Scoundrel Time

Summary

The Political Scene | The New Yorker

Episode: Scoundrel Time
Date: October 6, 2016
Host: Dorothy Wickenden
Guests: John Cassidy (New Yorker staff writer), Sheila Kolhatkar (New Yorker staff writer)

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Overview

In this episode, Dorothy Wickenden and her guests, John Cassidy and Sheila Kolhatkar, dissect the prevailing voter frustration with business tycoons, big banks, and politicians against the backdrop of the 2016 presidential race. The conversation centers around the explosive revelations of Donald Trump’s nearly $1 billion tax loss in 1995 (exposed by The New York Times) and the Wells Fargo scandal involving fake accounts. The discussion ties these stories to larger questions of accountability, populist anger, the rigged economic system, and the political calculus of both presidential candidates as Election Day nears.

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Key Discussion Points & Insights

1. Trump’s $916 Million Loss and Tax Avoidance

• Background: Trump reported a massive business loss in 1995, allowing him to potentially avoid paying federal income taxes for up to 18 years [01:16].
• Reinvention Post-Bankruptcy: Trump emerged from near financial ruin by selling his brand and via television, rebranding himself as a "success" while not acknowledging past failures.
• "Genius" Spin: Republican surrogates like Rudy Giuliani and Chris Christie publicly called Trump “a genius” for using tax loopholes [01:16].

“Most observers of the tax code have never seen any loss like that for a personal tax filing. A billion dollars.”
— John Cassidy [03:14]

• Bank Bailout: Banks kept Trump afloat with salary and restructuring rather than forcing personal bankruptcy, betting on a better chance of recouping their loans.
• Contractors and Employees: Not paying small businesses and contractors was a pattern for Trump.

“That was his default setting. He always refuses to pay. And everything’s a sort of negotiation then.”
— John Cassidy [05:02]

• Tax Code Loophole: The U.S. tax code allows business losses to offset future income — which is legal but "never been seen... on the scale Trump did" [05:55].

2. Wells Fargo Scandal and Bank Accountability

• Scandal Details: Over 5,300 employees created 2 million fake accounts to hit aggressive sales quotas [06:34].
• Populist Outrage: Senator Elizabeth Warren grilled CEO John Stumpf in a viral Senate hearing, demanding his resignation and criminal investigation:

“If one of your tellers took a handful of $20 bills out of the cash drawer, they’d probably be looking at criminal charges for theft.... you kept your job, you kept your multimillion dollar bonuses, and you went on television to blame thousands of $12 an hour employees... This is about accountability. You should resign.”
— Elizabeth Warren [06:58]

• Easy-to-grasp Outrage: Ordinary workers were pressured and punished, while leadership profited.
• Clawback Explained: Leadership agreed to forgo future stock bonuses (“clawback”), but real accountability remains questionable [09:33].

“It’s sort of like he’s promising to give back something that he had been promised to get in the future. It’s not clear that he’s really giving anything up.”
— Sheila Kolhatkar [09:33]

3. Campaign Responses & Political Fallout

• Clinton’s Wall Street Complications: Hillary Clinton’s Wall Street ties—especially her unreleased Goldman Sachs speech transcripts—complicate her ability to respond forcefully to financial scandals. She has proposed extending Dodd-Frank reforms and curbing high-frequency trading [11:28].
• Trump’s Populist Shift: Although Trump started the campaign talking tough on banks, he’s since softened, possibly due to an increased reliance on fundraising from corporate interests [11:28].
• Scandal’s Impact on Election: Despite public rage, neither candidate is seen as a true “crusader” against the rigged system. The guests agree the Wells Fargo scandal is unlikely to significantly shift votes [13:38].

“I don’t think the Wells Fargo scandal has had that much of an impact on the campaign. I think most people already think that Wall Street is completely crooked.”
— John Cassidy [13:38]

4. Polling and Candidate Weaknesses

• Poll Trends: Since the first presidential debate, there has been a swing towards Clinton, especially in battleground states like North Carolina and Pennsylvania [15:43].
• Elizabeth Warren’s Role: Bringing Warren into a Clinton administration might help address Clinton's Wall Street credibility gap but would terrify many in the financial sector [14:23].

“She literally causes heart palpitations among bank CEOs. I mean, they just think she wants to come in and break their companies up into little tiny community banks.”
— Sheila Kolhatkar [14:23]

5. Populist Sentiments and the “Rigged System”

• Trump as Product of the System: The irony of Trump running as an anti-establishment candidate is discussed, given he benefited from the system he criticizes [16:41].
• Voter Economic Anxiety: Despite controversies, Trump’s simple jobs-focused rhetoric ("Jobs, jobs, jobs") resonates with economically strained voters, even if built on a mythologized self-image [17:34].

“He’s obviously a product of that system. He was born into wealth.... Now we know he’s enriched himself by not paying taxes... So there’s a real irony to that.”
— Sheila Kolhatkar [16:49]

• Electoral Consequences: While core Trump supporters aren't bothered by the tax revelations, persuading swing voters may be harder given the perception of gaming the system [18:23].

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Notable Quotes & Memorable Moments

On Trump’s Losses and Reinvention:
"Trump was then bussed, and slowly but surely, he did dig himself out of the hole... became a reality television star and emerges 20 years later saying, look, I'm the great. A great success. And, of course, it never mentions the fact he lost a billion dollars."
— John Cassidy [03:14]

On Populist Outrage Over Wells Fargo:
“This is about accountability. You should resign. You should give back the money that you took while this scam was going on. And you should be criminally investigated.”
— Elizabeth Warren [06:58]

On Clinton and Wall Street:
"Bringing Elizabeth Warren into her Cabinet somehow would really help address this issue, because Elizabeth Warren is immensely popular with the sort of left side, the critics of Wall Street. At the same time, I think it would cause a heart attack in the financial world."
— Sheila Kolhatkar [14:23]

On Voters and the "Rigged System":
“Trump has been very adept at really speaking to people’s economic insecurity... In a lot of parts of the country, that is what people want to hear. They want a simple message.”
— Sheila Kolhatkar [17:34]

On Electoral Impact of Scandals:
“You have to win over the sort of center ground and the soccer moms in the suburbs, et cetera, people who are not following this closely and may be undecided... it seems to me that the side of a man who has lost a billion dollars and then not paid any federal income tax for... at least 20 years, I just think that is going to damage him with the sort of casual voter, swing voter, et cetera.”
— John Cassidy [18:23]

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Important Timestamps for Segments

• [01:16] – Episode introduction and summary of Trump’s tax loss and the “rigged system”
• [03:14] – John Cassidy explains the scale of Trump’s business losses and recovery
• [05:02] – History of Trump’s pattern with contractors and tax precedent
• [06:34] – Discussion shifts to the Wells Fargo scandal and fraudulent accounts
• [06:58] – Elizabeth Warren’s Senate hearing grilling of Wells Fargo CEO
• [09:33] – Sheila Kolhatkar explains “clawback” and bank accountability
• [11:28] – Clinton’s response to Wall Street issues and campaign implications
• [13:38] – Do scandals affect polls/campaigns? Guest perspectives
• [14:23] – Potential impact of Elizabeth Warren in a Clinton administration
• [15:43] – Poll updates in swing states since the first debate
• [16:41] – The irony of Trump’s anti-establishment positioning
• [17:34] – Trump’s appeal to economic insecurity and jobs
• [18:23] – Electoral consequences of scandals for swing voters

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Summary

The episode paints a portrait of an election season shaped by widespread distrust in economic and political institutions, and candidates who are both seen as emblematic of those broken systems. Through deep dives into the Trump tax story and Wells Fargo scandal, the hosts link elite impunity and populist outrage to broader themes defining 2016—while casting a skeptical eye on whether real change is forthcoming, regardless of who wins.

Transcript

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[Dorothy Wickenden]

This is the Political Scene, a weekly conversation with New Yorker writers and editors about Politics. It's Thursday, October 6th. I'm Dorothy Wickenden, executive editor of the New Yorker. Donald Trump likes to talk about the rigged system. It's one thing he's right about when he applies the term to tax avoidance by the super rich. On Saturday, the New York Times reported that in 1995, Trump claimed a loss of almost a billion dollars, which could have entitled him to legally avoid paying federal income taxes for almost two decades. On the Sunday talk shows, two of his most prominent Republican Party surrogates, former Mayor Rudy Giuliani of New York and Governor Chris Christie spinning desperately, declared him a genius. On Monday, Hillary Clinton spoke to supporters in Toledo. The whole story tells us everything we need to know about how Trump does business. After he made all those bad bets and lost all that money, he didn't lift a finger to help and protect his employees or all the small businesses and contractors he'd hide, hired or the people of Atlantic City. They all got hammered while he was busy with his accountants trying to Figure out how he could keep living like a billionaire. The banking system, like the tax code, is also rigged. As the Trump story unfolded, there were developments in another scandal. It involves years of malfeasance by Wells Fargo Bank. John Cassidy and Sheila Kolhatkar join me today to discuss voters rage at business tycoons, big banks and politicians, and how the two candidates are handling it as they approach Election Day. Thank you both for being here.

[John Cassidy]

Thanks, Dorothy.

[Sheila Kolhatkar]

Thank you. Great to be here, John.

[Dorothy Wickenden]

Let's start with Trump's astounding $916 million loss in 1995. He sold himself to the voters as a phenomenally successful businessman. How did he lose all that money and then rebound from several bankruptcies?

[John Cassidy]

Well, he's certainly a phenomenal businessman. I mean, most observers of the tax code have never seen any loss like that for a personal tax filing. A billion dollars. So you've got to give how did it happen to him? How did he come back? Donald TRUMP, in the 80s, if you remember back, was part of the sort of great leveraged boom of the time. Borrowing money from everywhere, junk bonds from banks to buy up businesses, buying buildings. He bought an airline, he bought the Plaza Hotel, he bought and built casinos in Atlantic City. Did virtually all of that on borrowed money. At the end of the 1980s, start in the 1990s, there was a big real estate recession. As you remember, a lot of his businesses just lost a fortune. We now know a billion dollars at least. Most people would have been declared bankrupt and that would have been the end of it. What happened with Trump is a couple of his individual businesses did get put into bankruptcy and he sold off his airline, the former Eastern Shuttle and the Trump Shuttle. And the banks, it seems rather than declaring him bankrupt, he owed them a fortune. They decided to keep him afloat and do a sort of restructuring process where they put him on a minimal salary. And he basically was just trying to pay down the debt and survive. The banks basically dec that they had a better chance of getting their money back by keeping him afloat and not putting him into personal bankruptcy than by declaring him bust. To all intents and purposes, Trump was then bussed, and slowly but surely, he did dig himself out of the hole. There was a big restructuring done in the mid-90s. It was a private thing, so we don't have all the details on it, but some of his debt was certainly forgiven. He sold off a lot of things and he then reinvented himself as more a franchiser than developers, Selling his name to all sorts of things became a reality television star and emerges 20 years later saying, look, I'm the great. A great success. And, of course, it never mentions the fact he lost a billion dollars.

[Dorothy Wickenden]

And what about the stiffing of contractors and employees?

[John Cassidy]

That has been a constant of Trump's career. And both before, after he went bankrupt. I mean, I remember one of the stories I read about him was a guy who deals with him in Atlantic City, and he said, of course, Trump didn't pay. That was his default setting. He always refuses to pay. And everything's a sort of negotiation then. And, of course, he's stiffed the taxpayers by rolling over this enormous loss. So we think $900 million, and he seems to have been rolling that over for years. The tax code, one of the quirks of it is that you can use the losses from previous years, if you're a businessman, to offset against income in future years. In a lot of cases, that's a legitimate thing to do. Restaurants, for example, might lose the first year when they open up because they don't do all the building and marketing, and then they make money the second year so they can offset the losses in the first year against the second year. Lots of small businesses do that. That is legitimate. What's never been seen before, as far as I know, anyway. Is anybody doing it on the scale Trump did?

[Dorothy Wickenden]

He says it gives him special knowledge of the tax cod, which he then would change, but presumably he would not change these particular loopholes.

[John Cassidy]

Yeah, well, he has got a tax reform, but it looks like actually his tax reform would end up benefiting people like him. One of his main changes is to reduce the top rate of tax from 40% down to 15% on business income. And it's a bit complicated, but businesses like Trump, they do something pass through. They don't get taxed as corporations. They get taxed as private individuals because all their money is in limited partnerships, et cetera. And Trump's tax plan would give a big tax cut to people who do that, including him.

[Dorothy Wickenden]

The Wells Fargo revelations are also off the charts in terms of greedy audacity. We now know that at least 5,300 employees over the years created some 2 million fake accounts in order to meet sales targets. Senator Elizabeth Warren, who channels leftist populism, grilled the CEO John Stumpf, a few weeks ago during a Banking Committee hearing.

[Elizabeth Warren]

If one of your tellers took a handful of $20 bills out of the cash drawer, they'd probably be looking at criminal charges for theft. They could end up in prison. But you squeezed your employees to the breaking Point so they would cheat customers and you could drive up the value of your stock and put hundreds of millions of dollars in your own pocket. And when it all blew up, you kept your job, you kept your multimillion dollar bonuses, and you went on television to blame thousands of $12 an hour employees who were just trying to meet cross sell quotas that made you rich. This is about accountability. You should resign. You should give back the money that you took while this scam was going on. And you should be criminally investigated by both the Department of Justice and the securities and exchan.

[Dorothy Wickenden]

Sheila, help us get a handle on this. Banks are fined after engaging in this kind of wrongdoing. And since the financial crisis there have been significant financial reforms. Yet Stump's stock holdings increased, increased in value by $200 million over the course of the scam. How can this happen?

[Sheila Kolhatkar]

Well, I think one of the reasons this has resonated so much and so powerfully with people and including people in Washington like Elizabeth Warren, is because it's really easy to understand. So you had these sort of low hourly employees worried about losing their jobs. A number of them have filed lawsuits since this all came out saying they were fired for not meeting these really aggressive quotas they had. So there they were, incentivized, fearful perhaps that if they didn't open eight accounts per customer, they were gonna lose their jobs, which just seems absurd on the face of it. Then on the other end of the scale, you had the top leadership of the company, like the CEO Stumpf, accumulating over a handful of years, 200, $100 million in compensation, including unvested stock. And it's just sort of a stunning contrast. And it is so easy to look at those two ends of the spectrum of Wells Fargo and just feel like there's something profoundly wrong there. And I think it's the same kind of rage that has driven a lot of this very unusual political season that we've seen.

[Dorothy Wickenden]

Absolutely. Is there going to be a criminal investigation? Warren is calling for one. And will Stumpf have to resign? I know there's been this clawback and maybe you can expl what a clawback is. Exactly.

[Sheila Kolhatkar]

Well, so a clawback is a great term. I mean, it basically means if you do something that endangers the company, causes a huge loss, you may be asked or required to give back some of the money that you made. And this has been a recurring problem on Wall street where you had traders, investment bankers, incentivized by this generous bonus system to take huge risks, roll the dice See if they could make a huge sort of payoff in one or two years, they get a bonus off of that and then six, the trade can go south and suddenly this thing that made you a lot of money last year or last month is losing a lot of money. Your bank might even need a government rescue of some kind. So how is it people asked that that person can keep all that money they made doing this sort of risky short term thing? So they institute. A lot of banks adopted this idea of clawbacks. This was part of some of the reforms that were passed after the financial crisis. Stumpf, it appears in an attempt to retain his job, has agreed at the behest of the board of the company to claw back some of his Pay. So about $41 million in unvested stock. However, news reports about his compensation have suggested that he hadn't actually even received all that stock. So although it's called a clawback, it's sort of like he's promising to give back something that he had been promised to get in the future. It's not clear that he's really giving anything up. I don't know if it's going to satisfy people. And Elizabeth Warren, among others, have called for criminal investigation of the bank. The high level executives and a lot of people are asking questions, why were only the low level people fired for this?

[Dorothy Wickenden]

John, how does Hillary Clinton deal with this? She, of course, is vulnerable. The second presidential debate is coming up on Sunday. Certainly Trump will come up with some question about her ties to Wall Street. How does she do on this question and what has she said about the Wells Fargo scandal?

[John Cassidy]

She hasn't said much about the Wells Fargo scandal, I don't think. I mean, the whole Wall street issue is a bit tricky for Hillary, obviously, because of her speeches to Goldman Sachs, which she's still refusing to release the transcripts of. I'm sure if Trump does bring it up, her reply will be, look, I've got a whole set of proposals to crack down on Wall Street. Trump's got nothing. She basically has got a series of proposals out there to extend the reforms, to extend Dodd Frank crack down on high frequency trading. She has made proposals for how the big bank so that there's no chance of them going bust again and putting the taxpayer on the hook again. There's some debate about whether those provisions would actually work very well, but I think it's fair to say that Hillary has got a much more comprehensive and complete Wall street package than Trump has. Trump talks about bankers, or he used to talk about the murdering, the campaign, about bankers getting away with everything. But recently he's gone soft on that. Maybe it's because he's now raising money from a lot of big corporate and Wall street interests. It will be interesting to see whether he does go back to that populist language in the debate.

[Katie Drummond]

I'm Katie Drummond. I'm Wired's global editorial director. I'm Michael Colory, Wired's director of consumer, tech and culture.

[Dorothy Wickenden]

And I'm Lauren Good.

[Sheila Kolhatkar]

I'm a senior correspondent at Wired. And our show, Uncanny Valley, is all about the people, power and influence of Silicon Valley.

[Katie Drummond]

At Wired, we're constantly reporting on how technology is changing every aspect of our lives. So each week on the show, we get together to talk about one of the biggest stories in tech. Right? So whether we're talking about privacy, AI, social media, or a major tech figure, we will always explain the Silicon Valley forces behind these stories and how they affect you. Make sure you're following Uncanny Valley in your podcast app of choice so you don't miss an episode.

[Dorothy Wickenden]

Here we have these two very flawed candidates who are widely unpopular. What are you seeing in the polls right now as these stories unfold? Are voters paying attention to these kinds of scandals?

[John Cassidy]

I don't think the Wells Fargo scandal has had that much of an impact on the campaign. I think most people already think that Wall street is completely crooked, and they just say, hey, here's another example of the bank screwing people. I don't think either of the candidates we've got left in the race, it sort of plays naturally into their strengths. Trump, as I say you would think, might have been able to tap into it more. But I've certainly noticed in the last few months his sort of populist rhetoric on this, on bank has really been toned down. And Hillary, she always says, you know, she's going to crack down on the banks. But lurking in the background, of course, is this sort of Goldman Sachs issue.

[Dorothy Wickenden]

And Sheila, what do you think about Elizabeth Warren and the possibility that Hillary might want to give her some Cabinet post or some other position in the administration?

[Sheila Kolhatkar]

And I think that would clearly help offset a major weakness that people see in Hillary Clinton. And this is something that Bernie Sanders incredible success really exposed, which is, yes, she's weak on this point. People don't really trust her to regulate and be tough on Wall street, even though on paper what she has sounds pretty reasonable. Bringing Elizabeth Warren into her Cabinet somehow would really help address this issue, because Elizabeth Warren is immensely popular with the sort of left side, the critics of Wall Street. At the same time, I think it would cause a heart attack in the financial world if Elizabeth Warren took on some prominent post in the Clinton administration because they really strongly dislike her. This is something I've reported on in the past. I mean, she literally causes heart palpitations among bank CEOs. I mean, they just think she wants to come in and break their companies up into little tiny community banks.

[John Cassidy]

What job could they give her? Sheila, Are we talking head of the sec, Treasury Secretary? What's the cftc?

[Sheila Kolhatkar]

I don't know. It's a good question. I mean, she couldn't even get confirmed to run the Consumer Financial Protection Bureau, which was her creation.

[Dorothy Wickenden]

So, although that was a little bit earlier and we're now at a different.

[John Cassidy]

Political point, Democrats might take over the Senate. So she'd be in good shape then.

[Sheila Kolhatkar]

I think a lot of it depends.

[John Cassidy]

On the latest polls, you know.

[Dorothy Wickenden]

Well, talk about the latest polls since the first presidential debate.

[John Cassidy]

Yeah, I mean, we basically had a significant swing to Hillary in the last couple of weeks. Obviously, you don't want to take any one poll too seriously, but the polls of polls now show are up by four or five points. And in a lot of the swing states, there's been a swing to or 2. For example, in North Carolina, there was a poll that came out a day or two ago. Trump really has to win North Carolina. It should be in the Republican column if Republicans are going to win the White House. And Hillary appears to be ahead in North Carolina. In Florida, Trump had moved into the lead. Now the polls look very close again. Pennsylvania, which is a critical state if Trump was by any chance going to win, he really needs to win Pennsylvania. Before the last debate, it looked like he'd closed the polls to maybe four or five points. Now it seems to be back to seven. Things have looked a lot better in the last week or two for Hillary, and now stories are starting to emerge. Are the Republicans in Congress and senators going to try and distance themselves from Trump to save their own necks if he has another bad debate? I think that might well happen.

[Sheila Kolhatkar]

I was just going to mention there's obviously a certain rich irony in the idea of Trump running as the candidate who's against the rigged financial system.

[Dorothy Wickenden]

Exactly.

[Sheila Kolhatkar]

He's obviously a product of that system. He was born into wealth. He was given $14 million, a paltry sum in his characterization from his father. To start his business, he made some irresponsible decisions, reckless decisions, borrowed money he probably shouldn't have borrowed, expanded too fast, collapsed, was bailed out. You know, he had sort of a rescue available to him that most business owners would not. And now we know he's enriched himself by not paying taxes, by exploiting the tax code, and by obviously not paying many of his employees. So there's a real irony to that.

[Dorothy Wickenden]

I agree with you. Although there are many who don't. The billion dollar figure, do you think that that is contributing to what has become more in the past week, declining popularity?

[Sheila Kolhatkar]

I think his attempt to spin that as a brilliant move is going to be difficult.

[Dorothy Wickenden]

Genius.

[Sheila Kolhatkar]

Genius move, yes. I think that's gonna be tough. But I have felt all along that he has been very adept at really speaking to people's economic insecurity. And, I mean, I printed out this economic speech he gave in Nevada, I think, yesterday, and he had some really good lines in here. You know, he said, my economic agenda is very simple, Jobs, jobs, jobs. And I think in a lot of parts of the country, that is what people want to hear. They want a simple message, because there are many parts of the United States where there is no hope for industry returning. Right. And people are in trouble. And I think Trump has been very good at tapping into that, even if it is built on a sort of false narrative about himself.

[John Cassidy]

I agree with that. I mean, I think the issue with Trump and the whole taxes thing, basically two sets of supporters. I think the core Trump supporters, it doesn't do him any harm. He can say, look, I'm a genius. They say he is a genius. Look how he used the tax system. He didn't pay any tax. I wish I didn't have to pay any tax, but in order to actually win the election. I know analysts keep saying this, but it's actually true. You have to win over the sort of center ground and the soccer moms in the suburbs, et cetera, people who are not following this closely and may be undecided and not really interested in politics. It seems to me that the side of a man who has lost a billion dollars and then not paid any federal income tax for what looks like to be at least 20 years, I just think that is going to damage him with the sort of casual voter, swing voter, et cetera.

[Dorothy Wickenden]

Thank you. Both John Cassidy and Sheila Kolhatkar are staff writers. John is the author, most recently of How Markets the Logic of Economic Calamities. Sheila is working on a book about the government crackdown on insider trading on Wall Street. This has been the Political Scene from the New Yorker. You can find more political analysis and commentary on new yorker.com or on the New Yorker apps available at no extra charge from the App Store and Google Play. And you can subscribe to this and other New Yorker podcasts by searching for for the New Yorker in your podcast app. The Political Scene is produced by Alex Barron and Jill Duboff. For newyorker.com I'm Dorothy Wickenden.

[Katie Drummond]

I'm Katie Drummond. I'm Wired's global editorial director. I'm Michael Colory, Wired's director of consumer, Tech and Culture.

[Sheila Kolhatkar]

And I'm Lauren Good. I'm a senior correspondent at Wired. And our show Uncanny Valley is about the people, power and influence of Silicon Valley.

[Katie Drummond]

And right now, Silicon Valley and Washington have never been more intertwined. So each week we get together to talk about a big story, often at the intersection of tech and politics. Right? So whether we're talking about Trump, Coin Doge, or Elon Musk, we will always explain how these Silicon Valley forces are affecting Washington and how they affect you. Make sure you're following Uncanny Valley in your podcast app of choice so you don't miss an episode.

[Sheila Kolhatkar]

From PRX.