Apple: Cupertino convulsions continue with two new departures

At this point, Apple’s org chart is starting to look like a snow globe someone shook too hard. The company has already lost its AI chief John Giannandrea and veteran design executive Alan Dye.

Now two more long-timers are stepping out of frame, adding fresh turbulence to a leadership team that is supposed to be steering the company through its most embarrassing strategic gap in years: falling behind in AI.

Kate Adams, Apple’s general counsel since 2017, is retiring late next year. Lisa Jackson, the vice president for Environment, Policy, and Social Initiatives, will leave in January.

Jackson was one of Apple’s most recognisable leaders outside its core product organisation, a former EPA head who spent more than a decade binding the company’s green ambitions to its corporate identity.

Her role became trickier under the Trump administration, which treated corporate climate initiatives as optional at best and political liabilities at worst.

Adams, meanwhile, helped Apple weather antitrust scrutiny in the US and Europe. Much of that centred on Apple’s app store policies, which have slowly degraded from business model to geopolitical lightning rod. Her exit comes at a moment when global regulators are paying even closer attention, not less.

Apple has named Jennifer Newstead as its incoming general counsel. Newstead is a legal heavyweight with a CV that reads like a government Rolodex. She arrives from Meta, where she served as chief legal officer, and before that held positions across the US State Department, the Office of Management and Budget, the Department of Justice and the White House.

She will report directly to Tim Cook. It is a strong hire on paper. Whether it signals a defensive crouch or an ambition to reassert control over Apple’s regulatory narrative is an open question.

Cook framed the transition as business as usual. Of course he did. But the context betrays the spin. Apple is losing senior leadership at the exact moment its internal confidence is wobbling. Designers have publicly and privately criticised the company’s slipping attention to detail.

AI teams have been bleeding talent to Meta, which has been scooping up disaffected Apple engineers with the hunger of a rival that thinks it can finally win something. Apple also pushed back the launch of its AI powered Siri overhaul, which will now run Google’s models behind the scenes.

That is not a footnote. That is an admission that Apple Silicon and Apple AI are not yet ready for a world where your phone is supposed to think instead of politely waiting for commands.

The departures also sit atop a longer list of changes. Chief operating officer Jeff Williams announced his retirement in July, handing responsibilities to Sabih Khan. Giannandrea’s former Siri team now reports to Mike Rockwell, who previously led the Vision Products Group.

Apple’s AI driven search lead, Ke Yang, decamped to Meta. Ruoming Pang, who ran AI models at Apple, also left for Meta earlier this year. One or two departures can be dismissed as churn. This is not churn. This is a slow tectonic slide.

It is possible Apple sees this as a chance to reset its leadership for the AI era. It is also possible the reset has already happened and the company is only now absorbing the consequences.

Either way, the world’s most valuable hardware brand is entering 2026 with a leadership roster that looks increasingly like a patchwork of new hires, departing legends and mid-flight reorganisations.

The iPhone maker used to insist that its internal stability was one of its greatest competitive edges. The past few months have been a reminder that even Apple can wobble.

The question is whether this is pruning or decay. We will not know until we see the next generation of AI devices that Apple has been promising for years and delaying for just as long.