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Jeffrey Toobin writes in the current issue of The New Yorker about Money Unlimited: how Chief Justice John Roberts orchestrated the Citizens United decision. Toobin's article explains how Roberts, by having the case reargued, expanded the scope of Citizens United v. Federal Election Commission from that of a narrow focus of "modest importance" to a wholesale, systemic destruction of our democracy by the hands of moneyed interests. He writes:

Citizens United is a distinctive product of the Roberts Court. The decision followed a lengthy and bitter behind-the-scenes struggle among the Justices that produced both secret unpublished opinions and a rare reargument of a case. The case, too, reflects the aggressive conservative judicial activism of the Roberts Court. It was once liberals who were associated with using the courts to overturn the work of the democratically elected branches of government, but the current Court has matched contempt for Congress with a disdain for many of the Court’s own precedents.
The responsibility for America's post-Citizens United elections were shaped by Roberts and "the credit or the blame goes mostly to him". Toobin explains how the chief justice signaled to conservatives in 2003 that the Supreme Court was actively looking for a case to declare the McCain-Feingold law unconstitutional.

That case came with Citizens United v. Federal Election Commission. Then-Deputy Solictor General Malcolm Stewart argued the FEC's position for the government. His "appearance was an epic disaster"; thanks, in part, to a trap set by the conservatives on the bench. While McCain-Feingold regulated "electronic communications" shortly before an election, Roberts, Samuel Alito, and the other conservatives on the bench wanted to expand the law's interpretation into other mediums.

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.”

Anthony Kennedy latched on to the suggestion opened by Alito's line of questioning.
“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?”
Again, Stewart answered yes. Roberts then went for "the jugular." "The Chief Justice wanted to make Stewart’s position look as ridiculous as possible," Toobin writes. "Roberts continued on the subject of the government’s censorship of books, leading Stewart into a trap."

Stewart 'doubled-down' and awkwardly agreed with Roberts' premise that the government could ban a 500 page book if it advocated for a candidate under the pre-existing Federal Election Campaign Act provisions. Steward got the question wrong, Toobin writes.

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.
The damage was done.
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.
Even though it was obvious after the questioning that Citizens United would win the decision, a battle to expand the scope of the ruling was about to commence. "Roberts assigned the Citizens United opinion to himself," Toobin writes. The losing liberal justices expected the Chief Justice's opinion to be narrow in scope, because the case was presented in "a narrow way".
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.

The majority opinion was about to "upset decades of settled expectations". Earlier in the term, Roberts "had berated at length the defendant’s lawyer" for "raising an issue that had not been addressed in the petition". Now, Roberts was doing "nearly the same thing".
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.

Roberts didn’t mind spirited disagreement on the merits of any case, but Souter’s attack—an extraordinary, bridge-burning farewell to the Court—could damage the Court’s credibility. So the Chief came up with a strategically ingenious maneuver. He would agree to withdraw Kennedy’s draft majority opinion and put Citizens United down for reargument, in the fall. For the second argument, the Court would write new Questions Presented, which frame a case before argument, and there would be no doubt about the stakes of the case. The proposal put the liberals in a box. They could no longer complain about being sandbagged, because the new Questions Presented would be unmistakably clear. But, as Roberts knew, the conservatives would go into the second argument already having five votes for the result they wanted. With no other choice (and no real hope of ever winning the case), the liberals agreed to the rearmament.

On the Court's final day of its term, it was announced to the 'shock' of the litigants and the "political world" that the case was restored for rearmament. "In plain English, the Court’s order told the parties that the Justices were considering overruling two major decisions in modern campaign-finance law," Toobin writes.
As every sophisticated observer of the Court knew, the Court did not ask whether cases should be overruled unless a majority of the Justices were already prepared to do so. And Roberts and his allies were so impatient to overturn these precedents that they were not even going to wait for the first Monday in October. (An early argument would also put a decision in place well before the 2010 elections.)
The second argument of Citzens United expanded the case, but the votes were the same with Sonia Sotamayor replacing Souter in the balloting. Toobin writes:
Because of the much broader Questions Presented, Roberts was now well within his rights to resurrect the earlier draft opinion and lead the charge to bury decades of campaign-finance law.

So, as the Chief Justice chose how broadly to change the law in this area, the real question for him, it seems, was how much he wanted to help the Republican Party. Roberts’s choice was: a lot.

Roberts assigned the winning opinion to Kennedy, which Toobin describes as "another brilliant strategic move". "Kennedy was not a moderate but an extremist—of varied enthusiasms." Kennedy was "extremely receptive to arguments that the government had unduly restricted freedom of speech—especially in the area of campaign finance." He also has a history of dissent, "often in strident terms, anytime his colleagues upheld regulations in that area". Plus, "Kennedy loved writing high-profile opinions." He was the perfect instrument for Roberts to play.
Roberts, during his confirmation hearing, made much of his judicial modesty and his respect for precedent. If the Chief had written Citizens United, he would have been criticized for hypocrisy. But by giving the opinion to Kennedy he obtained a far-reaching result without leaving his own fingerprints.
Despite Stevens "impressive dissent", the longest of his career, the damage was done. With his opinion, Kennedy had confirmed that corporations have the same 1st amendment rights as humans. Kennedy 'reshaped' American politics. Toobin concludes:
The Roberts Court, it appears, will guarantee moneyed interests the freedom to raise and spend any amount, from any source, at any time, in order to win elections.
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