Google employees liberally labeled their emails as “privileged and confidential” and spoke “off the record” over chat messages, even after being told to preserve their communications for investigators, lawyers for the Justice Department have told a Virginia court over the past couple of weeks.

That strategy could backfire if the judge in Google’s second antitrust trial believes the company intentionally destroyed evidence that would have looked bad for it. The judge could go as far as giving an adverse inference about Google’s missing documents, which would mean assuming they would have been bad for Google’s case.

Documents shown in court regularly display the words “privileged and confidential” as business executives discuss their work, occasionally with a member of Google’s legal team looped in. On Friday, former Google sell-side ad executive Chris LaSala said that wasn’t the only strategy Google used. He testified that after being placed on a litigation hold in connection with law enforcers’ investigation, Google chat messages had history off by default, and his understanding was that needed to be changed for each individual chat that involved substantive work conversations. Multiple former Google employees testified to never changing the default setting and occasionally having substantive business discussions in chats, though they were largely reserved for casual conversations.

LaSala also used that default to his advantage at times, documents shown by the government in court revealed. In one 2020 chat, an employee asked LaSala if they should email two other Google employees about an issue and, soon after, asked, “Or too sensitive for email so keep on ping?” LaSala responded, instructing the employee to “start a ping with history turned off.” In a separate 2020 exchange, LaSala again instructed his employee to “maybe start an off the record ping thread with Duke, you, me.” 

“It was just how we spoke. Everyone used the phrase ‘off the record ping,’” LaSala testified. “My MO was mostly off the record, so old tricks die hard.”

Still, LaSala said he “tried to follow the terms of the litigation hold,” but he acknowledged he “made a mistake.” Shortly after a training about the hold, he recalled receiving a chat from a colleague. Though LaSala said he turned history on, he wasn’t sure the first message would be preserved. LaSala said he put that message in an email just in case. In general, LaSala said, “We were really good at documenting … and to the extent I made a mistake a couple times, it was not intentional.”

Brad Bender, another Google ad tech executive who testified earlier in the week, described conversations with colleagues over chat as more akin to “bumping into the hall and saying ‘hey we should chat.’” The DOJ also questioned former Google executive Rahul Srinivasan about emails he marked privileged and confidential, asking what legal advice he was seeking in those emails. He said he didn’t remember.

Google employees were well aware of how their written words could be used against the company, the DOJ argued, pointing to the company’s “Communicate with Care” legal training for employees. In one 2019 email, Srinivasan copied a lawyer on an email to colleagues about an ad tech feature and reminded the group to be careful with their language. “We should be particularly careful when framing something as a ‘circumvention,’” he wrote. “We should assume that every document (and email) we generate will likely be seen by regulators.” The email was labeled “PRIVILEGED and CONFIDENTIAL.”

While the many documents shown by the DOJ demonstrate that Google often discussed business decisions in writing, at other times, they seemed to intentionally leave the documentation sparse. “Keeping the notes limited due to sensitivity of the subject,” a 2021 Google document says. “Separate privileged emails will be sent to folks to follow up on explicit [action items].”

“We take seriously our obligations to preserve and produce relevant documents,” Google spokesperson Peter Schottenfels said in a statement. “We have for years responded to inquiries and litigation, and we educate our employees about legal privilege. In the DOJ cases alone, we have produced millions of documents including chat messages and documents not covered by legal privilege.”

The judge in Google’s first antitrust battle with the DOJ over its search business declined to go as far as an adverse inference, even though he ruled against Google in most other ways. Still, he made clear he wasn’t “condoning Google’s failure to preserve chat evidence” and said, “Any company that puts the onus on employees to identify and preserve relevant evidence does so at its own peril. Google avoided sanctions in this case. It may not be so lucky in the next one.”