As I write this, Apple’s 2026 Worldwide Developers Conference (WWDC) kicks off tomorrow, and rumor has it the unveiling of a feature-rich new version of Apple’s AI assistant, Siri, will play a major role in WWDC’s kickoff.
But apparently, the recent history of Siri has been as messy behind the scenes as it has been in public, and if this version of Siri is a success, it sounds like the guy largely responsible—at least according to Bloomberg’s reporting—isn’t getting his flowers.
His name is Mike Rockwell, and in an unusually gossipy edition of his Power On newsletter, Bloomberg’s Mark Gurman describes the 2025 meeting that placed Rockwell in the driver’s seat of new Siri. This was after Apple Intelligence failed to make a big splash, and—Gurman’s thinking goes—satisfy the world that Apple was sufficiently AI-pilled.
The anonymously sourced newsletter says Rockwell signaled in about 2016 that AI was going to be important, and recommended that the company take major steps to prepare, but nothing much came of that, and he was later put in charge of the Apple Vision Pro. While not exactly a smashing success, the Vision Pro was an impressive achievement that gave Rockwell credibility among an assembly of executives who gathered to figure out an AI game plan to hand over to CEO Tim Cook, who wasn’t there that day.
Apple’s at-the-time AI chief John Giannandrea was in the room. And it sounds like Rockwell, for lack of a better term, mogged Giannandrea completely and utterly. Gurman says Apple’s head of software Craig Federighi “led much of the discussion, but Rockwell emerged as a powerful voice.” Apparently, Rockwell thought he was getting a promotion to a senior VP position like Giannandrea’s, but he wasn’t. He just received the Siri-centric aspects of Giannandrea’s duties, according to Gurman’s reporting from last year. Giannandrea’s retirement from Apple was announced nine months later.
In April of this year, Gurman wrote that incoming Apple CEO John Ternus is a longtime opponent of the Vision Pro—Rockwell’s baby—and that Ternus has essentially killed that whole product category, leaving Rockwell “weighing his future.”
And at WWDC, Gurman says Rockwell won’t take the stage and show off new Siri. Gurman predicts that current CEO Tim Cook will introduce Federighi, who will in turn introduce the new AI assistant without Rockwell’s input, and there will be presentations from other Apple employees referred to by Gurman as “Federighi lieutenants.”
The rumors about the features Rockwell has brought to new Siri are extensive and pretty consistent. The assistant is expected to be aware of context drawn from your personal information and documents, as well as what’s on your screen. It will also reportedly have a dedicated chatbot function, and a new look. It’s been more or less confirmed by Apple that this is all powered by an LLM essentially leased from Google—a deal that Gurman says was brought about by Mike Rockwell himself.
Is Rockwell preparing to slink away, misunderstood and hated like Batman at the end of the Dark Knight? Let’s not go crazy. This is anonymously-sourced tech biz journalism. There are no superheroes here. But the story might make an interesting comic book anyway.
Read the full article here
