track and may not happen at all.

You know, lobbyists are often paid to stop things from happening, but they're also paid to get things to happen, to put their client's thing, their ask, in some bigger project, some bigger bill. And when the president and his own party in control of Congress can't move these big initiatives, then there's no Christmas for anybody. The bigger wins in lobbying happen when big initiatives move forward in Congress. So in some ways, I think the president's inability to focus on these policies is hurting these guys.

GROSS: He's appointed some people to head agencies who've basically lobbied against them, and one big example about that is the head of the EPA. How does that connect to the larger story of lobbying in Trump's Washington?

CONFESSORE: I think your question goes to the heart of this paradox that people are wrestling with about Trump, which is, is he an ultraconservative of some kind or is he a man without firm moorings on principle, a guy who will deal with Chuck Schumer and Mitch McConnell as easily? And I think the answer is that when you come into office and don't have a long briefing book full of policies or well-developed ideas about what you want to do in office, what you end up with is a lot of opportunists and entrepreneurs taking advantage of the vacuum of ideas in force.

In the West Wing, it's factionalism, but at some agencies, it's the opposite. You know, the president basically hired over a hundred lobbyists to work in his administration, and many of them are working at the agencies they used to lobby. Scott Pruitt, the EPA administrator, is heading an agency he repeatedly sued in his previous life. And again, I think it goes back to the lack of the president's own will here. He basically said, you know what? EPA is yours, guys, take it. The Interior Department - it's yours, take it. And he handed it over to the industries that had the most to gain or lose from regulation in those industries. And he kind of walked away.

GROSS: Let's take a short break, and then we'll talk some more. If you're just joining us, my guest is Nicholas Confessore. He's a political investigative reporter for The New York Times, and he covers wealth, power and influence in Trump's Washington. We'll be right back. This is FRESH AIR.

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GROSS: This is FRESH AIR, and if you're just joining us, my guest is Nicholas Confessore. He's a political investigative reporter for The New York Times and a writer at large for The Times Magazine. He covered campaign finance issues in the 2012 and 2016 presidential campaigns. Now, he covers wealth, power and influence in Trump's Washington, and we're talking about lobbying and whether Trump has actually drained the swamp so to speak.

So you've counted about 20 Trump ex-aides, friends and hangers-on who have made their way into the Washington influence business. So would you - would you do a roll call of some of the people from the Trump campaign as well as Trump friends who have become lobbyists?

CONFESSORE: I can definitely do that. So at the top, the most famous or most infamous, depending on your perspective, is Corey Lewandowski. Corey was the ex-campaign manager. He was fired during the primaries. But in Trump land, you're never really fired. You're always still in the family. And Corey, after the election, was kept out of the White House and so he co-founded a new lobbying firm with another guy who had worked in the Trump campaign. Barry Bennett had also been pushed out of the campaign. You'll see a theme here.

GROSS: (Laughter).

CONFESSORE: A guy you haven't heard so much about is named Robert Stryk, and he's a big part of the story I wrote for The New York Times Magazine recently. And Robert is a good example because he had been a lobbyist but a pretty minor lobbyist in Washington. He didn't really have an office. He lived most of the time in California. He had a couple of clients, like the Vinyl Institute, which is a trade group for vinyl manufacturers. But he happened to be friends with a couple of guys who ended up working on the Trump campaign. And when Trump won, all of a sudden, those relationships were very, very meaningful in Washington. And he got his start by connecting the prime minister of New Zealand, whose deputy ambassador Stryk had met in a bar in Washington, with President-elect Trump over the phone. That was his first gig in Trump's Washington. And he built...

GROSS: Wait, so let's stop right there. He was able to say to the representative from New Zealand who he met at the bar, I can get your president a phone call with President Trump.

CONFESSORE: Exactly. And you're probably thinking, well, can't the president or the prime minister of New Zealand reach the president of the United States? I mean, we're allies.

GROSS: That is what I was thinking (laughter). How

CONFESSORE: How hard could it be?

GROSS: Yes.

CONFESSORE: And the answer is surprisingly hard because in the upset and the chaos after Trump won, nobody knew how to get a hold of him. New Zealand is a great example. They had spent months studying Hillary Clinton's retinue, and they knew who might be in the top jobs, and they had relationships there that they kind of knew who to call.

But when Trump came into office, heads of state all around the world were trying to get in congratulatory pro-forma phone calls, and people didn't know how to get a hold of him. I think I read in one example some prime minister called up a contestant from their country in the Miss Universe pageant to see if she knew how to get hold of Trump. Australia at one point asked the golfer Greg Norman if he knew how to get a hold of President Trump. You had these kinds of weird conversations happening all around the world. And Robert Stryk was able to monetize that. He was able to put that together, and after that, New Zealand hired him for more substantive work for help on some policy initiatives like trade.

Right there you see an example of how the chaos created a new business model. If our own allies can't figure out how to get a phone call into the White House, you can imagine that there is now an entire class of people who can make money making those things happen.

GROSS: So continuing with the roll call, Paul Manafort, who had been forced out as candidate Trump's campaign chair, has lobbied for several foreign interests, including a Ukrainian political party, you know, associated with Russia. But more recently, he's been lobbying for the Kurds, who on Monday voted in a referendum to break away from Iraq. So he's representing the Kurds who want to basically secede from Iraq. But the American government feels that if the Kurds break away from Iraq, that would destabilize the region and be a bad thing.

So in that sense, Paul Manafort is working against the interests of the American government. I should mention, by the way, that as of the time we were recording this, results are not yet in on that referendum. But the Kurds are expected to have voted to break away.

CONFESSORE: That's correct. You know, Paul Manafort was in some ways an originator of this whole lobbying model. The firm he co-founded in the '80s after working on President Reagan's campaign was actually a model. They would work on campaigns for Republicans, and then they would lobby those same Republicans after the campaigns won. And I think Paul Manafort saw the Trump campaign as a way to return to Washington in full force after years of mostly working abroad. That Kurdish work is one example. The work he's under investigation for in the Ukraine and elsewhere in Eastern Europe is a second example.

But his kind of work essentially is he tries to work the levers of the U.S. policy and government apparatus for the benefit of overseas governments and, in some cases, private interests and businesses. So what he's doing in Kurdistan is actually a classic Paul Manafort bid. The irony of course is what he thought was going to be his big return to Washington where he'd run this successful campaign or an unsuccessful one but for the party's nominee and then set himself back up in Washington or at least have access to people in Washington in a big way has really backfired spectacularly. And it could strangle his business, and it could put him in jail.

GROSS: So back to the roll call of some of the people who were in the Trump campaign who either returned to or became lobbyists after the campaign, Newt Gingrich, who was campaigning for President Trump, wrote the book "Understanding Trump." And he's now a senior adviser to a big lobbying firm. So do you see that book "Understanding Trump" as basically being, like, a calling card to potential lobbying clients?

CONFESSORE: It's 100 percent a calling card for lobbying clients, for TV bookers. Look; Newt Gingrich is a smart guy. He's also a Washington fixture. So there is something slightly comic about Newt Gingrich, a guy who has been in Washington for decades, who works for a lobbying firm, who works as a corporate consultant, who makes a lot of money doing this to align himself with the candidate promising to drain the swamp. But as I was saying earlier, the Trump administration is fertile ground for opportunists.

And what we have seen here is Newt Gingrich, you know, kind of positioning himself as a Trump whisperer, as a guy who understands how the president thinks and what is going on in there. I saw Newt Gingrich on the same night that President Trump as a candidate was delivering his speech in Cleveland at the Republican convention. I watched Newt Gingrich brief clients of his lobbying firm (laughter) on the opportunities for them in Trump's Washington. So he's been doing this for quite a while.

GROSS: So returning to the roll call of people from the Trump campaign who became lobbyists, you've got Trump's former political director, Mike Pence's former chief of staff. Have you had the chance to ask any of these people who were campaigning for Trump or, you know, working on the Trump campaign and who were really behind, like, drain the swamp who have subsequently become lobbyists or were already lobbyists and asked them, like, exactly how do you square that - the whole drain the swamp thing - with the fact that you're a lobbyist?

CONFESSORE: Well, I think the answer to that is that over time, the president's definition and his people's definition of the swamp changed. Early on in the campaign, he would talk about lobbyists, but by the end of the campaign and after he became president, the swamp became a new kind of affixation. The swamp was the bureaucracy. The swamp was the Senate. The swamp was the Democrats. The swamp was judges. The swamp was whoever was against what the president wanted to do.

So I think part of the way they have justified this to themselves is to redefine the swamp. The swamp is always somebody else. The swamp is always the other guy. The swamp is the left. The swamp is Mitch McConnell. It's a wonderful term in that you can make it anything you want it to be. And that's what they've done.

GROSS: My guest is Nicholas Confessore, a political investigative reporter for The New York Times. After a break, we'll talk about Steve Bannon and the question, what is Trumpism, and is it now being defined more by Steve Bannon than President Trump? And David Edelstein will review the new film "American Made" starring Tom Cruise. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MARNIX BUSSTRA SONG, "TEN EURO SKUNK")

GROSS: This is FRESH AIR. I'm Terry Gross back with Nicholas Confessore, a political investigative reporter for The New York Times who's also a writer at large for The Times Magazine. He now covers wealth, power and influence in Trump's Washington. He recently wrote about how Trump's presidency changed the rules of influence in Washington and spawned a new breed of lobbyist.

So we've been talking about lobbying in Trump's Washington. I want to ask you about Steve Bannon. He's not a lobbyist, but he has access to a lot of money because he's very close with the Mercer family, which funds a lot of far-right causes and companies, including Breitbart, which Bannon is the head of again. So what are you seeing now watching Bannon's role now that he is no longer in the White House? And to focus that a little bit more (laughter), let's talk about this week's primary election between - in Alabama for the Senate seat that was left vacant when Jeff Sessions became attorney general.

So the president, Trump, supported Luther Strange, whereas Bannon supported Roy Moore, who is very far right - very far right Christian evangelical known for twice having been forced out of his position as head of the state Supreme Court. So what does this say to you that Trump supported one candidate and Bannon supported another?

CONFESSORE: I think the Alabama race is really a case study in the aftershocks of the Trump upset. I think what it fundamentally shows is, Trump unleashed a force in American politics that was always there but was kind of caged within conventional party politics - this nationalism. Sometimes it's white nationalism, but essentially, it's the America First ideology. It's rooted I think partly in economic upheaval and partly in a growing awareness among some white Americans that they are not going to be the top force in American politics and culture forever. And I think once those people who felt that way recognized each other as a movement, it became something that was bigger than Trump. And that's what I think we saw happen in Alabama on Tuesday night.

When you look at it logically, I don't think you can say that Roy Moore is a particularly Breitbart-style candidate or a Trump-style candidate in policy particulars and that Luther Strange, who Moore beat, is somehow some kind of a wishy-washy moderate who's more affiliated with some - you know, with the Washington establishment, a place that he's been in office for only since February.

This was fundamentally a proxy battle of Steve Bannon punishing Mitch McConnell and Bannon trying to wield the influence he has to start a civil war within the Republican Party to displace the people who he disagrees with under the banner of President Trump, but as you can see, not necessarily dependent on what the president himself says or does.

GROSS: You know, I went on the Breitbart site Tuesday night to see what was being written on Breitbart about this victory by Roy Moore. And I'll quote one article. "Trumpism is not about any one person. More importantly, what this humiliating loss tells President Trump is that Trumpism is not even about him. The disputable lesson here for the president is that even he, the man who started the movement, is not bigger than the promises, ideas, agenda and platform he ran on." What does that say to you?

CONFESSORE: You know, not much. I'm not sure the president is himself the best steward of the ideas and platform he ran on. He changes his mind all the time. It's not really about policy, in my mind, or at least the policy is fungible. To me, for the president's base, the president delivers outrage. It's the outrage of the people who dislike the president. And the performance of the presidency, the ability to elicit howls of outrage from people like me in the media, or from Democrats or from others, is the whole point. It is the reward of having him as President Trump. It's not the wall. It's definitely not tax reform. It's the ability to fight that culture war.

That is what President Trump and Roy Moore have in common. That's what they have most in common, is that Roy Moore is the candidate who's going to tick off the supposed powers that be the most, make them the most uncomfortable and the most angry. And I think, fundamentally, that's a piece of why Steve Bannon got behind him. But I think the bigger picture is that Steve Bannon wants to make Mitch McConnell's life difficult.

GROSS: I'm wondering - and I'd be interested in your impression of this - if Steve Bannon perhaps senses that president's - Trump's power is diminishing, that his influence even on his base is diminishing, and therefore, Bannon has to pick up the banner for Trumpism and carry it himself.

CONFESSORE: You know, I think Bannon is the ideologue of the movement, and I use that word neutrally. So his job is to make it mean something beyond any one man. I don't think President Trump makes that easy. It's because he is capricious. It's because he flip-flops. It's because he makes deals with Chuck Schumer and Nancy Pelosi.

So I think Bannon's goal is to build something more enduring and a movement that doesn't depend on one guy whose fortunes are not that great right now. But I think the idea is, first, take over the Republican Party, elect people who you think are in sync with what you're promoting, and then see what you can do in Congress. And now, I'm not sure it's going to work, but I think that's the idea.

GROSS: It's a very ambitious idea.

CONFESSORE: It is. But we saw a version of this with the Tea Party, and the Tea Party remade the Republican Party. There are no - there are almost no old-school moderates in the Republican Party at the national level anymore. They've been obliterated. And the ones that are hanging on, when they retire, will be replaced by either Democrats or much more conservative and aggressive Republicans, in that sense.

GROSS: Where do you see Bannon's politics, compared to the Tea Party?

CONFESSORE: I think that a lot of the Tea Party movement was notionally about government spending. But I think when you look at the social science research on the Tea Party, what you find is a lot of anger and discomfort at the perceived distribution of benefits to people who they thought were unworthy, and that often meant people of color, minorities, African-Americans. I think there are people in the Tea Party who genuinely thought or believe that Obamacare was for black people. And you can see that in social science research. So there's some commonality with the nationalism we're seeing now, which I do believe is partly rooted in this fear of whites no longer being the dominant majority politically and culturally in this country.

But I don't think you can pretend that the Breitbart version of nationalism is closely linked to ideas of government spending. It certainly isn't linked to ideas about tax cuts. I mean, Steve Bannon, to the extent he speaks for this wing - think we should tax rich people more. He's against unfettered free trade. So he's a very, you know, unconventional kind of guy when we talk about conventional party ideology.

GROSS: So his version - Bannon's version of Trumpism isn't the Tea Party.

CONFESSORE: I don't think so. I think it'll probably draw a lot of the same voters. I suspect that a lot of people who identify themselves as Tea Party voters probably are Trump supporters. I'm sure you'd find a high overlap there. The Tea Party started out as a brand for people who were disgusted with Republicans and wanted a different label, so they called themselves the Tea Party. But they were conservatives. And whether the ideological content being supplied by guys like Steve Bannon actually comes to carry the day with voters, we'll see in a couple of years.

GROSS: If you're just joining us, my guest is Nicholas Confessore. He's a political investigative reporter for The New York Times. We're going to take a short break and then talk more. This is FRESH AIR.

(SOUNDBITE OF TED NASH'S "THE FOUR FREEDOMS - FRANKLIN D. ROOSEVELT")

GROSS: This is FRESH AIR, and if you're just joining us, my guest is Nicholas Confessore. He's a political investigative reporter for The New York Times and a writer at large for The New York Times Magazine. He covered campaign finance issues in the 2012 and 2016 presidential campaigns, and now he covers wealth, power and influence in Trump's Washington.

In writing about wealth, power and influence in Trump's Washington, you've written about Mar-a-Lago. How much do members pay at Mar-a-Lago?

CONFESSORE: I believe the current initiation fee is $200,000, which is double what it was before the president ran for president.

GROSS: And what access does that actually give them to President Trump?

CONFESSORE: You know, again, there has never been anything like this in American history where people pay the president to spend time with him. Here's the access they get. The president spends a huge amount of time at his clubs. He has played golf, I believe, on something like a quarter or a third of all his days in office so far, which is by itself an astonishing number.

But Trump is a guy who likes to mix it up and mingle. And so if you were having dinner at Mar-a-Lago, it may be that the president will stop by your table. And if you're someone he knows, he may even ask your opinion about what to do with infrastructure, or how to build the wall or how to handle North Korea. And you may even be witness to the president making decisions with his staff. It's a reality show, only the members are paying for it.

GROSS: You've been trying to find out who the members are. Why is it hard to find that out?

CONFESSORE: Well, it's a private club. We reported on who we think most of the members were as of a few months ago in a story in The New York Times. But it's a private club. They're not required to release their memberships. And right now, there's a fight over whether the president's club has to release logs of who comes and goes when the president is there.

There's a lawsuit at work right now. The president's lawyers said they were going to release it, and then when the deadline came, they essentially gave us a list of some Japanese officials who came to Mar-a-Lago for the meeting with the Japanese prime minister, and they basically didn't release anything else. So it's back in the courts.

GROSS: What do you know about who the members are?

CONFESSORE: So at the time that we did this story, you know, it wasn't clear that a surge of Washington lobbyists had suddenly joined Mar-a-Lago and bought condos in Palm Beach to be close to the president. But there were a lot of people who were already members or who had become members recently. There's a lot of folks in finance and real estate. There was at least one big-time lobbyist in Washington who was a member - you know, people who have major interests before the government and now have a chance to kind of shoot the breeze with the president when he happens to fly down during the season, which is going to be back on us, by the way. I think Mar-a-Lago will be humming again as it grows cooler up here in New York, and the president will be back down there again pretty frequently.

GROSS: You covered money during the Obama era, and you're covering money and influence now during the Trump era. Can you compare what it's been like to cover both of those eras?

CONFESSORE: You know, it's interesting. In the Obama era, certainly, we saw the flourishing of this big-money culture. It began with Republicans. Democrats caught up and tried to match them. And the - you know, a lot of it obviously came out of court decisions like Citizens United, which kind of unleashed big donors in a big way. And, you know, up until 2016, there were just huge amounts of money flowing through American politics in a way that we hadn't seen in a long time.

What's weird and different about the Trump era is it's not clear to me how money is important or where it's important. We saw in Alabama, Mitch McConnell and his allies spent millions of dollars to defeat Roy Moore, and Moore won easily. We saw that President Trump did not have a huge amount of money to spend relative to President Clinton. It did not matter. He eked out a win in the Electoral College.

And if I was going to offer a thesis, I would say that I think we're beginning to see the signs of a real phase shift where elections are driven more and more by social media and digital advertising. People don't trust TV ads on TV very much anymore, and TV ads are very expensive. And we're now entering an era where a lot of political money's going to be spent on Facebook and on social media, and to manipulate you by showing you stuff that you think is coming from your friends and your neighbors, which is a much more powerful tool for changing opinion. I'm not sure how quickly that's going to come, and I'm not ready to say that the era of big money is totally over or dead. But is - it is interesting to me how, in some ways, it seems superfluous.

GROSS: I want to ask you about Puerto Rico, which has - so much of it has just been destroyed by the hurricane. So many people have no water, electricity. Food is running out. Hospitals can't function. So it took Trump about five days to tweet about Puerto Rico. He was sending - spending a lot of time - or at least sending a lot of tweets about, you know, football players taking the knee.

So he finally did tweet about Puerto Rico. And what he wrote was, Texas and Florida are doing great, but Puerto Rico, which was already suffering from broken infrastructure and massive debt, is in deep trouble. Its old electrical grid, which was in terrible shape, was devastated. Much of the island was destroyed with billions of dollars owed to Wall Street and the banks, which sadly must be dealt with. Food, water and medical are top priorities and doing well at FEMA.

You've written in the past about how Puerto Rico became so deep in debt. Why was Trump tweeting about the massive debt - suffering from broken infrastructure and massive debt?

CONFESSORE: You know, it's a great question because it's not clear, like, why he felt the need to talk about the debt at this point in time. You know, one theory is that the president, you know, tends to get one idea stuck on his head on certain topics. And the idea in his head about Puerto Rico is - was the debt. But there is a weird kind of it's-Puerto-Rico's-fault-that-the-hurricane-hit-them tone to those tweets that I think is strange.

What he's talking about is the fact that for many years, through many administrations, the territorial government of Puerto Rico borrowed a lot of money. And its power authorities borrowed a lot of money in bonds. The power authority, in particular, as it borrowed more money and then couldn't meet the obligations on its bonds was essentially stinting on maintenance of its power grid. And that is one reason why the power grid was knocked out so quickly and so completely in this hurricane. The question is, what happens next for Puerto Rico?

What's happened in Washington the last couple of years is that a group of hedge funds essentially has bought up a big chunk, if not most, of that debt, of that bond debt. And they may have bought it for pennies on the dollar. We don't know. And what they've been doing is lobbying in Washington to try to stop the government from allowing Puerto Rico to declare a kind of bankruptcy so that it can wipe out its debt and the bondholders take a haircut and everyone starts over again. They were winning for a while. There was finally a compromise recently in which Puerto Rico was allowed to restructure some of its debt. But the fact is the island owes a lot of money and has no way to repay it. And now it really has no way to repay it because the place has been destroyed.

I don't know why the president decided to bring up the money they owe to Wall Street. The money Puerto Rico owes to Wall Street is never coming back. The island is a catastrophe right now. People are going to start dying in big numbers pretty soon if they can't get water, supplies and food down there. It's going to require a huge amount of government intervention and tax dollars to rebuild our territory in Puerto Rico. And I imagine the president will start focusing on that pretty soon.

GROSS: Well, Nicholas Confessore, I want to thank you so much for talking with us. And thank you for your reporting.

CONFESSORE: It's been a pleasure, Terry. Thank you.

GROSS: Nicholas Confessore is a political investigative reporter for The New York Times and a writer at large for The Times Magazine, where his article "How To Get Rich In Trump's Washington" was published. After we take a short break, David Edelstein will review the new dark comedy "American Made" starring Tom Cruise. This is FRESH AIR.

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