In late 2008, as Google faced antitrust scrutiny over an advertising deal with its rival Yahoo and confronted lawsuits involving patent, trademark and copyright claims, its executives sent out a confidential memo.

“We believe that information is good,” the executives told employees in the memo. But, they added, government regulators or competitors might seize on words that Google workers casually, thoughtlessly wrote to one another.

To minimize the odds that a lawsuit could flush out comments that might be incriminating, Google said, employees should refrain from speculation and sarcasm and “think twice” before writing one another about “hot topics.” “Don’t comment before you have all the facts,” they were instructed.

The technology was tweaked, too. The setting for the Mountain View-based company’s instant messaging tool was changed to “off the record.” An incautious phrase would be wiped the next day.

The memo became the first salvo in a 15-year campaign by Google to make deletion the default in its internal communications. Even as the internet giant stored the world’s information, it created an office culture that tried to minimize its own. Among its tools: using legal privilege as an all-purpose shield and imposing restraints on its own technology, all while continually warning that loose lips could sink even the most successful corporation.

How Google developed this distrustful culture was pieced together from hundreds of documents and exhibits, as well as witness testimony, in three antitrust trials against the Silicon Valley company over the last year. The plaintiffs — Epic Games in one case, the Department of Justice in the other two — were trying to establish monopoly behavior, which required them to look through emails, memos and instant messages from hundreds of Google engineers and executives.

The exhibits and testimony showed that Google took numerous steps to keep a lid on internal communications. It encouraged employees to put “attorney-client privileged” on documents and to always add a Google lawyer to the list of recipients, even if no legal questions were involved and the lawyer never responded.

Companies anticipating litigation are required to preserve documents. But Google exempted instant messaging from automatic legal holds. If workers were involved in a lawsuit, it was up to them to turn their chat history on. From the evidence in the trials, few did.

Google is far from the only company trying to keep newer forms of communication out of the courtroom. As instant messages and text messages have become popular office tools, corporations and regulators have increasingly clashed over how the missives can be used in court.

A generation ago, a water-cooler conversation or a phone call might have been incriminating, but the words would have dissolved in the air. Someone might remember them, but they could always be denied. Perhaps listeners misheard or misunderstood.

Companies would like instant messages to be as ephemeral as a real-life conversation. A comment made by text to a subordinate about the implications of a merger is just so much chatter, they argue. But regulators, and litigants, see them as fair game.

In August, the Federal Trade Commission, which is suing to stop a $25 billion supermarket merger between Albertsons and Kroger, said several Albertsons executives had demonstrated “a pervasive practice” of deleting business-related text messages in defiance of legal requirements to keep them.

Some of these texts, the F.T.C. argued, suggested that at least one executive thought prices might increase as a result of the merger. The judge said Albertsons “failed to take reasonable steps” to preserve the messages, but did not punish the chain. Albertsons declined to comment.

In April, the F.T.C. said in a legal filing as part of its antitrust case against Amazon that company executives had used the disappearing message tool Signal to discuss competition issues, even after they were required to keep all communications in the case. Amazon said the assertions that it had destroyed information were “baseless and irresponsible.”

But Google has faced the broadest criticism for its actions, with the judges in all three antitrust cases chastising the company for its communications practices.

Judge James Donato of the U.S. District Court for the Northern District of California, who presided over the Epic case, said that there was “an ingrained systemic culture of suppression of relevant evidence within Google” and that the company’s behavior was “a frontal assault on the fair administration of justice.” He added that after the trial, he was “going to get to the bottom” of who was responsible at Google for allowing this behavior. Judge Donato declined to comment.

Judge Leonie Brinkema of the U.S. District Court for the Eastern District of Virginia, who is overseeing Google’s antitrust case involving advertising technology, said at a hearing in August that the company’s document retention policies were “not the way in which a responsible corporate entity should function.” She added, “An awful lot of evidence has likely been destroyed.”

The Justice Department has asked Judge Brinkema for sanctions, which would be a presumption that the missing material was unfavorable to Google on the issues it is on trial for, including monopoly power and whether its conduct was anticompetitive. Closing arguments in the case are scheduled for Monday.

In a statement, Google said it took “seriously our obligations to preserve and produce relevant documents. We have for years responded to inquiries and litigation, and we educate our employees about legal privilege.” The company said it had provided “millions of documents” in the Justice Department cases alone.

From Google’s point of view, it was the Marie Kondo of corporations, merely tidying up its records and files. But it did this so comprehensively and obsessively that it created the illusion of deceit that it was trying so hard to dispel, said Agnieszka McPeak, a professor at Gonzaga University School of Law who has written about evidence destruction.

“Google had a top-down corporate policy of ‘Don’t save anything that could possibly make us look bad,’” she said. “And that makes Google look bad. If they’ve got nothing to hide, people think, why are they acting like they do?”

Microsoft’s Long Shadow

Google was founded in September 1998, a few months after the era’s most dominant tech company — Microsoft — was sued by the Justice Department for antitrust violations. Seeking to show that Microsoft was illegally monopolizing the web browser market, the department did not have to look far for damning memos.

“We need to continue our jihad next year,” a company vice president wrote to Microsoft’s chief executive, Bill Gates, in one memo. Another executive, trying to persuade Apple to kill a feature, said, “We want you to knife the baby.”

Microsoft lost the case, though the verdict was partly overturned on appeal. Still, it was enough of a near-death experience to make the next generation of tech companies, including Google, wary of both documents and loose comments.

The trouble was, technology made it so very easy to produce and preserve an abundance of both. Google produced 13 times as many emails as the average company per employee did before it was a decade old, Kent Walker, Google’s top lawyer, testified in the Epic trial. Google felt overwhelmed, he said, and it was clear to the company that things would only become worse if changes weren’t made.

The 2008 memo that said chat messages would be automatically purged was signed by Walker and Bill Coughran, an engineering executive. They noted that Google had “an email and instant messaging culture.” Its instant messaging tools, first called Talk, later Hangouts and then Chat, were quickly taken up by employees.

Chat was where engineers could go a little wild, safely. As one Googler wrote in a chat that surfaced as a courtroom exhibit, the need to be cautious “makes for less interesting, sometimes even less useful written communication. But that’s why we have off-the-record chats.”

Google, like many corporations, deals with so many lawsuits that some employees are subject to multiple litigation holds at the same time. A few may be on litigation holds for their entire career.

Lauren Moskowitz, an Epic lawyer, asked Walker during his testimony in the case how putting employees in control of the process actually worked.

“You expected your employees, hundreds, thousands of employees, to stop what they were doing for every instant message that they ever sent or received every day, and parse through a list of topics on some legal hold, to decide whether they should take an action to change a default setting in their Chat before conducting the rest of their business,” Moskowitz said.

Walker responded that the policy had been “reasonable at the time.”

As Google became bigger, its vocabulary became smaller. In a memo from 2011 titled “Antitrust Basics for Search Team,” the company recommended avoiding “metaphors involving wars or sports, winning or losing,” and rejecting references to “markets,” “market share” or “dominance.”

In a subsequent tutorial for new employees, Google said even a phrase as benign as “putting products in the hands of new customers” should be avoided because it “can be interpreted as expressing an intent to deny consumers choice.”

If using the right words and deleting messages did not keep Google out of the courthouse, the company concluded, invoking the lawyers would.

In the Epic case, the plaintiff contended that Google’s many evocations of attorney-client privilege were merely for show, to keep the documents out of the courtroom. Sundar Pichai, Google’s chief executive, wrote in one 2018 email to another executive, “Attorney Client Privileged, Confidential, Kent pls advice,” referring to Walker. The email, about a nonlegal issue, was withheld by Google and stripped of its privilege only after Epic challenged it.

Walker was asked to explain Google’s behavior to the judge. He denied that there was “a culture of concealment” but said one problem was Googlers unsure of the meaning of certain words.

“They think of the word ‘privilege’ as similar to ‘confidential,’” he said.

A message surfaced in the Epic trial in which a Google lawyer identified the practice of copying lawyers on documents as “fake privilege” and seemed rather amused by it. Walker said he was “disappointed” and “surprised” to hear that term.

The jury hearing the case ruled in favor of Epic on all 11 counts in December.

Google declined to provide Pichai and Walker for comment. Last month, three advocacy groups, led by the American Economic Liberties Project, asked for Walker to be investigated by the California State Bar for coaching Google to “engage in widespread and illegal destruction” of documents relevant to federal trials.

‘What Happens in Vegas’

In September 2023, as Google went on trial in an antitrust case over its dominance in internet search, the Justice Department asserted that the company had withheld tens of thousands of documents, saying they were privileged. When the documents were reviewed by the court, they were deemed not privileged after all.

“The court is taken aback by the lengths to which Google goes to avoid creating a paper trail for regulators and litigants,” Judge Amit P. Mehta of the U.S. District Court for the District of Columbia wrote. Google, he noted, had clearly learned Microsoft’s lesson: It had effectively trained its employees not to create “bad” evidence.

Judge Mehta said it ultimately did not matter: In August, he found Google guilty of being a monopoly. Still, he said, he did not think the company was behaving well.

“Any company that puts the onus on its employees to identify and preserve relevant evidence does so at its own peril,” he wrote, adding that Google might not be so lucky to avoid sanctions in the next case.

The next case arrived in September, when the Justice Department argued in Judge Brinkema’s courtroom in Virginia that Google had built a monopoly in the highly profitable technology that served online ads.

Exhibits in the cases showed that Googlers had learned to be a little paranoid for the good of Google and their own careers. Talk in the dark, they insisted over and over, rather than in the light.

“How do we turn History off?” Adam Juda, a vice president for product management, wrote in a 2020 chat. “I don’t do History on 🙂.”

Sometimes executives were so worried about leaving a record that they defaulted to obsolete technology.

In 2017, Robert Kyncl, then the chief business officer at the Google subsidiary YouTube, asked his boss, Susan Wojcicki, if she had a fax machine at home. Kyncl explained he had a “privileged doc” and “just didn’t want to send email.” Wojcicki, who died in August, did not have a fax machine.

If employees wanted to keep an electronic record, they were rebuked. In a group chat from 2021, one employee inquired: “ok for me to keep history on here? need to keep some info for memory purposes.”

Not OK, said Danielle Romain, the vice president of Trust, a Google team that looks for solutions that enhance user privacy and trust. “The discussion that started this thread gets into legal and potentially competitive territory, which I’d like to be conscientious of having under privilege,” she said. “I’d like to stick to the default of history off.”

Julia Tarver Wood, a Justice Department lawyer, said at an August hearing in the ad-tech case that Google employees “referred to these off-the-record chats as ‘Vegas.’ What happens in Vegas stays in Vegas.”

Google maintained that it did its best to provide the government with the documents it could, and that, in any case, the Justice Department did not establish that the deleted conversations were crucial to its case. The Justice Department said it could not do that because the material had been deleted.

Regulators have recently underlined that there is no “Vegas” in chats. This year, the F.T.C. and the Justice Department’s antitrust division made it “crystal clear” in an enforcement memo: Communications through messaging apps are documents and must be preserved if there is threat of litigation.

Last year, Google changed its procedures. The default became saving everything, including chats. Employees on litigation holds can no longer turn chat history off.

Old habits die hard, however. In one chat, employees responded to the news by forming a group to secretly communicate on WhatsApp, Meta’s secure messaging app.

David Streitfeld is a reporter with The New York Times. Copyright 2024, The New York Times.