How Obama, Roberts Interpret Laws In 'The Oath'

September 17, 2012

Guest: Jeffrey Toobin

TERRY GROSS, HOST: This is FRESH AIR. I'm Terry Gross. My guest, Jeffrey Toobin, has written a new book about the Supreme Court's direction under Chief Justice John Roberts and how Roberts' understanding of the Constitution and the court contrasts with President Obama's. The book is called "The Oath: The Obama White House and the Supreme Court."

Toobin writes that the court has been transformed by the same development that has reconfigured American politics - the evolution of the Republican Party. And this court's rulings, Toobin says, will have greater sway than either the executive or legislative branches over the future of politics, business, public safety, how our elections will be conducted, the place of race in American society and how much power the federal government can exercise.

Jeffrey Toobin is CNN's senior legal analyst and a staff writer for The New Yorker. Jeffrey Toobin, welcome back to FRESH AIR.

JEFFREY TOOBIN: Hi, Terry.

GROSS: So let's start with this. How would you compare President Obama and Chief Justice Roberts' judicial philosophies?

TOOBIN: Well, look, they are obviously very different people. Everybody knows Barack Obama has a very unusual background for a president; born in Hawaii and then led a very peripatetic life. John Roberts had a very stable background. He's from northern Indiana, sort of the outer gravitational pull of Chicago.

But once they entered the meritocracy, they both had similar backgrounds. Both went to Harvard Law School. Both worked on the Harvard Law Review. And both thought a lot about the Constitution. And they have come to dramatically different conclusions that are reflected in every aspect of how the government works today.

GROSS: What are those conclusions?

TOOBIN: Well, one of them believes in change. One of them believes that the Constitution has fundamentally been misinterpreted by the Supreme Court for the past 20 or 30 years, and the one who believes in change is John Roberts, not Barack Obama.

Barack Obama, oddly, and frankly somewhat surprisingly to me, Obama is a great believer in stability, in the absence of change when it comes to the work of the Supreme Court. He is the one trying to hold on to the old - the older decisions, and Roberts is the one who wants to move the court in a dramatically new direction.

GROSS: So I think what you're saying is that Obama is the conservative when it comes to the court, and Robert is the judicial activist?

TOOBIN: That is exactly right, and if you look on issue after issue, whether it's abortion, whether it's civil rights and affirmative action, campaign finance, death penalty, Roberts is pushing the law in a more conservative direction, usually, not always, successfully. And all of those areas, Barack Obama's philosophy is basically better leave it alone, leave it the way it is.

GROSS: Now, when Obama was a senator he voted against the confirmation of Roberts. Do you think that the chief justice holds that against the president now, even though, I mean, he did vote to uphold President Obama's health care reform?

TOOBIN: He did, and of course that's a saga in and of itself, but, you know, John Roberts is a big boy. And John Roberts understands Washington politics. And Roberts understood that Obama was getting ready to run for president when Roberts came up for nomination. The base of the Democratic Party cares about these issues, and he was never going to get Barack Obama - you know, George Bush's nominee for chief justice was never going to get the vote of someone who was considering running for president in the Democratic primaries.

What is surprising and interesting about Obama's reaction to Roberts' nomination was just how much he liked Roberts and how difficult a vote it was for him because Obama is much more conservative when it comes to legal matters than many liberals.

He is not someone who believes in using the courts for social change. He is someone who, as I said, believes in stability, and this was actually a very difficult vote for Obama. He did end up ultimately wind up voting against John Roberts, but it was a much tougher call than you might have thought.

GROSS: Yeah, and you write that some of the legal advisors closest to him said Roberts is the best you're going to get from President Bush as a judicial nominee. So, you know, you should vote for him.

TOOBIN: That's right, and all his - all of Obama's political advisors said: Who are you kidding? You want to run for president, you can't vote for George Bush's nominee for chief justice. So just get it over with and vote against him. But that tension was both real and revealing about Obama's approach to legal issues.

GROSS: Let's look at health care reform and how that was handled in the Supreme Court. Now this law, Obama's health care reform, would have been struck down in the court if Elena Kagan, who was President Obama's first solicitor general, had to recuse herself. Why did she nearly have to recuse herself, and why ultimately didn't she have to?

TOOBIN: Well, Terry, she almost had to recuse herself but for what I think is the most consequential email, perhaps, in American history. Just to refresh people's memory, when the Affordable Care Act, Obamacare, was passed in the Congress, it was early 2010 and Elena Kagan was still the solicitor general. Right around that time, the Obama administration realized that there were going to be legal challenges.

And as, essentially, the chief legal officer in the Justice Department, Kagan was asked to weigh in on those issues, to participate in some meetings about how to defend the law. And her deputy, Neal Katyal, wrote some emails to her and said: Look, this is going to be a big deal. I think you should be involved.

And Kagan wrote back to him: I think you should do it. And that email established that she did not participate in defending the law. Had she participated in defending the law, she would have been recused as a Supreme Court justice, and the decision striking down Obamacare would have been upheld. It's a remarkable behind-the-scenes story of how Elena Kagan, who knew she might be nominated to the Supreme Court, really saved Obama's bacon by thinking ahead in a very savvy way.

GROSS: And speaking of saving, it sounds like she saved that email as evidence.

TOOBIN: Well, you know, all emails are saved, and actually a conservative group who wanted to see Kagan recused in the health care case filed a Freedom of Information Act request, and that's how those emails were produced. They were hoping to find the smoking gun of guilt. They wound up finding the smoking gun of innocence.

GROSS: Now, there were arguments made that Justice Thomas should have recused himself. Why?

TOOBIN: Well, that was a very different scenario, and it related to his wife. Ginni Thomas has been a conservative political activist for decades, since before she met Clarence Thomas. She's worked for the Chamber of Commerce. She worked for then-Congressman Dick Armey. She worked for the Heritage Foundation.

This is a woman who has been politically active for a long time. What was different about her role in the period leading up to the passage of Obamacare is that she started to be very public. She gave a series of speeches. She really crusaded around the country and really denounced Obamacare in a very partisan way.

That led to calls by many people, especially Democratic members of Congress, that her husband Clarence Thomas should be recused. And he, like Kagan, declined to be recused. And in my own opinion, Thomas was right not to recuse himself.

GROSS: Why?

TOOBIN: Because, you know, people's wives and people's husbands have different jobs. And we live in a world where there are lots of two-career families. And people have separate careers. And Ginni Thomas, whether you agree with her or not, this has been her career for a long time. She speaks out on many, many issues. That is not disqualifying in my opinion. Thomas had no financial stake in the Obamacare decision. Ginni Thomas was not going to get a promotion. Her job was not going to be affected by it. She just had political views. And I think the attempt to get him out of the case was really just a transparent attempt to get a likely vote to declare the law unconstitutional off the court. And I think Thomas right to stay in the case, even though I think he was wrong in how he voted.

GROSS: So it was the solicitor general, who - Donald Verrilli, who defended Obamacare in the Supreme Court. He was considered to have stumbled a lot. That led to the assumption that Obamacare was going to be overturned by the court. What were considered his greatest stumbles?

TOOBIN: Well, let me have a moment of candor here and confess that I, when I was working for CNN in sort of my instant analysis role was very critical of Don Verrilli's role. And, you know, my view of Supreme Court arguments is that what the justices say is a lot more important than answer.

Yes, Don Verrilli did not do a great job in answering the questions, but what was so striking about the answers - about the questions - was the degree of hostility he received from Kennedy, from Thomas - not from Thomas. Thomas, of course, didn't ask any questions - from Scalia, from Alito. The passion and the intensity of the hostility to the law was really what was so striking.

And it has been my experience in covering the Supreme Court for quite a while that the justices don't play devil's advocate. They use their questions to try to convince their colleagues of their positions. So it's not - so you can often tell how they're going to vote by how they ask questions.

In this case, let me just say I was completely and utterly wrong about how John Roberts was going to vote in this case.

GROSS: So the solicitor general, Donald Verrilli, seemed to go back and forth about whether the mandate represented a tax or a penalty. Why was so much hinging on which it was?

TOOBIN: Well, this gets into some of the peculiarities of this lawsuit. There is a strange law, which I freely confess I'd never heard of, called the Anti-Injunction Act, which says that taxes can't be litigated - you can't challenge a tax until the tax is actually assessed against you, which makes a certain amount of sense. You know, you can't challenge - you have to sort of be assessed the tax before.

And the Obama administration made the argument at first that, well, since this was a tax, this case was premature. By the time they got to the Supreme Court, they were arguing, well, it's not a tax, it's a penalty. So you can litigate it right away. That was the argument he made in that part of the case. It turned out somewhat to contradict a part of the argument he made in another part of the case.

GROSS: Roberts, Chief Justice Roberts, used the tax premise as the reason why he upheld the law. So just explain that for us.

TOOBIN: Well, this was really the totally stunning denouement of the health care case because all the argument, including the argument in the Supreme Court, had been based on the Obama administration's contention - and this was true in the lower courts, as well - that the law was justified under Congress' power under the Commerce Clause, the provision of Article 1 of the Constitution which says Congress has the right to regulate commerce among the separate states.

And that's really how all - almost all federal laws are justified, that they relate in some way to interstate commerce. That was the heart of the argument. As a subsidiary part of the argument, the Obama administration also claimed that the individual mandate, which is the provision of the law that says everyone has to buy health insurance, either on their own or with a government subsidy, that was also a tax, and Congress obviously has the power to lay taxes, as well.

But that almost never came up in the lower courts or in the Supreme Court, and when the court announced its decision on June 25th, Chief Justice Roberts in his opinion began by saying this law is not justified under the Commerce Clause. The challengers to the law won the main argument in the case.

But then in a really stunning development, and I will never forget sitting there in the Supreme Court hearing the chief justice announce his opinion, he said: But there is a separate justification offered by the administration. And it became clear that he was upholding the entire law, joining with the four liberals on the court in saying that the Affordable Care Act was a tax and thus a permissible use of Congress' power.

GROSS: If you're just joining us, my guest is Jeffrey Toobin, and he is the senior legal analyst for CNN and a staff writer at The New Yorker. His new book is called "The Oath: The Obama White House and the Supreme Court." Let's take a short break here, and then we'll talk some more. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: If you're just joining us, my guest is Jeffrey Toobin. He is a staff writer for The New Yorker, senior legal analyst at CNN and author the new book "The Oath: The Obama White House and the Supreme Court."

So even though he finally upheld the Affordable Care Act, Chief Justice Roberts didn't think that the Commerce Clause justified the act. And the Commerce Clause has become very important for legal interpretations on the right. I'd like you to explain what the Commerce Clause is and why it has become so central.

TOOBIN: Well, it really goes back to the New Deal. Before the New Deal, the federal government really didn't do that much as a national regulator of the economy. But FDR came in, and he passed all this new legislation, and the Supreme Court in the early 1930s struck down a lot of these laws. And the court said, in effect, that Congress has the right to regulate interstate commerce, but that power is narrowly defined.

And these laws, like minimum wage laws, like giving people the right to organize unions, like having Social Security, they were outside Congress' power under the Commerce Clause.

FDR wound up appointing eight justices to the court, and they brought a new understanding of the Commerce Clause, which basically said if Congress thinks any law affects interstate commerce, even at several removes, even if you have to sort of lump a lot of transactions together, we are going to defer to Congress.

And basically what that view of the Commerce Clause did was create the modern welfare state, which says look, we have a big modern country, we need a national regulator of the economy, we need minimum wage laws, we need worker safety laws, and all of that is permissible under the Commerce Clause.

What the conservative movement has done is say, look, that is a misreading of the Commerce Clause, that is an incorrect view, and there is a constitutional justification for cutting back on all sorts of federal regulations and activities, and the Commerce Clause is the way to do it.

GROSS: Since Chief Justice Roberts said he would have overturned Obamacare if he was just examining it through the lens of the Commerce Act, you think in the long run Roberts' interpretation of the Commerce Act is going to be very beneficial to justices on the right in the court.

TOOBIN: I think Chief Justice Roberts' decision will benefit the conservative movement in two different ways. One is the way you suggest, is that their decision on the Commerce Claus in this case is really a shot across the bow to Congress in saying: Look, don't think that the Commerce Clause is a blank check. Don't think you can simply do anything and tell companies and individuals to do anything, and it's justified under the Commerce Clause. That is an important potential marker to Congress to, you know, mind its limits.

But I think it's more beneficial to the conservative movement in a somewhat more indirect way. What John Roberts has done is by supporting Barack Obama on this critical piece of legislation and litigation, Roberts has insulated the court from political challenge for a long time. And Robert has a big conservative agenda still. And he is going to be able to push that agenda without risking criticism now for being a political activist because of this vote.

So look at the issues that are on the horizon for the Supreme Court: the future of affirmative action; the future of the Voting Rights Act; gay rights in many different forms. In all of those...

GROSS: Should we put abortion in there, too?

TOOBIN: Abortion, too. In all of those areas, you know, John Roberts has not suddenly discovered his inner moderate. He remains deeply conservative. He is going to be pushing his agenda, and he now is free from the risk of being accused of politicizing the court because of his vote in this case. And that's a great benefit to the conservative movement.

GROSS: Are you saying you think that's one of the reasons why he voted to uphold Obamacare?

TOOBIN: I do. Again, I'm a little - you know, I'm always a little wary about talking about people's motives, and I can't prove this, but given his conduct in this case, it is very clear to me that Roberts was worried about the institutional place of the Supreme Court in American political life.

He was worried about making this case part of a trilogy, with Bush v. Gore, Citizens United; two highly political cases where five Republican justices did what many people regard as deeply political acts. If he had made the Obamacare case the third in that trilogy, we would be talking about the Supreme Court a great deal more in this campaign. The justices would be political targets in a way that they're not now. And I think that was very much on Roberts' mind.

GROSS: Jeffrey Toobin will be back in the second half of the show. His new book is called "The Oath: The Obama White House and the Supreme Court." He's CNN's senior legal analyst and a staff writer for The New Yorker. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross, back with Jeffrey Toobin. His new book, "The Oath: The Obama White House and the Supreme Court," is about the direction the court is heading in under Chief Justice John Roberts. Toobin is CNN's senior legal analyst and a staff writer for The New Yorker.

Let's take a look back at the Citizens United decision, which is having such a huge effect on this current election and how money is being used. You write that this decision relates to the great themes of the court: corporate power, freedom of speech and the intersection of law and politics.

One of the things that this decision did was basically say that corporations have the right to free speech, like a person does. What precedent did the Supreme Court used in saying - in equating a corporation with an individual when it comes to free speech?

TOOBIN: Well, there is quite a bit of history at the court of viewing corporations with rights, like individuals. I mean, just for example, when The New York Times gets sued for libel, they wave the First Amendment. They say we, you know, we have the right to freedom of speech, freedom of the press. And that is The New York Times as a corporation, and they have that right.

However, the court has always - at least historically - taken a nuanced view of that, which said yes, that is true, but there also can be limits on corporate rights that there are different from human rights. Corporations are not always the same as human beings. Corporations cannot be subject to imprisonment or the death penalty. They do not have rights like equal protection of the laws.

So the court had said for a hundred years that regulating campaign contributions of corporations is one area where corporations are not like people, and that was one of the big changes of Citizens United.

GROSS: Citizens United initially was a very narrow case. And Ted Olson, who is arguing before the Supreme Court representing Citizens United, kept it very narrow. What was he keeping it to?

TOOBIN: Well, you know, Citizens United, what made it so much fun to write about it, is such a bizarre saga in and of itself because the case is this very peculiar set of facts where a conservative group called Citizens United made, frankly, this goofy documentary about Hillary Clinton that was very critical of her during - when she was running for president in 2008.

The FEC - in a frankly bizarre opinion, which I think was wrong - said well, this is just like a political commercial, and you can't run it under the McCain-Feingold law 30 to 60 days - 30 or 60 days before the election. And they - Citizens United challenged it.

Now, Citizens United was not a classic corporation. It was a non-profit. It was a charitable operation. It got most of its money from individuals, not from corporate donors. And Ted Olson, who is a very crafty, practical litigator, said, look. Under the facts of this case, there are lots of ways the Supreme Court could rule in our favor - Citizens United favor - without changing the law in dramatic ways by saying it doesn't apply to - that this law doesn't apply to non-profits, this wasn't really a commercial. And thus, Citizens United would have been forgotten because it was such a minor case if it had gone Olson's Way.

As it turned out, Olson was wrong about how much the court wanted to engage with the big issues, and he wound up winning a much, much bigger victory.

GROSS: Chief Justice Roberts sent Citizens United back to argue a broader case. And you kind of pegged that to the fact that Roberts didn't want Justice Souter to publish the dissenting opinion that he'd written. So I want you to talk about that a little bit. What was Souter's dissenting opinion, and why didn't Roberts want that published?

TOOBIN: Well, this was really an example of an extraordinary, behind-the-scenes struggle at the Supreme Court, because, you know, after the case was argued the first time in this very narrow way, the conservatives on the court really started to get there back up and say, look. We don't want to just declare that Citizens United has the right to run this goofy movie. We want to declare much of the McCain-Feingold law unconstitutional, and we want to establish big, new rules for free speech of corporations and establish more clearly than ever the idea that money is speech.

Souter and the other liberals on the court said, wait a second. This case is a very narrow one, and it was argued in a very narrow way. We think this is simply unfair practice at the Supreme Court to take this narrow case and use it to drive a truck through decades of precedent.

So Roberts came up with a very ingenious solution. Rather than let the Supreme Court have this very ugly public fight about what kind - about how this case was handled by the justices, he said fine. OK. We will reargue the case. We will hear the case argued again, and I will tell the lawyers precisely what's at stake here. I will do what's called the questions presented, which is sort of how the court frames the issues in any given case. They wrote questions presented that showed just how big a case this was. So the case was argued a second time with the higher stakes very clear to all.

So Roberts got to have the big case, but without the criticism from Souter that he had gamed the system.

GROSS: Did the other wing of the court - the liberals or moderates, whatever you care to call them - did the justices have to agree with Roberts' decision to send back the case and to have a broader argument made?

TOOBIN: They didn't. You only need four justices to grant cert in the Supreme Court. They had five who were willing to reargue the case. And, you know, the liberals felt: What the heck? We're losing, anyway. Might as well reargue it, so, you know, maybe lightning will strike. So they didn't exactly oppose the reargument, but they saw the writing on the wall, just like everyone else did.

GROSS: So here's the paradox: If Roberts had the case reargued more broadly because he wanted to prevent this, like, public dissent from Justice Souter, he got the opposite of what he wanted on that account because Justice John Paul Stevens wrote his final dissenting opinion for Citizens United, and it was a scathing opinion, I mean, maybe one of the most scathing dissents ever written.

TOOBIN: It was. It was - I mean, yes, in a way, Roberts didn't get what he wanted in the sense that he didn't get harmony at the court. But by having it argued a second time, he at least could not be accused of sneaking one past the liberals on the court.

By the time the case was argued for the second time, everybody knew the stakes. And Stevens wrote a scathing dissent, but he wrote a scathing dissent on the merits. He didn't say that the justices had played dirty pool. And, frankly, I think the justices are used to disagreeing with each other on the merits, sometimes in very heated waves. I think Roberts knew that was coming, given the stakes in this case, but at the end of the day, it's better to win than to lose.

And sure, Justice Stevens was very critical, but John Roberts and the conservative wing won Citizens United, our politics are transformed, and that's heck of a lot more important than, you know, the complaints of a dissenting and losing justice.

GROSS: I know you have a lot of connections to the court. I'm not sure if the justices spoke to you about this decision directly or not. But do you have any reason to believe that any of the justices who upheld Citizens United are dismayed by the results it's actually having in politics today?

TOOBIN: Quite the opposite. I think Citizens United is the beginning of a major change in American politics, not the end. What you see at the Supreme Court on this issue is a belief that money is speech. That's the core value. And the pioneer of this idea was really Clarence Thomas. Like so many areas of the law, Clarence Thomas has been sort of the leading edge of conservative thought. Whether it's on the Commerce Clause, whether it's on free speech, whether it's on affirmative action or gun control, Thomas has been - you know, began advocating, you know, positions that were out - you know, considered way out there, and they have become the conventional view at the Supreme Court.

Citizens United is only the beginning of the near-complete deregulation that the Supreme Court is going to order. Corporate contributions now can only go to the so-called superPACs. Soon they'll say, well, you corporations can give directly to campaigns. Limit - if you believe that...

GROSS: Why do you think that?

TOOBIN: Well, because the logic follows. I mean, these superPACs are essentially identical to campaign committees. I mean, they are essentially fraudulent contrivances to keep a phony distance between the actual campaign and the separate entities called superPACs. They are part of campaigns, but not legally part of campaigns.

I anticipate that the court, as it's - if it's currently configured - it continues, will say, well, corporations and individuals can give directly to campaigns. And if you believe - as this majority does - that money is speech, how can you have limits on how much you can give to campaigns? Those are, I think, very much endangered. So I think Citizens United is very much the beginning or the middle of deregulations of campaigns, not the end.

GROSS: If you're joining us, my guest is Jeffrey Toobin. He's the author of the new book "The Oath: The Obama White House and the Supreme Court." He's also the senior legal analyst for CNN and a staff writer for The New Yorker.

Let's take a short break here, and then we'll talk some more. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: If you're joining us, my guest is Jeffrey Toobin. We're talking about his new book "The Oath: The Obama White House and the Supreme Court." He's a staff writer for The New Yorker and CNN's senior legal analyst.

You have a chapter in the book that's called "The War Against Precedent." What are the precedents that have been overturned recently by the Supreme Court?

TOOBIN: Well, Citizens United certainly overturned a couple right away: the issue of so-called partial-birth abortion. One of Stephen Breyer's most important opinions was a decision striking down a partial-birth abortion law in - that had been passed in Nebraska.

When President Bush became president, Congress passed essentially an identical law to the Nebraska law, and the Supreme Court upheld essentially an identical law that they had overturned earlier. You see it in the civil rights. We will see it shortly I think in civil rights.

Perhaps the most important opinion of Justice O'Connor's career, 2003, the Grutter opinion, where he - where she upheld the admissions practices at the University of Michigan, a law school, which said that race may be one factor that admissions committees can consider in deciding whether to allow kids to go to school. That is up in this coming term in a case out of Texas, and I have very little doubt that they are going to shrike that down.

You know, it used to be that what it meant to be a conservative on the Supreme Court was, you know, respect for precedent and slow moving change. What's so different about the Roberts court is the way they are burning through many of the precedents they don't like.

GROSS: And you write that the overturning of precedents is being made possible in part through new ways of interpreting the Constitution. So I want to ask you about textualism and originalism. I've heard the word originalism a lot, not so much textualism. What's the difference between the two?

TOOBIN: Well, they're very similar. Originalism is simply interpreting the Constitution as the framers understood it. If you believe that the framers did not establish a - or did not think they were establishing a right of a woman to choose abortion, then there is none in the Constitution. That's the originalist view.

Textualism says we are going to interpret the text of the Constitution narrowly. I mean, one of the great liberal innovations of the 1960s and '70s was the so-called right to privacy, which was established in a series of cases about birth control and abortion and gay rights. And the texturalists say the words right to privacy do not appear in the Constitution, thus we do not recognize one.

Again, it is an attempt to narrow the protections offered to individuals by the Constitution and it's very similar to originalism but it's not identical.

GROSS: OK. In terms of wording, one of the most argued-about parts of the Constitution is the Second Amendment which says: A well regulated militia, being necessary to the security of a free state, the right of the people to keep and bear arms shall not be infringed. So what's the texturalist argument about how to interpret that?

TOOBIN: Well, the texturalist argument is that the two clauses, the so-called militia clause and the right to bear arms clause, are essentially separate. The texturalist view, or certainly the originalist view as expressed by Justice Thomas and Justice Scalia, is that the rights established in the Second Amendment do not belong exclusively to militias; they belong to individuals.

And, again, that is a dramatic change. And even someone like Warren Burger, the Chief Justice before William Rehnquist, thought it was absurd to suggest that the Second Amendment gave individuals a right to keep and bear arms. But Justice Scalia, in the famous Heller Opinion earlier this decade, he established that, in fact, the Second Amendment does establish a individual right to bear arms and he struck down the gun control laws in the District of Columbia.

GROSS: Now, has a grammarian ever been called into the court to argue about the commas and how that affects the meaning of the Second Amendment?

(LAUGHTER)

TOOBIN: Well, you know, you laugh and of course we all laugh but, I mean, that's what texturalism devolves into and Justice Stevens wrote this enormous dissenting opinion in the Heller case where he said, well, I am taking you at your - I'm going to be a texturalist too and I'm going to be an originalist and I'm going to tell you, based on my reading of what was going on in the 1780s, you were wrong about what they thought about the Second Amendment.

So one of the problems with originalism is that it's not always clear what the framers thought about lots of issues. In part, it's not clear because they weren't discussing these issues, and in part because we're dealing with issues that they couldn't have conceived of. What did they think about the regulation of violent video games? You know, I don't think James Madison had a lot of thoughts about violent video games, but if you are an originalist you have to try to extrapolate his views of violent video games.

And that's, some people think, a fool's errand.

GROSS: Do you think that an editor should have sent back the Second Amendment for another revision?

TOOBIN: Definitely.

GROSS: For clarity?

TOOBIN: The Second Amendment is a mess. I mean, these two clauses, you know, you don't have to be a stodgy grammarian to recognize that the sentence simply does not make sense. That the militia clause is tethered to the bear arms clause by a comma but they are otherwise unrelated. And that makes the whole business of texturalism all the more difficult because you have to untangle what they meant, the framers meant, when they did not express themselves clearly at all.

GROSS: If you're just joining us, my guest is Jeffrey Toobin. He's the author of the new book "The Oath, the Obama White House, and the Supreme Court." He's also the senior legal analyst for CNN and a staff writer for the New Yorker. Let's take a short break here and then we'll talk some more. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: If you're just joining us, my guest is Jeffrey Toobin. We're talking about his new book "The Oath, the Obama White House, and the Supreme Court." President Obama has had to appoint two Supreme Court justices so far. You say he hasn't been doing a good job filling judicial appointments in the lower courts. A lot of those benches are vacant. Is that because he hasn't taken the initiative or because his nominations have been blocked?

TOOBIN: Well, this, Terry, is one of the areas that I found the most surprising and it really goes to the central conflict in the book between the conservative Roberts and the so-called liberal Obama. Obama, notwithstanding the fact that he was a Constitutional law teacher at the University of Chicago, one of the great law schools of the country, has shown very little interest in the courts.

It is also true that the Republicans, who are much more engaged on these legal issues, have engaged in a great deal of obstruction of his nominees. But Obama has never even submitted all or even close to all the nominees to fill the vacancies on the court and he has never challenged the Republicans about why they are not confirming his judges.

His absence of interest and engagement on the courts is one of the paradoxes of the Obama presidency, but I think can be explained by his interest in stability and lack of change and frankly not much going on in the courts, as opposed to the Republicans who believe that the courts are one of the great battlegrounds of American politics and government.

GROSS: The opening chapter of your book "The Oath" is about the administering of the oath of office to President Obama by Chief Justice Roberts. And Roberts got a couple words wrong on the oath, so the question was, well, the president didn't take the actual oath word by word as written, so is he still really president? Would anybody try to say that he wasn't?

So the oath was re-given by Chief Justice Roberts. But one of the controversies within that was whether Chief Justice Roberts should say, when he was reading the oath to Barack Obama, so help me God or so help you God. What was that about?

TOOBIN: Well, you know, this is one of the reasons I love being a journalist, Terry, is that, you know, these controversies, these issues, they come and go but, you know, the circus moves on and people move on to other issues. And sometimes you get to go back. And I remember watching the oath, the mal-administered oath on January 20th, 2009 thinking, god, how did they screw it up?

I mean, it's a pretty big deal. And there's a story there, it turns out. And it's the prologue of the oath and the long and short of it is, Roberts prepared meticulously. Some people accused him of, you know, sort of blowing it off. Quite the opposite, is the case. He and his chief assistant, you know, meticulously went over and prepared a card for how the oath would be administered.

Which was emailed to a member of the Congressional committee, a staffer on this committee, but the staffer on the committee never opened the attachment. So the oath card, which is reprinted in my book, never got to the White House. So Obama never saw it. So they were never on the same page about how the words were going to be divided up.

You know, Roberts rehearsed so often that his wife said to him, at this point the dog thinks it's the president.

(LAUGHTER)

TOOBIN: So it was not a lack of preparation, but when Obama sort of jumped in when Roberts didn't expect him, Roberts very uncharacteristically got flustered and the oath, the words got scrambled. And then the question became what legal significance does that have?

GROSS: So I'm going to end with a really silly question.

TOOBIN: Sure.

GROSS: An observation that actually comes from one of our producers. On the cover of your book, "The Oath, the Obama White House, and the Supreme Court," President Obama is in profile on the left side of the cover and Chief Justice Roberts is in profile on the right side of the cover. They're staring at each other the way these images are placed in juxtaposition, and they both have kind of dreamy looks on their face. And it does kind of look like they're about to come together in a kiss.

(LAUGHTER)

TOOBIN: That was the opposite of what I intended.

GROSS: I know.

(LAUGHTER)

GROSS: Has anybody else pointed that out?

TOOBIN: You know, not yet.

GROSS: What do you think?

TOOBIN: But the book's just out. No. The whole point was that they were scowling at each other and, like, in a face off. I think that's a beautiful...

GROSS: Do they look like scowls to you?

TOOBIN: Well, I mean, they look sort of serious. Gosh, I just - now that you mention it, I'm staring at it.

(LAUGHTER)

TOOBIN: You know, maybe this is a clue to how the whole same-sex marriage thing will turn out. That certainly had never occurred to me and the whole point of putting them on the cover was as a face off, but, you know, let love emerge. It would be beautiful.

(LAUGHTER)

GROSS: Jeffrey Toobin, thank you so much. It's always a pleasure to talk with you.

TOOBIN: Great, Terry. Thank you.

GROSS: Jeffrey Toobin is the author of the new book "The Oath, the Obama White House, and the Supreme Court." You can read an excerpt on our website freshair.npr.org where you can also download a Podcast of our show and you can follow us on Twitter @nprfreshair and on Tumblr at nprfreshair.tumblr.com.

Transcripts are created on a rush deadline, and accuracy and availability may vary. This text may not be in its final form and may be updated or revised in the future. Please be aware that the authoritative record of Fresh Air interviews and reviews are the audio recordings of each segment.