14 Deliverance
In the weeks before Sutskever reached out to Toner, Altman was dealing with a PR crisis. After years of his sister’s estrangement and her turn to sex work staying out of the media, her story had finally burst into the open.
On September 25, 2023, Elizabeth Weil, a features writer at New York magazine, published a profile of Sam Altman that for the first time in the mainstream press referenced Annie’s existence. Weil juxtaposed details of Annie’s life, including her suffering repeated health challenges and living in severe financial duress without housing security, against Sam’s lifestyle featuring multimillion-dollar homes and luxury cars. “Annie Altman?” Weil wrote in her piece. “Readers of Altman’s blog; his tweets; his manifesto, Startup Playbook; along with the hundreds of articles about him will be familiar with Jack and Max…Annie does not exist in Sam’s public life. She was never going to be in the club.”
Altman knew the details were coming. In the lead-up to their publication, which happened during Yom Kippur, the Jewish holiday of atonement, Weil had given OpenAI an opportunity to comment on her reporting; New York had also worked with the company as part of its fact-checking process. The task of facilitating the comment request and trying to control the story had fallen to Hannah Wong, who had become OpenAI’s VP of communications and suddenly found herself as the go-between for the magazine and Altman’s family, wondering if this should really be part of her job.
The final day before the profile’s release, once it was apparent that the details about Annie would be published, Annie had received an email from Sam. “hi annie. in the spirit of it almost being yom kippur, i wanted to apologize and ask for forgiveness for something,” he wrote. During Annie’s requests for support, he had felt caught in the middle, torn between wanting to defer to their mom, agreeing with the rest of the family that Annie should learn financial independence, and feeling that Annie needed medical help and was struggling to function. “still, I made the wrong call and should just have just [sic] kept supporting you; i sincerely apologize,” he said.
The sharp turn from the otherwise glowing public reception that Altman had received since the release of ChatGPT, and having what he viewed as his family’s painful private matters spilling out into the open, weighed on him. The fallout of the piece made it worse. After it came out, old tweets of Annie’s with allegations that Sam had abused her in various ways resurfaced and began to go viral. But as heavy and challenging as it was for Sam, it was an extraordinary release of pain for Annie. For years, in addition to the compounding stress from her health challenges and lack of stability, she felt as if she had been shouting into the void and erased from significance.
In 2024, I would reach out to Annie to better understand her side of the story. I also reached out directly to her mother, Connie Gibstine, to her brothers Max and Jack, and to Sam via OpenAI’s communications team, to seek their account. Annie was eagerly cooperative, hopeful for a platform to finally share personal experiences, which she viewed as crucial to understanding Sam’s moral character. She provided extensive correspondence with her family, physical and mental health records spanning most of her childhood to adulthood, and other corroborating evidence, which charted the fallout she had with the family and the deterioration of her life circumstances.
Gibstine offered a brief statement emphasizing the family’s love for Annie and concern for her well-being while also denying Annie’s claims, which she called “horrible, deeply heartbreaking, and untrue.” Gibstine declined to have a more in-depth conversation or to provide responses to detailed questions seeking her perspective on Annie’s account. She did not respond to my additional requests for documentation to support her own claims. Max and Jack did not respond. OpenAI did not comment on specifics.
In January 2025, after Annie filed her lawsuit against Sam, he, Gibstine, Max, and Jack issued a more forceful public denial of Annie’s allegations, characterizing her as mentally unstable and unreasonably demanding of money, and her claims as having “evolved drastically over time.” “It is especially gut-wrenching when she refuses conventional treatment and lashes out at family members who are genuinely trying to help,” they said.
Through my conversations with Annie and the documentation she provided, a complex picture emerged of the turbulent journey that led her to go public with her allegations on Twitter and in her subsequent lawsuit, as well as with the details of her life she shared for Weil’s profile. I did not have access to the full reasoning behind many of her family’s decisions, and the truth of some of Annie’s allegations, in particular Sam’s alleged sexual abuse of her as a child, is unknowable, but her story became a microcosm to me of the many themes that define the broader OpenAI story. It also helped me solidify my understanding of how much OpenAI is a reflection and extension of the man who runs it. Annie’s persistent efforts to add her perspective to the record quickly turned into a company issue. Coverage of Annie would get under Sam’s skin perhaps more than any other kind of story, pulling Hannah Wong in her capacity as OpenAI’s communications head into his efforts to contain its spread. It also became a company issue in another way: At the time Annie’s allegations first rose to the fore, other OpenAI executives took notice.
In many ways, Annie and Sam, nine years apart, are remarkably similar. Many of the words that people close to Sam use to describe him also shine through in Annie: She is an excellent listener; she remembers the tiniest details about others; she is very goofy, extremely generous, and quick to win people’s trust.
Like Sam, she also excelled in academics. The only other Altman sibling to graduate from Burroughs, she made an impression on her physics teacher, James Roble, who remembers her fondly more than a decade later as a talented student with a sunny demeanor. For college, she went to Tufts University, majoring in biopsychology and minoring in dance. After graduation in 2016, she completed her premed requirements in anticipation of one day going to medical school; she moved to the Bay Area for a research position in a neuroscience lab at the University of California, San Francisco. Before her life went sideways, she was, in other words, a typical profile of an ambitious, well-educated young adult with plenty of options.
But Annie’s circumstances began to unravel after a series of unexpected challenges. While still in college in 2014, she was diagnosed with Achilles tendinitis, a swelling of the tendon that comes from overuse, and a bone spur, putting her in a walking boot. It became the first of a growing laundry list of physical health ailments that would plague her body with chronic pain and, at their peaks, severely limit her mobility and impact her quality of life. In a span of six years, Annie dealt with recurring tonsillitis; recurring pelvic pain; repeated flare-ups in her tendinitis, which placed her in more walking boots, spread beyond her right ankle, and at times made it difficult to even stand for short periods; and a growing number of ovarian cysts that culminated in a diagnosis for polycystic ovarian syndrome, or PCOS, which sometimes caused her to sweat through her sheets at night, a common symptom.
Amid all these health issues, she suffered another paralyzing blow: On May 25, 2018, her dad, with whom she was closest in the family, died of a sudden heart attack.
Annie has dealt with mental health struggles throughout her life. She was diagnosed at a young age with general anxiety and obsessive-compulsive disorder, taking Zoloft for the better part of a decade until a psychiatrist helped her taper off in college. Before her father’s death, she was doing a lot better. She had adopted nonpsychiatric mental health tools, including meditation, and was searching for ways to address the root inflammation that seemed to underlie her repeated physical ailments with a full embrace of a healthy, organic, whole foods diet. Her larger health journey sparked a new interest in alternative medicine, and she took a yoga teacher training. She was leaning into her lifelong love of art and had written a draft of a book she called “The Humanual,” capturing her reflections on life and how to be a good human. Her dad’s death shattered her. It sent her mental health spiraling and seems to have marked an accelerated degradation in her physical health. By late 2018, going to various doctors and specialists was becoming routine.
Sam has also spoken publicly about his dad’s death being the worst moment of his life. It happened mere months after Musk stepped down as OpenAI cochair and Sam took over. People close to Sam say the loss sent him reeling. For a while, he behaved erratically and struggled to cope. The death was clearly an inflection point in Annie’s and Sam’s relationship as well as her relationship with the rest of the family. Her connection with them, and her mom in particular, had already been strained over disagreements about her various life decisions, Annie says, including her turn away from a traditional medical career and her choice to stop taking Zoloft in favor of natural coping mechanisms. Her dad had been her sole unequivocal supporter. Without him, she grew isolated from the family yet yearned for their acceptance and support. Instead, after clashes over money, the relationship reached a breaking point.
After her dad’s death in 2018, Annie was living in LA. She was working part time as a writing assistant and then at a marijuana dispensary. Annie says she inherited around $100,000 from her dad’s life insurance. She threw herself deeper into pursuing her love of art and performance as a serious career: She took comedy classes; she went to open mics; she started a podcast; she rewrote the first draft of her book into a one-woman show she renamed The HumAnnie. By mid 2019, the funds were depleting, most of it spent, she says, on her various artistic investments, her high rent, her out-of-pocket health insurance, and her accumulating medical expenses—medical imaging, physical therapy, psychotherapy, Lyfts and Ubers to her appointments.
For Annie, it was what happened next that spelled the beginning of the end of her relationship with her family. In May 2019, as her chronic pain continued, she learned that her dad had left her his 401(k). She quit the dispensary and drew up a six-month plan to use the extra financial runway—a little over forty thousand dollars—to tend to her health and get her creative endeavors off the ground enough to hopefully generate a sustainable source of income. But soon after, her mother, who retained authority over her dad’s retirement funds as the surviving spouse, notified Annie that she would not in fact be receiving the money. The best tax strategy, Gibstine wrote to Annie in an email, was for Gibstine to keep the funds in her name in a tax-deferred account that would pass to Annie via a trust and to which she would gain access at age fifty-nine and a half. “We all want what is best for you, and we believe that what is best for you (and for everyone) is financial independence, which brings long-term satisfaction, personal growth and security,” Gibstine said. “For this reason, we want to clarify that we will not financially support you if/when your current inheritance from Dad runs out.” The email was signed “Mom, Sam, Max, Jack.”
Annie was in a fragile state. Her therapist’s notes from the same period say that the move her family made with the hope of getting her back on her feet instead worsened her condition. In December 2019, her bank account slid into the negative. Sam had secured Microsoft’s first $1 billion investment into OpenAI earlier that year and the company was full speed ahead in training GPT-3. Scared and alone, Annie logged on to an escort service called SeekingArrangement and showed her breasts to a man over a video call for enough money to bring her account out of the red.
Annie says she had never before asked her mother or brothers for financial support. She had not assumed she could rely on their wealth, but neither had she believed they would leave her without a safety net should she truly be in an emergency. From late 2019 to mid-2020, Annie made several appeals to her family for financial help, including once the pandemic added another layer of stress and uncertainty. After Sam and her mother attended two family therapy sessions with her, they agreed to cover her expenses for a part of the year.
In her exchanges with her family, it’s apparent that they were worried that the money could enable harmful behaviors and believed the best way to help her reestablish her mental health was to continue to encourage her financial independence. Both Gibstine’s statement to me and the family’s public one said their actions have been guided by professional advice on how best to support Annie.
In May 2020, as her family’s financial coverage neared its end and Annie continued to struggle, she requested more help to pay for her physical and talk therapy, which she told them was $45 and $15 a session respectively. They declined, saying they believed she should cover her June expenses herself, including with a security deposit returning to her. She packed up her small number of belongings and arrived in Hawai’i, where she had been when her dad made his final visit to her a few months before he’d died. She found a work trade on a farm with light physical tasks like weeding and planting. Sam emailed her for her new address. Eight months after their dad died, he had asked each sibling to mail their mom a lock of hair to be mixed together with their dad’s ashes and turned into a diamond for each of them. They “will mostly be from carbon from dad but will then have a little bit of each of us too,” he’d written. Annie’s diamond was now ready; Sam wanted to send it over.
To Annie, Sam’s email felt like a slap in the face. She didn’t want an expensive diamond; she wanted his help to guarantee her food and housing. She couldn’t tell whether Sam just didn’t get it or didn’t care about the severity of her crisis. The chasm between her, Sam, and the rest of her wealthy family felt irreconcilable. With enormous pain and grief, she stopped speaking with them.
Over the next three years, before Elizabeth Weil reached out to her, Annie’s life bottomed out. She faced housing insecurity, food insecurity, health insecurity; she turned to virtual and physical sex work to pay the bills. In their public statement, the family said they tried “in many ways to support Annie and help her find stability.” In Annie’s retelling, one of those extensions of support came in the spring and summer of 2021, when Sam sought to reconnect with her. They had three phone calls, she remembers, during which he told her how much he loved her and offered to buy her a house. Annie and the family describe that offer differently. Annie says the offer was not for her to own the house but for her to live in it, an arrangement she understood was meant to prevent her from selling the property and which she worried could be another way through which Sam and their mother could impose their views on her health and career decisions. Gibstine said in her statement to me that the family offered Annie home ownership but did not respond to my requests for corroborating documentation. In the family’s public statement, they said they offered to buy Annie a house through a trust, so that she could have a place to live without the ability to sell it immediately. In the end, Sam and Annie reached a different agreement: He would pay her rent for a year directly to her landlord. In the summer of 2022, when she didn’t reestablish contact, the payments stopped.
Annie’s story deepens the dueling portraits that people paint of Sam. He is at once generous and self-serving, agreeable and threatening, a benefactor for so many people and the source of great personal pain for others. Someone who projects sincerity and altruism in public but reveals a more complicated calculus through his behaviors behind closed doors. Someone who can give and take away, leaving many with an impression that they are part of a larger game of chess for which only he can see the full board, and the end game is to preserve his power as king.
Annie’s story also complicates the grand narrative that Sam and other OpenAI executives have painted of AI ushering in a world of abundance. Altman has said that he expects AI to end poverty. Brockman has repeated, through his stories about his friend and his wife, Anna, that AGI will dramatically improve healthcare. Sutskever has said that it will lead to wildly effective, dirt-cheap psychotherapy. And yet, against the reality of the lives of the workers in Kenya, activists in Chile, and Altman’s own sister’s experience bearing the brunt of all of these problems, those dreams ring hollow.
Despite all the leaps and bounds in AI capabilities, none of them helped to alleviate any part of Annie’s desperation. If anything, AI may have served to entrap her further. She hadn’t wanted to turn to sex work. It was, she says, a “plan Z.” When her chronic pain intensified and made even her work trade too difficult, she had first attempted digital means of monetizing her art. She continued her podcast and maintained an Etsy store and Patreon account, but they didn’t earn enough to even cover her phone bill. A strange thing was happening, which she documented in screenshots over time: She was getting little to no exposure across all of her social media. Sometimes she noticed chunks of the reviews on her podcast in the Apple app mysteriously disappearing, which limited its discovery. At least twice, on both her Instagram and YouTube, she would accumulate views and then inexplicably lose them. A former Facebook data scientist and two tech and sex work experts say it’s possible that Annie’s very first SeekingArrangement account in December 2019 could have limited her online traction, based on the nature of how tech platforms track and shadow ban sex workers through automated systems by tagging their devices, emails, bank accounts, or other information that ties together their online presence, even for profiles completely unrelated to their sex work. Seeing no other path forward, Annie went back to SeekingArrangement as well as starting an OnlyFans account, entangling her online presence and access to economic opportunities even more in a web of algorithmic moderation.
Neily Messerschmidt, a former tech industry leader at companies such as Sony who now oversees a wellness division for an organic farm network, met Annie shortly after she moved to the Bay Area in 2016 and worked for a time with the network during her embrace of healthy eating. Over the years, Messerschmidt became a motherly figure as Annie severed ties with her biological family. “Sam carried AI into the world just like he actually treated his young sister,” Messerschmidt says. “He’s just over there thriving, and his sister’s falling through the cracks.”
In late 2020 and early 2021, after Annie estranged herself from the family, she began to experience devastating flashbacks of childhood sexual abuse. In sessions from July 2021 to January 2022 with a new trauma therapist on Maui, the notes chronicle the crisis that Annie went through with the involuntary memories, including intense questioning about her identity. From fifteen sessions, the therapist wrote down her diagnostic impressions: generalized anxiety, PTSD, and a personal history of sexual abuse in childhood.
The notes didn’t reference a specific abuser. But around that time, Annie began regularly calling Messerschmidt, who herself had been raped at nineteen and had noticed early on in her interactions with Annie at the organic farm network the telltale signs of someone with a history of abuse. “She was not comfortable around certain men,” Messerschmidt remembers. “I know someone that’s been abused when I see them. She would basically ask to be out of meetings when certain men were around. She would stand off to the side when they were in the room.”
In intense, emotional conversations, Annie described to Messerschmidt her sudden flashbacks: In these childhood memories, Messerschmidt remembers Annie told her, it was Sam who had repeatedly climbed into her bed, sometimes with Jack, and molested her.
It is important to note that it’s often difficult to prove decades later whether alleged childhood sexual abuse happened, or the details of such abuse. What is known from psychology is one common pattern that some abuse victims suffer: The victim’s brain blocks out any memory of it until a trigger—perhaps puberty, becoming sexually active, or new unwanted sexual advances—involuntarily resurfaces it, a therapist I consulted with says. The body remembers the trauma, even if the mind doesn’t. As Annie got deeper into sex work, she may have suddenly been facing a rush of triggers.
In detailing Annie’s experiences of her flashbacks, as told to Messerschmidt and as reflected in part in the notes of her trauma therapist, the intent is not to determine exactly what happened in Annie’s childhood but to re-create an account of what she experienced and believed as an adult, which ultimately motivated her to speak out.
In November 2021, while Sam was covering her rent, Annie posted publicly for the first time about her allegations. “I experienced sexual, physical, emotional, verbal, financial, and technological abuse from my biological siblings, mostly Sam Altman and some from Jack Altman,” she wrote on Twitter. “I feel strongly that others have also been abused by these perpetrators. I’m seeking people to join me in pursuing legal justice, safety for others in the future, and group healing.”
Her post didn’t gain traction. She was a nobody account with few followers. Sam’s profile was rising more than ever from OpenAI’s success on GPT-3 and its most recent launch, GitHub Copilot. Instead, trolls attacked Annie, saying she wasn’t actually related to her brother.
Over the subsequent months, two reporters reached out to Annie, but she remained uncertain about how much to share with them. In September 2022, she resolved to speak openly. She tweeted again, naming Sam and Jack: “Sexual, physical, emotional, verbal, financial, and technological abuse. Never forgotten.”
Ten months later, in July 2023, after ChatGPT’s release and Sam’s rocket to global stardom, Annie received a message from New York’s Elizabeth Weil.
In the three months after the New York magazine article published, Annie’s OnlyFans income would jump up more than 10x, from around $150 a month to over $1,500. For a month during the board crisis, it would hit around $5,500. She stopped escorting, continuing only virtual sex work.
The family—or as Annie calls them, “her relatives”—have maintained that they have given her various forms of financial assistance throughout the years. Indeed, the support plan they agreed on after family therapy and the rent that Sam paid from mid-2021 to mid-2022 are examples. But for Annie, this money came too little too late, after she had already been desperate enough to turn to sex work. Other offers of support, including the house, generally had restrictions or conditions that she felt she could not accept.
In July 2023, Sam sent Annie one other message offering money without apparent conditions. A person had emailed both of them earlier that summer with the bugged-out energy of an internet sleuth, asking Annie to elaborate on her allegations. Annie responded to the three-way thread with a detailed account of how she had experienced her last few years. Sam was in the middle of his World Tour, ascendant. On June 5, the day he gave a well-received talk with Sutskever at Tel Aviv University in Israel, Annie was in his inbox, talking about the cruelty of her last few years in measured, eviscerating sentences.
He responded in rare uppercase on July 9, his World Tour officially over. “Sorry for taking so long to respond; it took me awhile to figure out what I wanted to say,” he wrote. “I don’t want any kind of ongoing relationship with you, and I respect that you don’t want one with me either. I am, however, happy to send you money and am hopeful that you can get through your health challenges.” He offered to restart their previous arrangement, the details of which he couldn’t quite remember, or to give her a lump sum payment. “For the record, I disagree with many claims in this email, but it seems pointless to try to engage,” he ended.
At that point, Annie no longer wanted Sam’s money. She simply wanted access to the money her father had left. She never responded to Sam’s email.
In addition to his 401(k), her dad had left behind a trust under her mother’s authority. In early 2024, with her additional income, Annie would retain her own lawyer and learn that her dad’s trust had been newly funded in 2023. As her story gained traction, the family would open up discussions through Gibstine’s lawyer over sending Annie monthly distributions from the trust with no strings attached. For the first time, Annie felt she had real negotiation leverage. The family said in their public statement that they expected to provide Annie monthly financial support “for the rest of her life.”
With the new distributions, Annie rented her first stable apartment in over four years. Soon after, she engaged another lawyer to prepare a child sexual abuse case against Sam to file it before her thirty-first birthday, on January 8, 2025. It would allege—and the family would vehemently deny—that Sam had sexually abused her beginning when she was around three and continuing until he was an adult and she was still a minor; it would seek damages in excess of $75,000. In October 2024, after another whirlwind of medical appointments, Annie would also finally receive a diagnosis for her underlying health condition: hypermobile Ehlers-Danlos Syndrome, the same genetic mobility disorder as Brockman’s wife.
In the lead-up to Annie’s story coming out in the New York magazine article, Sam began to tell people that his sister had borderline personality disorder. It was a private and sensitive matter, he told them. “He defanged her account before it even published,” one of those people says.
Borderline personality disorder is marked by severe challenges in emotional regulation and can lead to intense interpersonal relationships with extremes of idealization and fears of abandonment. Annie says she never received that diagnosis—nor did such a diagnosis appear in any of the therapy notes or medical records she shared with me. There is only one mark from her trauma therapist on Maui in August 2021 indicating that she was evaluating Annie for the disorder, which commonly arises after childhood sexual abuse. The therapist included a reference to a past history of sexual abuse but not the disorder in her final diagnostic impressions.
Two therapists I spoke to about borderline personality also underscored that the disorder usually goes away, either naturally or with the right treatment, which includes meditation and behavioral therapy that helps reaffirm a person’s self-worth, both tools that Annie has leaned into, but not psychotropic medication, as Gibstine encouraged and what the family’s statement appeared to refer to when saying Annie “refuses conventional treatment.” “The research is very positive on borderline personality disorder; it’s considered a good prognosis, diagnosis,” says Blaise Aguirre, an assistant professor of psychiatry at Harvard Medical School who has treated thousands of borderline patients but did not review Annie’s case specifically. “The vast majority of people will get better.”
In April 2024, Hannah Wong, who would soon be promoted to OpenAI’s chief communications officer, would also speak to me about Annie’s mental health. For six months, Wong’s team had said they were committed to arranging an office visit with me as well as interviews with key OpenAI leadership and employees as I repeatedly sought to engage them and hear their perspective. Five months in, they began to sour on the idea. Ten days before my flight to San Francisco, which I had already booked to visit the company’s headquarters, they notified me that they had reversed their decision: I would not be coming to the office, and they would no longer participate in my book.
Several days into my trip in San Francisco, which I took as planned, I told someone who personally knew Sam and Annie that I was speaking to her. The next day Wong texted me. “I hear you are in town?” she said, an odd formulation given why I had arranged my trip in the first place. We met at a Philz Coffee in Mission Bay, not far from a new office location that OpenAI was expanding into. After some meandering small talk and high-level discussions about my book, she directed the conversation to Annie.
“I don’t think I’m stepping out of turn here by saying Annie has mental health challenges,” Wong said. At this point, I had not yet reached out to OpenAI about Annie and had not brought her up in the conversation first. “Annie has good days and some really bad days,” she continued. “And the family is trying very hard to strike a balance between protecting her and not enabling her.” Here, she reiterated the point again for emphasis. “Notice that the family hasn’t put out any public statement denying what Annie said. It all comes back to protecting Annie.” She had also heard that some journalism programs had even discussed whether it had been ethical for Weil to include Annie in her profile. Maybe this, too, was something I should consider, she said.
It became clear that this was the main message Wong had reached out to me to deliver. Until then, she had not responded directly to my request to speak with her about the book and had only interfaced with me through a deputy. The importance she seemed to place on addressing Annie’s story highlighted the pressures that it was putting on Sam and the close link between the company and Sam’s personal matters.
Sam’s and Wong’s assertions about Annie’s mental health also struck me as another parallel between Annie’s experience and the experience of so many others sidelined or harmed by the empires of AI and their vision. Since resolving to tell her story, Annie has faced the same gulf of power that I have watched data workers and data center activists wrestle with. Her life has revolved around combing through and gathering as much documentation as possible to get anyone to listen to her. At times she has been consumed by a sinking feeling that no matter how much she speaks up, the world is somehow in a conspiracy against her. It’s the same loss of agency and anger I’ve seen etched on the faces of people globally when they throw so much of the little they have at challenging the empires’ narratives, and then watch as the people they are up against wield the kind of power that can deploy billions of dollars in capital, construct vast infrastructure, hire and fire tens of thousands of contractors, and, with a few soft-spoken words—at an event, to Congress, to heads of state, to journalists— smooth over the murmurs of protest in the way of their will.
In Annie’s case, after Weil’s profile, she was no longer shouting into a void. As her tweets began to go viral in October 2022, they came to the attention of someone important: Ilya Sutskever, right as he was grappling with his own complex feelings about Altman and what he viewed as Altman’s patterns of abuse.