Chief Justice Roberts assigned the opinion to himself. He was still trying to prove that he was cautious and respectful of precedent, as he had claimed to be during his 2005 confirmation hearing. But now he was part of a majority that was, in effect, gutting a four-year-old opinion. Roberts completed this mission with typical finesse, declaring that “the First Amendment requires us to err on the side of protecting political speech rather than suppressing it.” Roberts did not explicitly call for overturning McCain-Feingold, but he left little doubt where the Court was heading. Referring to the McConnell case, the 2003 decision upholding the law, Roberts wrote, “We have no occasion to revisit that determination today.”

“Today.” To those who know the language of the Court, the Chief Justice was all but announcing that five Justices would soon declare the McCain-Feingold law unconstitutional.

Bopp again took an aggressive tack when he began representing David Bossie’s Citizens United group in its effort to broadcast the “Hillary” documentary. The movie had multiple purposes: to advance the conservative cause, to hurt Hillary Clinton’s chances for victory, and to make money. The question, then, was how the F.E.C. would classify the movie and the advertisements for it. Under the F.E.C. rules, if “Hillary” was deemed a work of journalism or entertainment, like “Fahrenheit 9/11,” Bossie could show it anytime he wanted. But if the F.E.C. regarded “Hillary” and commercials for it as an “electioneering communication”—that is, as “speech expressly advocating the election or defeat of a candidate”—then it could not be broadcast during the proscribed election periods.

Bossie went straight to the F.E.C. to get a ruling on “Hillary.” As expected, the F.E.C. ruled that the documentary amounted to an “electioneering communication.” The group then appealed to the federal district court in Washington. A three-judge panel agreed with the F.E.C., holding that the movie “ is susceptible of no other interpretation than to inform the electorate that Senator Clinton is unfit for office, that the United States would be a dangerous place in a President Hillary Clinton world, and that viewers should vote against her.”

Bossie was determined to appeal to the Supreme Court, and at this point he decided to change lawyers. Bossie may have arrived in Washington as a flame-throwing outsider, but during the previous decade he had become part of the conservative establishment. He knew that Bopp had just won the Wisconsin Right to Life case before the Justices, but Bossie’s financial life and potentially his place in history were on the line in Citizens United. He wasn’t going to leave his fate in the hands of a lawyer from Terre Haute.

Instead, he asked Theodore Olson to take the case. Olson was a titanic figure in conservative legal circles. Bossie first met him in the nineties, when Olson and his wife, Barbara, were outspoken fellow-critics of Bill Clinton. (Barbara Olson was killed on the plane that crashed into the Pentagon on September 11, 2001.) As a lawyer at the firm of Gibson, Dunn & Crutcher, Ted Olson had argued and won Bush v. Gore, and was rewarded by President Bush with an appointment as Solicitor General. Olson had argued before the Supreme Court dozens of times, and he had a great deal of credibility with the Justices. He knew how to win.

Olson, a litigator more than an activist, quickly shifted tactics in the case. He tried to narrow the issues in Citizens United, so that the Court would not have to take any dramatic steps in order to rule his way. He did not focus his challenge on the constitutionality of McCain-Feingold; he simply said, as he told the Justices at the oral argument, that the law did not apply to documentaries broadcast with video-on-demand technology, only to commercials. Then Malcolm Stewart, the Deputy Solicitor General, rose to offer his rebuttal, and a single question changed the case, and perhaps American history.

Whenever the federal government is involved in litigation before the Supreme Court, the Office of the Solicitor General handles the representation. In an age when the reputations of many government agencies have suffered, the Solicitor General’s office has remained a symbol of excellence: small, élite, and respected by its most important audience, the Justices.

Since the position of Solicitor General was created, in 1870, some of the most distinguished lawyers in the country’s history have served in it. William Howard Taft, before he became President and then Chief Justice, was an early S.G., and Franklin Roosevelt put two of his Solicitors General, Stanley Reed and Robert H. Jackson, on the Supreme Court. In the sixties and seventies, the office was consecutively occupied by Archibald Cox, Thurgood Marshall, Erwin Griswold (previously the longtime dean of Harvard Law School), and Robert Bork. Kenneth Starr stepped down from a judgeship in the D.C. Circuit to be George H. W. Bush’s S.G.

For all that the Solicitor General serves as the public face of the office, and as an important senior political appointee, the career employees act as its principal representatives to the Court. Only two of the twenty-two lawyers in the office are political appointees, so most move seamlessly from one Administration to the next.

By tradition, the S.G. staff operates according to a different standard from that of the hired guns who generally appear before the Supreme Court. The Solicitor General’s lawyers press their arguments in a way that hews strictly to existing precedent. They don’t hide unfavorable facts from the Justices. They are straight shooters. This is why, in many cases, even when the federal government is not a party, the Court issues what’s known as a C.V.S.G.—a call for the views of the Solicitor General. The lawyers in the S.G.’s office are not neutral, but they are more highly respected than other advocates. They dress differently, too, wearing a morning coat, vest, and striped pants when they appear in the Supreme Court.

Malcolm Stewart, the lawyer in the Solicitor General’s office who argued the Citizens United case, embodied the best of the office. A graduate of Princeton and then Yale Law School, he had clerked for Harry Blackmun in the 1989 term. He joined the Solicitor General’s office in 1993, and his career thrived through three Presidencies and more than forty oral arguments. He twice won a John Marshall Award, one of the highest honors in the department. Shortly before the Citizens United argument, Stewart had been named a Deputy Solicitor General, the highest rank for a career lawyer.

The Justices say that oral arguments rarely make a difference in the outcome of cases. But in Citizens United Stewart’s appearance was an epic disaster.

On the day of Citizens United, Samuel Alito appeared miserable, as usual. Alito enjoyed his job well enough, but he was uncomfortable with its public aspects. He liked reading cases and making decisions. He disliked pomp and bureaucracy. (Alito didn’t even like hiring law clerks. For years, he chose clerks who had worked for him on the Third Circuit, so that he wouldn’t have to interview new ones.) After Thomas, Alito tended to ask the fewest questions of any Justice. But no Justice asked better questions than Alito. It was easy to tell which way Alito was leaning, because his questions were so hard for the lawyer he was targeting to answer. Alito had radar for weak points in a presentation, and in this case he saw a hole in Malcolm Stewart’s.

Alito wanted to push Stewart down a slippery slope. Since McCain-Feingold forbade the broadcast of “electronic communications” shortly before elections, this was a case about movies and television commercials. What else might the law regulate? “Do you think the Constitution required Congress to draw the line where it did, limiting this to broadcast and cable and so forth?” Alito said. Could the law limit a corporation from “providing the same thing in a book? Would the Constitution permit the restriction of all those as well?”

Yes, Stewart said: “Those could have been applied to additional media as well.”

The Justices leaned forward. It was one thing for the government to regulate television commercials. That had been done for years. But a book? Could the government regulate the content of a book?

“That’s pretty incredible,” Alito responded. “You think that if a book was published, a campaign biography that was the functional equivalent of express advocacy, that could be banned?”

“I’m not saying it could be banned,” Stewart replied, trying to recover. “I’m saying that Congress could prohibit the use of corporate treasury funds and could require a corporation to publish it using its—” But clearly Stewart was saying that Citizens United, or any company or nonprofit like it, could not publish a partisan book during a Presidential campaign.

Kennedy interrupted. He was the swing Justice in many areas of the law, but joined the conservatives in all the campaign-spending cases. Sensing vulnerability on the subject of books, he joined Alito’s assault.

“Well, suppose it were an advocacy organization that had a book,” Kennedy said. “Your position is that, under the Constitution, the advertising for this book or the sale for the book itself could be prohibited within the sixty- and thirty-day periods?”

Stewart’s answer was a reluctant, qualified yes.

But neither Alito nor Kennedy had Roberts’s instinct for the jugular. The Chief Justice wanted to make Stewart’s position look as ridiculous as possible. Roberts continued on the subject of the government’s censorship of books, leading Stewart into a trap.

“If it has one name, one use of the candidate’s name, it would be covered, correct?” Roberts asked.

“That’s correct,” Stewart said.

“If it’s a five-hundred-page book, and at the end it says, ‘And so vote for X,’ the government could ban that?” Roberts asked.

“Well, if it says ‘vote for X,’ it would be express advocacy and it would be covered by the preëxisting Federal Election Campaign Act provisions,” Stewart continued, doubling down on his painfully awkward position.

Through artful questioning, Alito, Kennedy, and Roberts had turned a fairly obscure case about campaign-finance reform into a battle over government censorship. The trio made Stewart—and thus the government—take an absurd position: that the government might have the right to criminalize the publication of a five-hundred-page book because of one line at the end. Still, the Justices’ questioning raised important issues. Based on the theory underlying McCain-Feingold, could Congress pass any law to ban a book? And was Stewart right to acknowledge that it did?

Stewart was wrong. Congress could not ban a book. McCain-Feingold was based on the pervasive influence of television advertising on electoral politics, the idea that commercials are somehow unavoidable in contemporary American life. The influence of books operates in a completely different way. Individuals have to make an affirmative choice to acquire and read a book. Congress would have no reason, and no justification, to ban a book under the First Amendment.

As for Stewart’s performance, his defenders pointed to the unique role of the Solicitor General. A private lawyer could have danced around the implications of the law and avoided making any concession, but Stewart had a special obligation to be straight with the Justices, even if the answers hurt his cause. Stewart’s critics—and there were many—said that he had no obligation to try to answer an absurdly far-fetched hypothetical involving the censorship of books. By doing so, according to this view, Stewart wasn’t being honest—he was being foolish. He should have asserted that the federal government had neither the obligation nor the right to stop the publication of a book. Like most arguments about the quality of advocacy, this one had no clear resolution. Evidently, though, the damage to the government’s case had been profound.

At this point, the vagaries of the Supreme Court calendar played a part in the resolution of the case. Citizens United was argued near the end of the term, in late March. (The last arguments are usually at the end of April, and the decisions are released by the end of June.) So there was not a lot of time for the Justices to reach a consensus. At their initial conference, the vote was the same as for Wisconsin Right to Life, with Kennedy joining the four other conservatives.

A private drama followed which in some ways defined the new Chief Justice to his colleagues. Roberts assigned the Citizens United opinion to himself. Even though the oral argument had been dramatic, Olson had presented the case to the Court in a narrow way. According to the briefs in the case—and Olson’s argument—the main issue was whether the McCain-Feingold law applied to a documentary, presented on video on demand, by a nonprofit corporation. The liberals lost that argument: the vote at the conference was that the law did not apply to Citizens United, which was free to advertise and run its documentary as it saw fit. The liberals expected that Roberts’s opinion would say this much and no more.

At first, Roberts did write an opinion roughly along those lines, and Kennedy wrote a concurrence which said the Court should have gone much further. Kennedy’s opinion said the Court should declare McCain-Feingold’s restrictions unconstitutional, overturn an earlier Supreme Court decision from 1990, and gut long-standing prohibitions on corporate giving. But after the Roberts and Kennedy drafts circulated, the conservative Justices began rallying to Kennedy’s more expansive resolution of the case. In light of this, Roberts withdrew his own opinion and let Kennedy write for the majority. Kennedy then turned his concurrence into an opinion for the Court.

The new majority opinion transformed Citizens United into a vehicle for rewriting decades of constitutional law in a case where the lawyer had not even raised those issues. Roberts’s approach to Citizens United conflicted with the position he had taken earlier in the term. At the argument of a death-penalty case known as Cone v. Bell, Roberts had berated at length the defendant’s lawyer, Thomas Goldstein, for his temerity in raising an issue that had not been addressed in the petition. Now Roberts was doing nearly the same thing to upset decades of settled expectations.

As the senior Justice in the minority, John Paul Stevens assigned the main dissent to Souter, who was working on the opinion when he announced his departure, on April 30th. Souter wrote a dissent that aired some of the Court’s dirty laundry. By definition, dissents challenge the legal conclusions of the majority, but Souter accused the Chief Justice of violating the Court’s own procedures to engineer the result he wanted.