How Amy Coney Barrett broke away from Chief Justice Roberts on Trump immunity ruling

(CNN) — The hardline approach Supreme Court Justice Samuel Alito takes usually gets him what he wants.

This year it backfired.

Behind the scenes, the conservative justice sought to put a thumb on the scale for states trying to restrict how social media companies filter content. His tactics could have led to a major change in how platforms operate.

CNN has learned, however, that Alito went too far for two justices – Amy Coney Barrett and Ketanji Brown Jackson – who abandoned the precarious 5-4 majority and left Alito on the losing side.

As a result, the final 6-3 ruling led by Justice Elena Kagan backed the First Amendment rights of social media companies

It is rare that a justice tapped to write the majority opinion loses it in ensuing weeks, but sources tell CNN that it happened twice this year to Alito. He also lost the majority as he was writing the decision in the case of a Texas councilwoman who said she was arrested in retaliation for criticizing the city manager.

Alito has long given off an air of vexation, even as he is regularly in the majority with his conservative ideology. But the frustration of the 74-year-old justice has grown increasingly palpable in the courtroom. He has seldom faced this level of internal opposition.

Overall, Alito wrote the fewest leading opinions for the court this term, only four, while other justices close to his 18-year seniority had been assigned (and kept majorities for) seven opinions each.

His unique year in chambers was matched by the extraordinary public scrutiny for his off-bench activities, including lingering ethics controversies and a newly reported episode regarding an upside-down flag that had flown at this home in January 2021, after the pro-Donald Trump attack on the US Capitol. Some of the rioters waved inverted flags that became a symbol of Trump’s protest of the election results giving Joe Biden the presidency.

After The New York Times reported on the flag in May, Democratic members of Congress called for Alito to recuse himself in Trump-related cases. Alito declined, in a letter that explained that his wife had hung the inverted flag in response to a nasty confrontation with a neighbor.

Alito declined CNN requests for an interview.

This exclusive series on the Supreme Court is based on CNN sources inside and outside the court with knowledge of the deliberations.

Split rulings from Trump-nominated judges divided SCOTUS

The Texas and Florida disputes grew from conservative claims that their viewpoints were being censored online by Facebook, Twitter (now known as X) and other platforms.

The states enacted their laws in 2021 and, with variations, restricted the ability of social media platforms to filter third-party messages, videos and other content. The laws were passed a few months after Facebook and Twitter removed Trump from their platforms, in the wake of the Capitol attack.

When Texas Gov. Greg Abbott signed that state’s measure, he said, “there is a dangerous movement by social media companies to silence conservative viewpoints and ideas.” In Florida, Gov. Ron DeSantis declared in a statement, “If Big Tech censors enforce rules inconsistently, to discriminate in favor of the dominant Silicon Valley ideology, they will now be held accountable.”

NetChoice, an internet trade association, brought lawsuits in both states, saying the laws broadly violated the First Amendment rights of social media companies. US district court judges in Florida and Texas temporarily blocked the laws from taking effect.

As Texas appealed, the 5th US Circuit Court of Appeals, known for its own right-wing streak, said the platforms’ content-moderation activities did not rise to “speech” that would be protected by the First Amendment.

US appellate Judge Andrew Oldham, a former Alito clerk, belittled the “large, well-heeled corporations that have hired an armada of attorneys from some of the best law firms in the world to protect their censorship rights.”

The 11th US Circuit Court of Appeals, however, ruling on the Florida law, took the opposite tack and declared that content moderation implicated the First Amendment and protections for “editorial discretion.” Writing that decision, US appellate Judge Kevin Newsom said, “‘content-moderation’ decisions constitute protected exercises of editorial judgment.”

(Newsom and Oldham were both appointed by Trump, who also has often complained of online censorship.)

When the Supreme Court heard oral arguments in the paired appeals on February 26, the justices struggled with multiple threshold issues, including how the laws might apply to typical social media platforms such as Facebook and YouTube, as well as to sites and apps like Etsy and Uber. NetChoice had brought a broadscale challenge, arguing that the laws were unconstitutional in all situations, rather than pointing to specific cases where free-speech rights were violated.

A few days later, as the justices met in private on the dispute, they all agreed that NetChoice’s sweeping claims of unconstitutionality had fallen short and that the two cases should be sent back to the lower courts for further hearings.

The justices, however, split over which lower court largely had the better approach to the First Amendment and what guidance should be offered for lower courts’ further proceedings.

Alito, while receptive to the 5th Circuit’s opinion minimizing the companies’ speech interests, emphasized the incompleteness of the record and the need to remand the cases. Joining him were fellow conservatives Clarence Thomas and Neil Gorsuch and, to some extent, Barrett and Jackson.

On the other side was Kagan, leaning toward the 11th Circuit’s approach. She wanted to clarify the First Amendment implications when states try to control how platforms filter messages and videos posted by their users. She was generally joined by Chief Justice John Roberts and Justices Sonia Sotomayor and Brett Kavanaugh.

Alito began writing the court’s opinion for the dominant five-member bloc, and Kagan for the remaining four.

Alito goes too far and Barrett flips

But when Alito sent his draft opinion around to colleagues several weeks later, his majority began to crumble. He questioned whether any of the platforms’ content-moderation could be considered “expressive” activity under the First Amendment.

Barrett, a crucial vote as the case played out, believed some choices regarding content indeed reflected editorial judgments protected by the First Amendment. She became persuaded by Kagan, but she also wanted to draw lines between the varying types of algorithms platforms use.

“A function qualifies for First Amendment protection only if it is inherently expressive,” Barrett wrote in a concurring statement, asserting that if platform employees create an algorithm that identifies and deletes information, the First Amendment protects that exercise of editorial judgment. That might not be the situation, Barrett said, for algorithms that automatically present content aimed at users’ preferences.

Kagan added a footnote to her majority opinion buttressing that point and reinforcing Barrett’s view. Kagan wrote that the court was not dealing “with feeds whose algorithms respond solely to how users act online – giving them the content they appear to want, without any regard to independent content standards.”

Jackson then joined much of Kagan’s analysis as well, including that a private company’s collection of third-party content for its platform could itself be expressive and therefore subject to First Amendment considerations when a state attempts to regulate. She added in a concurring statement, “Not every potential action taken by a social media company will qualify as expression protected under the First Amendment.”

In Kagan’s opinion for the majority, she wrote, “Deciding on the third-party speech that will be included in or excluded from a compilation—and then organizing and presenting the included items—is expressive activity of its own. And that activity results in a distinctive expressive product.”

“When the government interferes with such editorial choices—say, by ordering the excluded to be included— it alters the content of the compilation,” Kagan added. “And in so doing—in overriding a private party’s expressive choices—the government confronts the First Amendment.”

Plainly irked by the turn of events, Alito wrote in his final concurring opinion that Kagan’s First Amendment pronouncements amounted only to “nonbinding dicta” that lower courts need not follow.

Such lines between core principles of a decision, or mere dicta, are often fuzzy and the source of disagreement among lower court judges – and even the justices themselves. But, despite Alito’s protest, Kagan had a majority signing her decision, which, at minimum, offers lower court judges a strong indication of the framework the high court majority would use in future online challenges.

Alito had the backing of only two justices in the end, Thomas and Gorsuch. He expressed sympathy for state efforts to restrict what, in an earlier phase of the Texas case Alito called “the power of dominant social media corporations to shape public discussion of the important issues of the day.”

In his separate July 1 opinion for a minority, Alito pointed up why states might want to regulate how platforms filter content: “Deleting the account of an elected official or candidate for public office may seriously impair that individual’s efforts to reach constituents or voters, as well as the ability of voters to make a fully informed electoral choice. And what platforms call ‘content moderation’ of the news or user comments on public affairs can have a substantial effect on popular views.”

Like Oldham, Alito took jabs at the “sophisticated counsel” who challenged the state regulations.

With the Supreme Court having ruled, lower court judges now must explore the scope of the laws on the functions of various platforms, websites and apps. Litigation on this issue will surely continue and someday return to the Supreme Court.

Another Texas setback for Alito

The give and take among the justices in the social media cases took until the very last day of the term. A few weeks before then, the separate majority Alito had tentatively won in the dispute over an alleged retaliatory arrest in Texas fell apart because of how extensively he wanted the court to rule.

The case was brought by Sylvia Gonzalez, a former Castle Hills councilwoman who sued the mayor after she was arrested for removing a public document at a meeting. She said the arrest was in retaliation for speaking out against the city manager and noted that no one else had ever been arrested in such a situation.

The 5th Circuit rejected Gonzalez’s claim, emphasizing that officers had probable cause to arrest her. Gonzalez, the appeals court had ruled, did not qualify for an exception to the wide deference courts give officers who have probable cause because she failed to demonstrate police had declined to make arrests in similar situations.

When the justices voted on the case in March, the majority agreed that the 5th Circuit erred in the standard it used. Alito was assigned the opinion.

But as he began writing, he went further than the other justices in his review of Gonzalez’s case. Alito and his colleagues realized he couldn’t “hold five,” as the expression goes, for a majority.

A new majority agreed to dispatch the case with a limited rationale in unsigned opinion. Rejecting the 5th Circuit’s reasoning, the Supreme Court said the 5th Circuit had applied an “overly cramped view” of the court’s precedent for when people may sue for First Amendment retaliation claims. The high court noted that Gonzalez could not show evidence of whether officers handled similar situations differently because her situation, involving the alleged removal of a document, was exceedingly rare.

The court’s narrow opinion did not suggest how Gonzalez would ultimately fare as she continued the lawsuit.

Alito, in what became a concurring statement signed by him alone, agreed that the 5th Circuit had taken “an unduly narrow view,” but his opinion went further to detail Gonzalez’s actions and explore weaknesses in her varied arguments. Alito’s 16-page concurring opinion would have made it more difficult for Gonzalez to press her range of claims than the five-page opinion that garnered the new majority.

On June 20, when the chief justice announced the opinion in Gonzalez v. Trevino, Alito’s chair at the bench was empty. Alito missed that day, as a total four opinions were handed down, and the next, June 21, when the justices released five other opinions.

Justices sometimes skip one of these final days of the annual session, but usually there’s an obvious reason for the absence, such as travel to a previously scheduled speech. Court officials declined to provide any explanation.

Alito returned for the final four announcement days of the term, yet sometimes appeared preoccupied. On the last day, when Kagan announced the decision in the NetChoice case, Alito was reading through material he had brought along to the bench.

Alito appeared weary of it all by that last day. At 74, he is the second oldest of the current nine, after 76-year-old Thomas. While Alito is still relatively young as far as justices go (most in recent years haven’t left the bench until their 80s), he has reflected in private about retirement.

If Republican Trump were to win Alito may be persuaded to step down. If he does, Trump could look to the 5th Circuit, where many of his most conservative appellate-bench choices from his first term sit, including Alito’s former clerk, Judge Oldham.

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