LOS ANGELES DAILY JOURNAL
THURSDAY, MAY 14, 2026 • PAGE 5
The OpenAI trial and the end of ‘informal’ communications
By James S. Rubinowitz T he most important evi- dence in the dispute be- tween Elon Musk and OpenAI is not a contract, a board resolution or a corporate char- ter. It is a handwritten journal. As reported by the Daily Jour- nal, lawyers in federal court in Oak- land have spent days walking jurors through diary entries written by OpenAI cofounder Greg Brockman during the company’s transformation from a nonprofit research lab. In one November, 2017 entry, Brockman wrote that he was “wrong to steal the nonprofit from [Musk] to convert to b corp without him.” In another, he wrote that “[Musk’s] story will cor- rectly be that we weren’t honest with him in the end about still wanting to do for profit just without him.” Those writings are now courtroom exhibits. So are private texts, Slack messages, emails and internal chats exchanged over nearly a decade among some of the most influential people in technology. The formal corporate record has become almost secondary. U.S. District Judge Yvonne Gon- zalez Rogers dismissed Musk’s fraud and constructive fraud claims before trial. What remains in front of the nine-person advisory jury are claims for breach of charitable trust and unjust enrichment, with Musk seeking up to $150 billion in damages directed to OpenAI’s charitable arm. Those claims depend heavily on what the participants actually believed and communicated privately at the time. The OpenAI litigation is becom- ing a public demonstration of how modern discovery works in practice. Executives still tend to separate “of- ficial” communications from informal ones. Courts increasingly do not. In many high-stakes cases, informal communications become the case. The evidence shaping the narra- tive here did not come from carefully drafted resolutions or polished board memoranda. It came from late night texts, internal Slack discussions and personal reflections exchanged be- tween executives who assumed they were speaking candidly and privately. Musk’s 2022 message to Sam Alt- man, sent after Microsoft’s $10 billion investment pushed OpenAI to a $20 billion valuation, called the arrange- ment a “bait and switch.” Altman’s response: “I agree it feels bad.” A 2016 Musk email to a Neuralink col- league conceded that setting OpenAI up as a nonprofit “might, in hindsight, have been the wrong move.” Brock-
OpenAI, Inc. , Magistrate Judge Ona Wang ordered OpenAI to preserve and segregate all consumer ChatGPT output logs going forward, an order that affected over 400 million users and was upheld on appeal by U.S. District Judge Sidney Stein. By No- vember, the court ordered OpenAI to produce 20 million de-identified chat logs to plaintiffs in the consolidated MDL. That issue is going to grow quickly. Hundreds of millions of people now use AI systems for strategic advice, emotional reflection, drafting sensi- tive communications and just about everything in between. Many appear to assume those conversations carry some practical expectation of con- fidentiality. In most circumstances, they do not. Attorney-client privilege does not apply because the chatbot is not act- ing as legal counsel. No recognized evidentiary privilege automatically shields these exchanges from discov- ery. What users often experience as an intimate or temporary interaction may ultimately exist as a searchable, timestamped business record gov- erned by platform retention policies and discoverable through subpoena. The Brockman journal became a defining exhibit because it captured what a key executive privately be- lieved before litigation existed. AI conversations present the same issue in digital form, except at vastly great- er scale. For the business world, the lesson from the OpenAI trial is not simply that discovery has expanded. It is that the distinction between formal and informal communication is disap- pearing. The communications people create casually, emotionally or impul- sively are increasingly the ones that matter most once litigation begins. James S. Rubinowitz is a product liability litigator and a lecturer at the Cardozo School of Law in New York on the use of AI in trial advocacy.
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vation guidance and standard sub- poena language to expressly cover ephemeral and collaborative messag- ing tools. Deputy Assistant Attorney General Manish Kumar warned that failures to produce such communi- cations could result in obstruction of justice charges. Courts have backed those warn- ings up. In re Google Play Store An- titrust Litigation, U.S. District Judge James Donato sanctioned Google in March 2023 after finding the compa- ny “intended to subvert the discovery process” by allowing employee chats to auto delete every 24 hours despite an active litigation hold. The Securi- ties and Exchange Commission has imposed more than $2 billion in pen- alties on financial institutions since
man’s journal entries, capturing his own private calculations about how to restructure the company without Musk, contradict the public facing story OpenAI told for years. Today, you would be foolish to ex- pect these communications would not end up in the evidentiary record. Not long ago, that assumption looked very different. Over the last several years, reg- ulators and courts have made clear that communications on Slack, Sig- nal, Microsoft Teams, WhatsApp and similar platforms carry the same preservation obligations as tradition- al business records. On Jan. 26, 2024, the Department of Justice’s Antitrust Division and the Federal Trade Com- mission jointly updated their preser-
pared through layers of review. That dynamic explains why the OpenAI trial has focused so heavily on personal communications rather than corporate formalities. The sur- viving claims are largely about intent, reliance and alleged deception. Infor- mal communications are where those issues live. The next stage of this problem is already emerging in federal courts: AI conversations themselves. As generative AI systems become integrated into daily work and per- sonal decision-making, litigants are beginning to confront discovery questions surrounding chatbot inter- actions, prompt histories and AI-gen- erated communications. In May 2025, in The New York Times Company v.
2021 for failing to preserve off-chan- nel business communications, with combined regulatory fines from the SEC, CFTC and FINRA now exceed- ing $3.5 billion. Many executives still treat informal messaging as functionally disposable. Legally, that assumption has col- lapsed. The reason these communications matter so much is straightforward. They capture intent in real time. For- mal documents are drafted with regu- lators, shareholders and future scru- tiny in mind. Private communications usually are not. Jurors understand that instinctively. They tend to view contemporaneous private messages as more reliable indicators of motive and credibility than documents pre-
San Diego State to pay $300k to settle Title IX athletics suit
SUBMIT A COLUMN The Daily Journal accepts opinion pieces, practice pieces, book reviews and excerpts and personal essays. These articles typically should run about 1,000 words but can run longer if the content warrants it. For guidelines, e-mail legal editor Diana Bosetti at diana_bosetti@dailyjournal.com. WRITE TO US The Daily Journal welcomes your feedback on news articles, commentaries and other issues. Please submit letters to the editor by e-mail to diana_ bosetti@dailyjournal.com. Letters should be no more than 500 words and, if referencing a particular article, should include the date of the article and its headline. Letters may not reference a previous letter to the editor.
compliance in higher education. Jenna Rangel and Amber Eck of Haeggquist & Eck LLP in San Diego, Arthur Bryant of Arthur Bryant Law in Oakland, Lori Bull- ock of Bullock Law PLLC in Des Moines, Iowa, and Gayle Blatt and David Casey of Casey Gerry Fran- cavilla Blatt LLP in San Diego rep- resented the plaintiffs.
Title IX litigation involving col- legiate athletics has focused on participation opportunities, athlete treatment, resource allocation and scholarship funding. The San Diego State case is among a series of lawsuits alleging scholarship disparities in college athletics programs and reflects continuing scrutiny of Title IX
Ashley N. Higginson, Brian M. Schwartz, Erika L. Giroux and Scott R. Eldridge of Miller Can- field PLC, Jennifer L. Santa Maria of Ogletree Deakins and Jodi L. Cleesattle of the California Attor- ney General’s Office represented the defense.
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distribution and program resources. Plaintiffs filed the lawsuit during the COVID-19 pandemic, when college athletics programs nation- wide faced operational and finan- cial pressures. The case proceeded through investigation, discovery, motion practice and settlement ne- gotiations before resolution.
douglas_saunders@dailyjournal.com
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