As I write this, Apple’s 2026 Worldwide Developers Conference (WWDC) kicks off tomorrow, and the unveiling of a feature-rich new version of Apple’s AI assistant Siri is rumored to play a big role in kicking off WWDC.
But apparently, Siri’s recent history has been as complicated behind the scenes as it has been in public, and if this version of Siri is a success, it seems that the man largely responsible—at least according to Bloomberg reporting—she won’t be receiving her flowers.
His name is Mike Rockwell, and in a unusually gossipy edition of your Power On newsletterBloomberg’s Mark Gurman describes the 2025 meeting that put Rockwell in the driver’s seat of the new Siri. This was after Apple Intelligence failed to make a big splash and, in Gurman’s thinking, satisfy the world that Apple was sufficiently equipped with AI.
The anonymously sourced newsletter says that Rockwell signaled around 2016 that AI was going to be big and recommended that the company take significant steps to prepare, but not much came of it and he was then put in charge of Apple Vision Pro. While it wasn’t exactly a runaway success, Vision Pro was an impressive achievement that gave Rockwell credibility among an assembly of executives who met to come up with an AI game plan to deliver to CEO Tim Cook, who wasn’t there that day.
Apple’s then-head of artificial intelligence, John Giannandrea, was in the room. And it seems that Rockwell, for lack of a better term, harassed Giannandrea completely and absolutely. Gurman says Apple software chief Craig Federighi “led much of the discussion, but Rockwell emerged as a powerful voice.” Apparently, Rockwell thought he was going to get a promotion to a senior vice president position like Giannandrea, but that wasn’t the case. You just received the Siri-centric aspects of Giannandrea’s tasks, according to Gurman’s report from last year. Giannandrea’s retirement from Apple It was announced nine months later.
In April of this year, Gurman wrote that Apple’s incoming CEO John Ternus is a long-time opponent of the Vision Pro (Rockwell’s baby) and that Ternus has essentially killed that entire product categoryleaving Rockwell “weighing his future.”
And at WWDC, Gurman says Rockwell won’t take the stage and show off the new Siri. Gurman predicts that current CEO Tim Cook will introduce Federighi, who in turn will introduce the new AI assistant without Rockwell’s involvement, and there will be presentations from other Apple employees whom Gurman refers to as “Federighi’s lieutenants.”
Rumors about the features Rockwell has brought to the new Siri are extensive and quite consistent. The assistant is expected to be aware of the context extracted from your personal information and documents, as well as what is on your screen. It will also reportedly have a dedicated chatbot feature and a new look. It has been More or less confirmed by Apple. that this is all powered by an LLM essentially rented from Google—a deal Gurman says was struck by Mike Rockwell himself.
Is Rockwell preparing to slip away, misunderstood and hated? like batman at the end of the dark knight? Let’s not go crazy. This is anonymously sourced tech business journalism. There are no superheroes here. But the story could make an interesting comic anyway.
