Google Might Be Next to Settle With Trump

Of all the titans of social media, Google CEO Sundar Pichai tried to keep the groveling to a minimum after Donald Trump won last year. He did not, like Meta CEO Mark Zuckerberg, go on podcasts to praise the benefits of “masculine energy” or hire the new president’s close friend, the Ultimate Fighting Championship boss Dana White, to his board of directors. He did not, like the X owner Elon Musk, go to work in the White House or publicly declare his straight-man “love” for Trump. Unlike TikTok CEO Shou Zi Chew, Pichai never pushed a notification to all app users (with an exclamation point!) thanking Trump for his efforts.

There was instead a brief visit to Mar-a-Lago, the requisite $1 million Google donation to Trump’s inaugural fund, and the stoic appearance as a background prop during the ceremony in the U.S. Capitol rotunda. Even Pichai’s statement that day read dutiful and dry: “We look forward to working with you to usher in a new era of technology + AI innovation that will benefit all Americans.”

But the man who runs YouTube may soon get another opportunity to demonstrate his fealty. Trump sued Zuckerberg, Pichai, and the former CEO of Twitter (which Musk later purchased and renamed X) in 2021 for restricting his accounts after the January 6 attack on the U.S. Capitol. The president alleged that the companies and executives had illegally censored him at the urging of U.S. political leaders, violating his First Amendment rights. It was an ironic argument from a politician who likes to settle political grudges with governmental threats. But it was an effective one: During their postelection courtships of Trump, Zuckerberg settled his case with a payment of $25 million, mostly to Trump’s presidential-library fund, and Musk followed with $10 million more.

Read: Why Meta is paying $25 million to settle a Trump lawsuit

Now it may be Pichai’s turn. Lawyers for President Trump and Pichai have begun “productive discussions” about the next steps of the case against YouTube, “with additional discussions anticipated in the near future,” according to briefs filed in a San Francisco federal court shortly after Memorial Day that appear to have escaped public notice. The parties have asked the judge to give them until September 2 to come to an agreement on a path forward.

“I can’t talk about that,” John Cole, a lawyer in the case for Trump, told me when I called to ask about settlement talks. José Castañeda, a spokesperson for Google, also declined to comment.

The fact that the talks are happening at all says more about Trump’s remarkable use of presidential power than his legal prowess or the merits of his case. In 2022, a federal district court dismissed Trump’s case against X  after concluding that Trump had failed to “plausibly allege” that Twitter’s decision to ban his account was directed by the government. Trump’s case against YouTube was put on hold while Trump appealed the X case to the Ninth Circuit, which appeared likely to rule against Trump again.

But Musk’s decision to settle his case while he was working alongside Trump in the White House prevented the appeals court from issuing a decision, and effectively reopened the YouTube case this spring. That has left Pichai with a difficult choice: continue with a legal fight he may win on the merits and risk the wrath of the president of the United States, or agree to give some money to Trump’s presidential library and move on.

The whole situation is head-spinning: Trump has shown that he can successfully use the powers of his elected office to threaten private companies into settling civil suits even when the cases are based on the allegation that those same companies broke the law by caving to the demands of politicians like him.

“Essentially, what this means is that the English language has failed us,” Robert Corn-Revere, the general counsel of the free-speech group Foundation for Individual Rights and Expression, told me. “We need a stronger word than hypocrisy to describe these kinds of activities.”

The incoherence of Trump’s position on the First Amendment has become clear as he has used the power of his office to target the speech of political foes at universities and law firms and incompliant media outlets such as the Associated Press, while simultaneously condemning the very idea that the government should ever try to restrict the speech of his political allies. When the contradiction is pointed out, he dismisses it. His advisers push back fiercely. For Trump, what matters is winning.

“The idea that President Trump is infringing on the First Amendment is a joke,” White House Press Secretary Karoline Leavitt told me in a statement. “This story should be about how pitiful it was for Big Tech to censor the former President of the United States—not the other way around. The President is holding these powerful and wealthy institutions accountable for their years of wrongdoing.”

Legal observers suggest another way of looking at Trump’s approach to free speech. “‘I will support my friends and go after the people who oppose me,’” Raymond Brescia, an associate dean at Albany Law School, told me. “It’s hard to look at it any other way.”

About three months after he took office, Trump alleged during an Oval Office signing ceremony that the Biden administration had illegally launched Internal Revenue Service investigations into his supporters because of their political views. “We’re finding that many people, just having to do with Trump support, have gone through hell,” he said. “It’s a very illegal thing to do what they did.”

I was in the room that day, and I asked Trump how he squared that concern with his decision to entertain changing Harvard University’s tax status because he did not like its diversity policies and its handling of on-campus protests. He quickly pivoted. “Because I think Harvard is a disgrace. I think what they did was a disgrace,” he said. Harvard, of course, has asked a court to rule that Trump’s various punishments violate the First Amendment.

This week’s settlement by Paramount Global, the parent company of CBS News, offers further evidence of his mindset. Before the 2024 election, Trump filed a lawsuit against CBS Broadcasting Inc. alleging that the network had violated the Texas Deceptive Trade Practices Act by choosing to air two different edits, on two different shows, of Vice President Kamala Harris’s answer to a question. Such editing is a routine part of political journalism, which regularly shortens quotes and tapes for brevity. Trump argued that the version that aired for a larger audience on 60 Minutes made Harris look deceptively better because it left out some of her confusing stammering.

Rather than wait for the courts to address the merits of his claim, he applied his own pressure once he regained government power. Trump’s new chair of the Federal Communications Commission, Brendan Carr, reopened a closed complaint alleging that the editing amounted to “news distortion.” Carr had previously said that the claim should be considered when the FCC weighed approval of the proposed merger of Paramount Global and its new investor, Skydance. Trump egged Carr on. In a post complaining about a different 60 Minutes segment in April, Trump wrote that he hoped Carr would “impose the maximum fines and punishment” on CBS. Paramount agreed on Tuesday to give $16 million to Trump’s presidential library to settle the Harris-interview case. Trump’s presidential-library foundation, which incorporated in Florida in May, has not yet disclosed its plans for what to do with all the settlement money. Trump’s son Eric Trump, his son-in-law Michael Boulos, and an attorney for the Trump Organization, James Kiley, have been named the initial trustees.

All the while, the Trump administration has continued to ceremoniously embrace the First Amendment rights of American companies and citizens. On his first day in office, Trump issued an executive order called Restoring Freedom of Speech and Ending Federal Censorship, which condemned the Biden administration for “exerting substantial coercive pressure” on social-media companies to moderate posts on their sites. Trump declared that it was now the policy of the United States to “ensure that no Federal Government officer, employee, or agent engages in or facilitates any conduct that would unconstitutionally abridge the free speech of any American citizen.”

“There is a new sheriff in town,” Vice President J. D. Vance declared on February 14 in Munich, Germany. “And under Donald Trump’s leadership, we may disagree with your views, but we will fight to defend your right to offer them in the public square, agree or disagree.”

Vance didn’t mention that just three days earlier, Leavitt had told an Associated Press reporter that, at Trump’s direction, the AP would lose its permanent spot in the White House press pool, barring it from the Oval Office and Air Force One, until the wire service started referring to the Gulf of Mexico as the “Gulf of America.” A district-court judge ruled that this decision violated the First Amendment rights of the AP, though the ruling was later paused by an appellate court after the White House imposed broader changes on how the pool system is organized. The AP, which has not bowed to Trump’s demands and has yet to regain its spot, has since been let into the pool on occasion and continues to have access to White House briefings.

The courts have not been impressed by such misdirection. Just three months after Trump’s executive order barring unconstitutional abridgment of free speech, D.C. federal district Judge Beryl A. Howell ruled that Trump had committed that exact offense. At issue was a March 6 executive order, 14230, that declared that employees of the law firm Perkins Coie should be limited from entering federal buildings, interacting with federal employees, or holding security clearances because of the firm’s “dishonest and dangerous”activity, including the decision to represent Hillary Clinton during her 2016 presidential campaign and to promote diversity in its hiring practices. Three other federal judges have since thrown out Trump executive orders targeting three more law firms on the same grounds.

Read: A reality check for tech oligarchs

“In a cringe-worthy twist on the theatrical phrase ‘Let’s kill all the lawyers,’ EO 14230 takes the approach of ‘Let’s kill the lawyers I don’t like,’ sending the clear message: lawyers must stick to the party line, or else,” Judge Howell explained while voiding the executive order. Trump appealed Howell’s ruling this week to the D.C. Circuit.

Should Pichai choose to fight it out in court with Trump, he would quite possibly get a favorable ruling. When the Ninth Circuit heard the X case in 2023, two of the three judges on the panel questioned the evidence that Trump had gathered to suggest that his ban from Twitter had been caused by government pressure. As in the YouTube case, Trump’s lawyers had presented only general comments from public officials about the need for social-media companies to increase moderation, including from members of the House and Senate, then-candidates Joe Biden and Kamala Harris, and former first lady Michelle Obama.

“Why do statements from, let’s say, four senators at a committee hearing all of a sudden commit all of the power of the federal government to create state action here?” Ninth Circuit Judge Jay Bybee, an appointee of President George W. Bush, asked during oral arguments in the case. “I don’t know of any case that stands for that proposition.”

The problem for Pichai is different, of course, as it was for Zuckerberg, Musk, and Paramount—and will be different for anyone else Trump targets. Google could end up losing more by prevailing in court than it would win by conceding the case and making an eight-figure donation to Trump’s presidential library.