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President Obama And The Courts: A Shift In Balance


This is FRESH AIR. I'm Terry Gross. We're going to talk about President Obama and the courts. There's a lot going on. The president has changed the political makeup of the federal courts, having had 280 judges confirmed. Nine of the 13 federal circuit courts now have Democratic majorities.

But the courts are also being used against the president. One lawsuit, which the Supreme Court has agreed to hear, could gut the president's signature law, the Affordable Care Act. The House of Representatives is suing the Obama administration for overstepping its authority in the way it puts the health care law into effect.

My guest, Jeffrey Toobin, covers the legal system for The New Yorker where he's a staff writer. He interviewed President Obama for a recent New Yorker article about the president's judicial legacy. Toobin is also senior legal analyst for CNN. He's been writing about the Ferguson case and the grand jury decision not to indict Darren Wilson for shooting to death Michael Brown. Toobin's latest book is called "The Oath: The Obama White House And The Supreme Court."

Jeffrey, welcome back to FRESH AIR.


GROSS: So let's start with a recent piece that you wrote for The New Yorker about how President Obama has changed the federal courts - the federal appeals courts. Compare the political makeup now to when he took office.

TOOBIN: It's really a dramatic change. One of the president's - any president's most important duties, though little discussed I think in public, is the opportunity to name judges and justices to the federal courts - to the district court, trial courts, to the courts of appeals and, of course, to the Supreme Court. And, you know, in quick succession, President Obama got two nominees confirmed on the Supreme Court, Sonia Sotomayor and Elena Kagan. But especially in the last two years, Harry Reid, the outgoing Majority Leader of the Senate, really made a special effort to get Obama's nominees through the Senate, and the lower courts have really been transformed over the past two years so that, as you said, 9 of the 13 federal appeals courts are now majority Democratic appointees. And that's especially significant because like the rest of the country and the Congress in particular, the courts are really polarized between Democratic and Republican nominees on lots of high-profile issues. So this matters a lot.

GROSS: So let's talk about how President Obama has been able to appoint so many federal judges when Republicans are blocking his legislation. And this gets back to a filibuster deal that was negotiated during the George W. Bush presidency. Would you describe the deal?

TOOBIN: Well, this, you know, has been a subject of deep disagreement among Democratic and Republican senators. Of course, all judges must be confirmed by a majority of senators. And during George W. Bush's presidency, the Democrats began objecting to a certain number of Bush's appointees, particularly to the important courts of appeals like the D.C. Circuit. And they were engaging in filibusters which meant that 60 senators were necessary to get consideration of any judge, and the Republicans didn't have 60 senators in the end of Bush's term. So what happened was there was a deal negotiated called the gang of 14 senators - agreed that by-and-large there would be no filibusters of Bush's appointees unless there were extraordinary circumstances, a term that was left undefined. But by-and-large it meant that George W. Bush, in his tenure, got the vast majority of his nominees, including some very conservative appointees like Janice Rogers Brown on the D.C. Circuit - Brett Kavanaugh on the D.C. circuit. They were confirmed and now, like all judges, are serving lifetime tenures. And that was basically the status quo when Obama came into office.

GROSS: So Democrats basically agreed to hold their fire except for extraordinary circumstances, and Republicans were supposed to adhere to that, too, should the majority turn Democrat in the next election. And when the majority did turn Democrat in the Senate, did the Republicans hold to that agreement of, you know, not obstructing presidential judicial appointees?

TOOBIN: Well, that was the controversy leading up to the big rules change last year. The Democrats were forced to get 60 votes, not 50, you know, break filibusters, get cloture, in the Senate's term, on nominee after nominee. And with only 55 Democrats then in the Senate, they were having trouble getting their nominees through. So Reid and the Democrats invoked what was called the nuclear option. What that did was it took away the right to filibuster appeals court judges and district court judges. So Democrats only needed a simple majority, not 60 votes, to confirm these lower court judges. That change, which Harry Reid engineered, really allowed President Obama to put his stamp on the courts. He succeeded in getting three new nominees on the D.C. Circuit, which is widely considered to be the second most important court in the country. Several other judges on the First Circuit, on the Fourth Circuit were confirmed.

And that rule of only 51 being required is now still technically on the books. It's sort of a moot point now that there are less than 50 Democrats in the Senate, and obviously one of the big mysteries of the next two years is how many judges the president will be able to get through the now Republican Senate. But, you know, the story of President Obama's success on the judiciary front is really a story about Harry Reid as much as it is about Barack Obama.

GROSS: So when you look at the judges that President Obama has appointed in the past couple of years, what kind of pattern do you see?

TOOBIN: Well, there's a definite pattern. And they are very different in one way, diversity. President Obama has appointed - nearly half of his judges are women. Fewer than half of his judges are white men. Even compared with Bill Clinton, the diversity record is really extraordinary. He's appointed 10 out gay people to be federal judges. It really is a dramatic difference, certainly, from President George W. Bush, but even from Bill Clinton in terms of the diversities of his appointees.

When you look at the ideological profile, however, President Obama has been rather cautious. There have not been a lot or even any sort of fire-breathing liberals appointed. I think Republicans, in recent years, have shown - have been more aggressive and more successful in putting in really very conservative judges. Now, to be sure, most all of Obama's appointees are Democrats, and they tend to look at issues from a more democratic perspective. But he has certainly been cautious from an ideological perspective, though very aggressive in seeking diversity in his nominees.

GROSS: So because of President Obama's judicial appointees, the makeup of the D.C. Circuit Court has changed. You said that's considered, like, the most important of the circuit courts. Why is it so?

TOOBIN: Well, because the jurisdiction of the D.C. Circuit includes challenges to most federal laws. And the most high profile cases about the constitutionality or legality of federal laws wind up in the D.C. circuit. Also, the D.C. circuit has been traditionally a sort of farm team for the United States Supreme Court. There are four justices on the Supreme Court - Chief Justice Roberts, Clarence Thomas, Antonin Scalia and Ruth Ginsburg - who were on the D.C. Circuit before they were on the Supreme Court. So it's important for that reason as well.

GROSS: Well, Jeffrey, why don't we take a break here? And then we'll talk some more about President Obama and the courts. If you're just joining us, my guest is Jeffrey Toobin. He's CNN's senior legal analyst and a staff writer for The New Yorker where he covers legal issues. And his latest book is called "The Oath: The Obama White House And The Supreme Court." We'll be right back. This is FRESH AIR.


GROSS: This is FRESH AIR and if you're just joining us, my guest is Jeffrey Toobin. And we're talking about President Obama and the courts. How he'd transformed the federal courts by appointing many Democratic judges. But at the same time, how he's being challenged in the courts. And Jeffrey Toobin is senior legal analyst for CNN. And he's also a staff writer for the New Yorker where he covers legal issues. To prove the importance of the D.C. Circuit Court, there's a challenge to a part of Obamacare that's been to that court twice. Why don't you describe what that challenge is and if that part of the health care law is knocked down it would kind of gut the Affordable Health Care Act?

TOOBIN: Right. OK. So here's what this case is about - as my father used to say, to make a long story unbearable.

GROSS: (Laughter).

TOOBIN: The Affordable Care Act, as most people know, sets up a system of marketplaces, exchanges where individuals who seek health care can buy it. And - of lesser incomes, there's subsidies available for them from the federal government. Now the law invites each state to set up these exchanges or marketplaces. But many states, particularly the Republican-controlled states, chose not to set up marketplaces. So as the law allows, the federal government set up its own exchanges where in the 34 states without their own state-based exchanges, individuals can buy health insurance and with subsidies, if they need it. One of part of the Obamacare law says the subsidies go to individuals who purchase insurance on exchanges - and here are the four key words - established by the state. A group of conservative lawyers brought a legal challenge which said those four words mean that individuals who buy insurance on the federal exchange in those 34 states, those individuals don't get subsidies.

Now, if this law - challenge is successful it would mean that millions of people - four million, seven million - there is some debate about this, but millions, without question who are getting subsidies now would lose them and presumably, then would lose their insurance. It is an enormously significant lawsuit and as you pointed out, it has been to the D.C. Circuit twice. But then, there was still yet another development that made all of this almost moot.

GROSS: And that's of the Supreme Court agreeing to hear it?

TOOBIN: Correct and everything is on hold, pending the Supreme Court decision in this case which is now called King v. Burwell and which will be argued probably early next year and decided by June.

GROSS: It takes four Supreme Court justices to agree to hear a case. In an instance like this, do you assume if four justices agreed to hear this case that that means that four justices are taking that word state and the Affordable Health Care Act at its most literal meaning and that they would say the federal government can't offer subsidies to insurance holders in the states that don't have their own websites?

TOOBIN: Probably, although we'll never know. One of the oddities of Supreme Court practice is that they never release the votes on agreeing to review the case. We never know how many, whether it's four or five, six. We know it's four or more but we don't know who voted to hear the case. But look, this case obviously brings back memories of the challenge to the constitutionality of the Affordable Care Act which was decided 5-4 in favor of the law in 2012 and it is certainly apparent, or it was apparent, in that case that there are four justices who had a deep distaste for this law and I think it's safe to say for President Obama as well and I think a lot of people - and I would include myself among them - think that it is a very bad sign for the law that the court decided to hear this case.

GROSS: You know, there are several justices who are, like, very literal on their interpretation of the Constitution - Clarence Thomas, Antonin Scalia. In a situation like this when you're talking about a law that was written, you know, like, a couple of years ago, you can ask the people who drafted the law what they meant. It's not the people who wrote the Bible, it's not the people who wrote the Constitution and you're talking about people who are alive and perfectly capable of telling you what their intention was. Does that count?

TOOBIN: Well, that's actually a very controversial question - does it count? Because Justice Scalia in particular is an advocate of what's known as textualism and textualism means that the job of the judge is to evaluate only the words of the statute. Legislative intent, the debates in Congress, what people thought, is entirely irrelevant according to this school of thought. Now, Stephen Breyer, who is Scalia's particular opposite on this point thinks this is very foolish and thinks as respect for Congress requires the Supreme Court to study what the congressional intent was and what makes this controversy so important - I mean, this can all seem very abstract - is in the debates in Congress there was never a single suggestion by any member of Congress that these subsidies were not available to the federal exchanges. Not one person ever suggested that, but, the words of the statute do say, in this one part refer only to exchanges established by the state so this is really a perfect example of textualism versus congressional intent.

Now, supporters of the law would also say it's not just about this one four-word sentence, the entire structure of the law is based on the idea that subsidies are available to individuals from the federal exchanges, but this law suit, this case, will really be a great test of whose philosophy of interpretation is followed.

GROSS: It just seems like there's such a big difference between textual - you know, textualism, when it comes to the distant past - a document from the distant past and a document from yesterday.

TOOBIN: (Laughter). Stephen Breyer agrees with you and it is also true that that historically, the Supreme Court has always looked to congressional intent. That's been very much a part of how the court has interpreted federal statutes for a hundred years, but this area is one where Justice Scalia in particular has made enormous strides in persuading his colleagues that his method is correct.

GROSS: Getting back to that phrase that's being challenged now in the court - established by the state. Is that just like, do we know who actually like, wrote that phrase when it came to like, writing it into the bill? And if they think of it as like, you know, a language oversight, a typo? Like, what's the explanation for why it says established by the state as opposed to established by the government or established by the federal or state government?

TOOBIN: As far as I know, it has not been clearly established who wrote the famous four words, established by the state. It is true that in the old days and not so long ago - the Bush administration, the Clinton administration - Congress would often after passing a major law, pass what was called technical amendments which would clear up ambiguities like this. Congress is so dysfunctional now that they don't do that anymore and they didn't do it in the Affordable Care Act. So the chance to clear this up - which it almost certainly would have been cleared up and made clear that the subsidies go to the federal exchange, as well - didn't happen so this ambiguity was left in, thus, these lawsuits.

GROSS: If the Supreme Court sides with the challengers, what happens to the Affordable Health Care Act?

TOOBIN: Good question. Not clear, except nothing good. If the subsidies are withdrawn from the people who buy the health insurance on the exchanges, it may be simply that they are dropped because they can't afford it. It may be that some scrape together the money to buy the insurance at full price. It is also possible that the Department of Health and Human Services will require health insurance companies to effectively replace the subsidies out of their own pockets, but that could very well throw the insurance companies' calculations way out of whack, forcing them to raise prices so much that the law goes into a sort of death spiral where the prices are so high no one can afford it and the law sort of withers away. All of those are possibilities but I don't think anyone knows for sure precisely what will happen if the plaintiffs win this case.

GROSS: Jeffrey Toobin will be back in the second half of the show. His recent article on President Obama's judicial legacy was published in The New Yorker, where Toobin's a staff writer. He's also CNN's senior legal analyst.

I'm Terry Gross and this is FRESH AIR.


GROSS: This is FRESH AIR. I'm Terry Gross, back with Jeffrey Toobin. We're talking about President Obama and the courts. The president has changed the political makeup of the federal courts, having made 280 judicial appointments. The courts are also being used to challenge the Obama administration. Toobin interviewed the president for a recent article about his judicial legacy, which was published in The New Yorker where Toobin is a staff writer. He's also senior legal analyst for CNN.

So we had been talking about how a part of Obamacare is being challenged, and that's going to be heard by the Supreme Court. At the same time, the House of Representatives is suing the president for extending a requirement of the Affordable Care Act. And why don't you explain what the requirement is?

TOOBIN: OK, the requirement is that - it's very simple - that companies with 50 or more employees have to have health insurance for their employees.

GROSS: And - right. And so Obama has pushed that back - pushed the deadline for that back a couple of times. Now it's 2016, and the House is suing, saying that he doesn't have the authority to do that. At the same time, House Republicans have vehemently opposed everything about Obamacare. So it's a kind of ironic suit. What legal basis does this lawsuit have?

TOOBIN: Well, ironic is one word to describe this lawsuit. Comical is another, though lawsuits are rarely funny. This lawsuit is, I feel safe to say, really going nowhere. It's no wonder that the House Republicans had so much trouble trying to hire a lawyer who would represent them. Just in the big picture, the courts have always said we don't want to get in the middle between fights between the other branches of government. Congress has tools at its disposal to fight with the executive. They can pass laws directing him to behave one way or another and pass them over his veto if necessary. They can impeach the president if they feel he is not following the law. But they cannot pick and choose laws that they choose to file lawsuits about and get the court as the intermediary between the other two branches of government.

This actually came up towards the end of the Vietnam War. There were Democrats in Congress who thought that the war in Cambodia was unlawful, and they sued the Nixon administration to stop the war in Cambodia. And the Supreme Court said no, we are not getting in the middle of this. If you want to pass a law that says the stop the war, help yourself, but we are not going to do that. That's the backdrop to this lawsuit. So I think as a constitutional matter, it is a virtual certainty this lawsuit will get thrown out of court.

However, what makes the lawsuit even more ridiculous, frankly, is, as you point out, the House Republicans - they hate Obamacare. They think all these rules should be delayed until forever. But the part of the law they are choosing to challenge is President Obama moving back a deadline. So the whole thing, frankly, is disingenuous. It's unlikely to have any serious consideration in the courts and is simply a public relations maneuver, which is part of the very real conflict between the House Republicans and now the House majority in the Senate and President Obama.

GROSS: OK. So we've been talking about a suit that the House of Representatives has already filed against Obamacare. The House is also threatening to sue President Obama for overreaching with executive power. Tell us about what that threat is.

TOOBIN: Well, this has arisen in several contexts, but most importantly in response to the president's recent order on immigration. As you know - as everyone knows, this has been a very hot legislative topic throughout the president's tenure. Shortly after the president was reelected, the Senate got 68 votes for a major immigration reform bill. But that - Speaker Boehner never brought that up for a vote in the House of Representatives. And President Obama waited and waited, and he finally, in response to this inaction from Congress, issued an executive order about limiting immigration enforcement against a very substantial number of people, 5 million people. Now, the house Republicans and Senate Republicans have been extremely angry about this. And they say that President Obama has exceeded his authority in removing the threat of deportation from so many million people. And they are threatening a variety of things - a lawsuit, some sort of congressional action - even, perhaps, a censure - all of which are in the air right now. And I think it's unresolved how it will all turn out.

GROSS: So President Obama is said to have spent a lot of time consulting with his legal team and with other legal experts before he issued his executive order about immigration. Based on your knowledge of the law, do you think he has legal grounds for that executive order?

TOOBIN: I do. At its heart, what President Obama's immigration order is about is prosecutorial discretion - is saying we are going to use our immigration authority against this group of people, not that group of people. We are not going to deport the people whose children are American citizens, and that's a lot of people. That seems to me very much within the power of the executive to-do. Now, Congress, if it were so inclined, could pass a law saying you can't do that. But Congress, the House Republicans, the Senate Republicans don't have the votes to do that. So I think this is just an area where the president's authority is clear, and there's not much Congress, in its current form, can do about it.

GROSS: Let's take a look at a different aspect pertaining to the courts facing President Obama, and that is his Attorney General Eric Holder is leaving, and President Obama would like to appoint Loretta Lynch to that position. So let's start with a brief overview of what you think Eric Holder's legacy is.

TOOBIN: Well, I think Eric Holder's legacy looks very different today than it did if he had left at the end of President Obama's first term. I would say that during his first four years as attorney general, he had a very muddled legacy. He failed in his effort to get the Guantanamo detainees tried in federal district courts in the United States. He engaged in a long-term trench warfare with the House Republicans over a variety of semi-scandals and so-called scandals. And he didn't really establish much of a positive record on his own. But in the last two years, he really has changed. And what he has decided is that he wants to be the civil rights attorney general. He filed two very important lawsuits challenging the changes in voting laws in Texas and North Carolina - the restrictions on voting - on early voting, absentee voting, voter IDs. And he has made, both rhetorically and substantively, civil rights the heart of his legacy, including all of his statements and visit to Ferguson where Michael Brown was killed.

GROSS: If you're just joining us, my guest is Jeffrey Toobin. He's CNN's senior legal analyst and a staff writer for The New Yorker where he covers legal issues. Let's take a short break, and then we'll talk more about President Obama and the courts. This is FRESH AIR.


GROSS: This is FRESH AIR. And if you're just joining us, we're talking about President Obama and the courts. My guest is Jeffrey Toobin, who's CNN's senior legal analyst and a staff writer for The New Yorker, where he writes about legal issues. He's also the author of the book, "The Oath: The Obama White House And The Supreme Court."

Let's move on to Ferguson, which you've been, you know, writing about and speaking about on CNN. What are some of the questions you are left with about how the grand jury was handled?

TOOBIN: Well, you know, my view is the best the criminal justice system can hope for is treating everybody the same. And by that, I mean that particularly in a procedural way, that everybody who is suspected of a crime should by and large be treated the same way by the people who are investigating the crime. And I guess my real problem with how the prosecuting attorney, Mr. McCulloch, handled this case is that he set up this really elaborate superstructure of a grand jury investigation. He threw every single piece of evidence in the case into the grand jury and effectively threw up his hands and said to the grand jury, well, do you think there was a crime here? Now, that is not the usual way that prosecutors work. Prosecutors usually use the grand jury as an investigative tool, as a vehicle to get the result they want, usually an indictment, a charge. Or, under Missouri law, they can bring the charge themselves. Now, I don't think that the result in this case was necessarily unjust. The one good thing that Prosecutor McCullough did - and I think it was a good thing - was release all of the testimony and evidence so that all of us can make up our own minds about whether there was an appropriate criminal case to be brought against Officer Darren Wilson. Based on what I have seen, I think a case like that would have been virtually impossible to win in front of a trial jury. Yes, it would've been possible to get probable cause. That's a very low standard. But, you know, my view of the ethical responsibilities of prosecutors is you only bring a case if you think a criminal jury would find this person guilty beyond a reasonable doubt. And I can see why the prosecutor didn't bring this case. I do not think that's necessarily miscarriage of justice. But I think the way he went about it did not contribute to the confidence that we'd all like to see in such a high-profile case.

GROSS: Why do you think the case would have been impossible to win before a jury?

TOOBIN: Because the key issue in this case is the confrontation between Officer Wilson and Michael Brown at the time of the shooting. Now, clearly there was a confrontation between Brown and Wilson at his cruiser - at his police cruiser. But then, they moved about 150 feet away. And that's where the fatal shooting took place. There are several witnesses, including several African-American witnesses, who say that Michael Brown was coming at Officer Wilson. In light of that evidence, I don't think you could get a jury of 12 people to say, beyond a reasonable doubt, that this shooting was unreasonable and a crime. That, to me, is the key evidence.

GROSS: As a legal reporter, have you been going through the documents that McCulloch released?

TOOBIN: I have.

GROSS: What's it like to read them? And how - are you finding it confusing?

TOOBIN: Well, you know, it just shows that - the vagaries, among other things, of eyewitnesses testimony, especially in high-profile cases. There are people who see what they want to see. There are people who see things that are demonstrably untrue. There are people who try, in good faith, to remember what they saw and see very different things from other people who are trying, in good faith, to remember what they saw. There are people with agendas who invent testimony and pretend to see things they clearly didn't see. It gives you, I think, a real sense of humility about the ability of the legal system to reach definite conclusions about events.

GROSS: The prosecutor, Robert McCulloch, told the jurors physical evidence does not change because of public pressure or personal agenda. Physical evidence does not look away as events unfold, nor does it block out or add to memory. He was really emphasizing, like, focus on the physical evidence. Do you think that that was a way of swaying the jury, of saying, like, don't listen to what the eyewitness accounts are; just, like, focus on the physical evidence?

TOOBIN: You know, to tell you the truth, I don't have a real problem with McCulloch saying that. I mean, frankly, it's just true, especially when you have so much contradictory eyewitness testimony. My problem with what McCulloch did relates more to his real abdication of his role as the legal advisor to the grand jury. You know, when I was a prosecutor, you go in there and you say, here's an indictment. And here's the reason why there's probable cause. And this is the summary of the evidence. You don't go in there and say, I don't know. Well, maybe there's an indictment here or maybe there's not, and good luck to you. I mean, that's just not - that, to me, looked like he was placing a thumb on the scale in favor of no indictment. That statement that you read I don't think is a thumb on the scale. But I think other things he did were tacit encouragement of no indictment.

GROSS: So because it was a grand jury investigation and not a jury trial, Darren Wilson was not cross-examined. And so people reading the legal documents - you said everybody can make up their mind for themselves what they think happened. Darren Wilson was never cross-examined. So any holes in his testimony, any challenges to his testimony, were not directly expressed to him. So how does that affect the value of these documents being the final documents on the case?

TOOBIN: Well, I think one of the really shocking and disappointing aspects of the grand jury investigation was the kid-glove treatment of Darren Wilson. One reason why targets of grand jury investigations usually refuse to testify in front of grand juries is that it's only prosecutors in the room. There is no defense counsel. There's no judge. So they can be aggressively questioned. But Darren Wilson was not aggressively questioned. That makes - which is just a tremendous missed opportunity. Now, I don't know if aggressive questioning would have changed the result in this case. But I think it was a very disappointing performance by the prosecutors.

GROSS: Can I just ask you a law 101 question? Why are there grand juries?

TOOBIN: Grand juries were meant as a check on the executive's power to prosecute. If you didn't have grand juries, you would simply let prosecutors decide which people to charge. What the framers thought is, let's establish an intermediate step. Let's make the prosecutor persuade another group of people that the charge is justified. But let's make that an easier step than convicting them. So what you have - in most states and in the federal government, you have the standard of probable cause, which is a lower standard than proof beyond a reasonable doubt. And you also don't have the unanimity requirement. You usually only have to get two-thirds or three-quarters, in most states, of the grand jurors to vote an indictment. So the idea behind grand juries is it's a check, but it's a modest check on executive power.

GROSS: So you said that you don't think a prosecutor could have won prosecuting Darren Wilson before a criminal court in a jury case. But just in terms of the feelings of Americans who are so just kind of emotionally involved in this case, do you think the case would have left Americans with a different feeling had it been prosecuted before a jury with cross examination of Darren Wilson?

TOOBIN: Probably. But, you know, I guess I have to say, this is where the ex-prosecutor in me comes out. You know, I don't think prosecutors should bring cases that they believe they can't win in front of a jury. I just think that's not the right reason to bring a criminal case, to make people happy. I think criminal cases should only be brought if the prosecutor believes there's proof beyond a reasonable doubt. I mean, that's an example of why I think, you know, everybody should be treated under the same rules under the same standards.

GROSS: Well, Jeffrey Toobin, thank you so much. I always enjoy your visits to FRESH AIR. I really appreciate it very much.

TOOBIN: Thanks, Terry.

GROSS: Jeffrey Toobin's recent article on President Obama's judicial legacy was published in The New Yorker, where he's a staff writer. He's also senior legal analyst for CNN. Coming up, our jazz critic, Kevin Whitehead, reviews three jazz books. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.

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