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Authors: Jeffrey Toobin

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“We do, Mr. Chief Justice,” Jay said. “That, of course, is not what’s at work here.”

Then Roberts pounced. “Well, I checked the Citizens Clean Elections Commission website this morning,” he said, “and it says that this act was passed to, quote, ‘level the playing field’ when it comes to running for office. Why isn’t that clear evidence that it’s unconstitutional?”

It was a nimble piece of lawyering by the chief justice—a touché moment. But to a layperson, it was an absurdity. The state of Arizona was caught trying to level the playing field—in other words, to do what most people would think was the right thing.

Jay did his best to recover. “Well, Mr. Chief Justice, whatever the Citizens Clean Elections Commission says on its website, I think isn’t dispositive of what the voters of Arizona had in mind when they passed this initiative,” he said. “The Court has recognized since
Buckley v. Valeo
that public financing serves a valid anticorruption purpose, and it does so because it eliminates the influence of private contributions on the candidates who take public financing.” Jay was attempting to speak the chief’s language, albeit in a clearly losing cause.

It was a moment that showed just how much the Court missed Sandra Day O’Connor. It was not just that she was an Arizonan who understood why her state had tried, in this small way, to clean up its politics. But O’Connor had actually run for political office (as no one on the Roberts Court had). She understood the danger of giving individuals and companies unlimited freedom to spend. But Roberts was on a mission—to deregulate American politics. And the chief had the votes.

No one knew this better than Stephen Breyer. He was seventy-two years old at this moment, not old for a Supreme Court justice, but not young, either. The days of his great collaboration with O’Connor were six years in the past. He had built his professional life around the idea that government could be a force for good in America. In particular, he had written a book,
Active Liberty
, that said limits on campaign contributions were the best way to preserve democratic values. And now he saw that the Court was dismantling those limits, sooner rather than later. Breyer gave in to his frustration.

“And what about—it’s a general question. Answer this if you wish. Don’t if you don’t want to, and the same goes for your opponent,” Breyer stammered, near the end of the argument in the Arizona case. “But as
I hear this argument, what’s going through my mind is we are deeply into the details of a very complex bill. McCain-Feingold is hundreds of pages, and we cannot possibly test each provision which is related to the others on such a test of whether it equalizes or incentivizes or some other thing, because the answer is normally we don’t know.” Breyer could see that Roberts and the others were subjecting all campaign finance laws to such exacting scrutiny that none of them could ever survive.

Breyer went on. “And it is better to say it’s all illegal than to subject these things to death by a thousand cuts, because we don’t know what will happen when we start tinkering with one provision rather than another. That thought went through my mind as I’ve heard this discussion. Comment or not upon it as you wish.”

Nervous laughter filled the courtroom. The justices often made speeches in the form of questions, but this was a speech in the form of a speech. No one knew what to say. As the day’s events showed, Kagan was still in there fighting, but Breyer had thrown in the towel.
Just give up on all campaign finance limits. Return American politics to the law of the jungle
.

By the customary vote of 5–4, the Court declared the Arizona law a violation of the First Amendment. The opinions appeared to be a window to the next quarter century at the Supreme Court: Roberts for the majority, Kagan (again assigned by Ginsburg) in the lead dissent. Like
Citizens United
,
Arizona Free Enterprise
showed the conservative agenda for change. Roberts was a modern Republican, not an old-fashioned one (like Harlan, Stewart, Powell, or O’Connor) who believed in judicial restraint. Instead, Roberts was engaging in a consummate act of judicial activism, overruling the will of Arizona’s voters to serve a newly invented legal theory. And, most obviously, the chief justice was doing the bidding of the contemporary Republican Party, which hated campaign finance reform, while Kagan was speaking for the Democrats, who embraced it.

“ ‘Leveling the playing field’ can sound like a good thing,” the chief justice wrote for the majority. “But in a democracy, campaigning for office is not a game. It is a critically important form of speech. The First Amendment embodies our choice as a Nation that, when it comes to such speech, the guiding principle is freedom—the ‘unfettered interchange of ideas’—not whatever the State may view as fair.”

Like the president who appointed her, Kagan sought to limit the power of the Court and to defer to the democratically elected branches
of government. This case, like so many others, revealed how the parties had switched places at the Supreme Court since the 1960s. Then, it had been the Democrats who were the activists, striking down laws that were not to their liking. Now it was the Republicans. “This case arose because Arizonans wanted their government to work on behalf of all the State’s people,” Kagan wrote in her dissent. “On the heels of a political scandal involving the near-routine purchase of legislators’ votes, Arizonans passed a law designed to sever political candidates’ dependence on large contributors. The system discriminated against no ideas and prevented no speech. Indeed, by increasing electoral competition and enabling a wide range of candidates to express their views, the system furthered First Amendment values. Less corruption, more speech. Robust campaigns leading to the election of representatives not beholden to the few, but accountable to the many. The people of Arizona might have expected a decent respect for those objectives. Today, they do not get it.… Truly, democracy is not a game.”

21
“YOU SHOULD DO IT”

B
arack Obama bet his presidency on health care reform. He sacrificed every other legislative priority—including climate change, energy, and immigration—to drag the Affordable Care Act across the finish line. The president’s political adversaries, knowing the stakes, threw everything they had into defeating him. The outcome in Congress was in doubt until the final votes were cast in the House and Senate.

By the time the ACA passed, it was clear that conservatives were going to challenge the bill in court. For two decades, the constitutionality of the individual mandate had never been questioned. But in just a few months, its illegality under the commerce clause became an article of faith within the Republican Party. Opponents of the law lined up to be first to challenge it in federal court. The legal fight over health care reform became a defining symbol of the role reversal that had taken place between liberals and conservatives over the past several decades. Liberals, once the apostles of judicial activism, embraced judicial restraint and deference to the democratically elected branches of government; conservatives, who had railed for so long against judges who, in George W. Bush’s famous phrase, “legislate from the bench,” set out to persuade judges to do just that. Even before the first lawsuit was filed against the ACA, everyone knew the Supreme Court would have the last word. When the case did come before the justices, nothing—no legal argument, no political maneuver, no public appeal—had as much to do with the ultimate fate of the legislation as a single four-word e-mail.

——

Even before Congress voted on the final form of the legislation, lawyers in the Obama administration began organizing a defense. In the typical way of bureaucracies, a group of deputies organized an initial meeting, which senior officials would then decide if they wanted to attend. On January 8, 2010, at 10:54 a.m., an aide to Thomas Perrelli, the associate attorney general, e-mailed Neal Katyal, the deputy solicitor general, about scheduling a meeting for “a group to get thinking about how to defend against inevitable challenges to the health care proposals that are pending.”

Three minutes later, Katyal e-mailed back this enthusiastic reply: “Absolutely right on. Let’s crush them. I’ll speak with Elena and designate someone.”

At the same time, Katyal forwarded the original invitation to Elena Kagan, the solicitor general, asking if she wanted to be included in the group. “I am happy to do this if you are ok with it,” Katyal wrote to her.

Katyal was doing his job, asking his boss if she wanted to attend a strategy session on a major legal issue facing the Justice Department. It was, at one level, a routine communication about who should attend a meeting, and Kagan responded with four unelaborated words. At 11:01 a.m., she wrote Katyal: “You should do it.” The exchange was like thousands that take place in offices every day. (As it turned out, the January meeting never took place. Once Scott Brown, a Republican, won a special election later that month for the Massachusetts Senate seat formerly held by Edward M. Kennedy, it looked like there would be no health care bill at all—so there was no need to figure out how to defend it.)

But the bill came back to life, and in March Obama and the Democrats finally won passage. The denouement came when the House approved a revised measure on Sunday, March 21, by a vote of 219–212. That same day, Perrelli e-mailed invitations to Katyal and others to convene, at long last, the health care litigation planning group. At 6:19 that evening, Katyal forwarded the invitation to Kagan and wrote, “I think you should go, no? I will, but feel like this is litigation of singular importance.” A minute later, Kagan e-mailed Katyal back, asking him for his phone number.

When Kagan and Katyal spoke that evening, she said she had decided to stay away from the health care litigation—which was why,
two months earlier, she had written to him, “You should do it.” Kagan didn’t want to be involved or even informed about work on this issue. Little more was said between them, but the reason for Kagan’s decision was clear. She had been a finalist for the Souter seat the previous year. Stevens was dropping hints that he was going to leave in a matter of weeks. Kagan had a very real chance of being nominated for the Court, and the health care case was likely to come before the justices, sooner rather than later. She wanted to preserve her opportunity to take part. If she became a justice, Kagan did not want to have to recuse herself, so she was not going to participate at all in planning the health care litigation.

Later, when the challenge to the health care law did wind up in the Supreme Court, some liberals argued that Thomas should recuse himself from the case because of his wife’s political activities. In short order, conservatives began asserting in response that Kagan should recuse herself because she must have participated in planning the defense of the law when she was solicitor general. It was a plausible argument. After all, Katyal himself had noted that the case was of “singular importance,” and the solicitor general served, in effect, as the chief legal strategist for the Justice Department. As his e-mails showed, Katyal believed that Kagan should help to defend the law.

In light of all that followed, then, Kagan’s e-mail—“You should do it”—ranks among the most consequential of such messages in American history. It was contemporaneous proof that the future justice had not participated in planning the defense of the law. Katyal’s recollections of their exchanges backed her up. If Kagan had gone to even a single meeting where the legal defense of the health care law was discussed—even if she just sat there and didn’t say a word—she would have been required to recuse herself from participating in the case as a Supreme Court justice. (Justices are not bound by the same formal ethics rules as other federal judges, but attendance at such a meeting would have created a very clear case for recusal.) As would later become clear, the loss of Kagan’s vote would have meant the loss of the case for her side. Without her, at least the individual mandate of the Affordable Care Act would have been invalidated. The e-mail trail kept Kagan in the case.

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