A year ago, OpenAI seemed to have an untouchable lead in the AI ​​race.

It was by far the dominant AI platform for consumers. Competitors like Meta were struggling (and spending millions of dollars on new hires) to catch up. Sam Altman had enough money and influence to hire famed Apple designer Jony Ive to build him a mysterious device meant to fit the iPhone I helped build.

Now the narrative has changed: OpenAI is struggling to catch up with rival Anthropic, which had focused on enterprise accounts rather than selling to individuals. Altman appears to be constantly reorganizing his leadership structure and then reorganizing it again. And Apple is suing OpenAI, alleging that Altman’s company stole its employees and stole its secrets.

It’s an open question whether OpenAI was wrong to focus on consumers rather than businesses from the start. Or if you have the right executives in the right roles. You need time to see how all that plays out. (I asked OpenAI if they wanted to weigh in on any of this.)

But now we can focus on Apple’s lawsuit. Because what’s interesting to me isn’t just the spectacle of one of the most powerful companies in the world suing one of the most valuable startups in the world (and possibly dragging its legendary former employee to court as well, although I haven’t been named in the lawsuit).

This is the second time OpenAI has aligned itself with a leading tech giant and ended in a messy breakup.

That first break was with Microsoft, which at one time seemed to be OpenAI’s most important big tech ally. Microsoft first invested $1 billion in OpenAI back in 2019, and then made a much larger commitment in 2023, months after OpenAI ushered in a new era of AI with ChatGPT. When Altman was temporarily fired by his board of directors later that year, Microsoft CEO Satya Nadella provided crucial support to Altman in his negotiations to regain his job.

But by April of this year, Microsoft and OpenAI had more or less parted ways. They still have a deal, but the exclusive relationship they had forged a few years earlier is now formally non-exclusive. Of note: That deal came weeks after a report that Microsoft was considering suing OpenAI for allegedly violating its existing contract.

The Apple/OpenAI story is not a carbon copy of the Microsoft/OpenAI story, but it rhymes.

In 2024, Apple blessed OpenAI’s status as the dominant AI company by giving it pole position on the iPhone: Apple was not forcing its users to use ChatGPT, but was going to integrate the chatbot into its phone software. It seemed like a victory for both companies.

OpenAI then bought Ive’s company for $6.5 billion and announced plans to build a mystery device that isn’t supposed to be an iPhone, but is also clearly intended to compete with the iPhone in some way. And in May of this year, OpenAI executives were so disappointed with their partnership with Apple that they were reportedly considering suing Tim Cook’s company for breach of contract.

Instead, Apple is suing OpenAI.

I don’t have an opinion on the merits of Apple’s case. So far, we only have the (preliminary) version of the Apple story. And there are many observers, including my colleague Alistair Barr, who are not particularly fond of Apple.

It’s also not the first time Apple has used the court system to fight a potential iPhone rival: While it didn’t sue Google directly, in 2011 it did sue Samsung, which was using Google’s Android software to build an iPhone rival.

But I think it’s notable that OpenAI has established two very important alliances with Big Tech giants, and both ended in acrimony.

An all-seeing perspective would be to argue that fighting with big tech companies is a sign that you may be a big tech company yourself. And that all these guys have enormous resources, and that lawsuits take forever to resolve, and when they do, the world may have changed so radically that the initial fight becomes pointless. We’re all adults here, let’s move on.

But if you’re a big tech executive working with, or considering, OpenAI, you may already have concerns about the company’s leadership. This week’s news may give you even more reason to worry.