If you’ve watched Tim Cook lead Apple over the past decade, it’s hard to imagine his legacy being questioned. Since taking over from Steve Jobs in 2011, Cook has delivered record-breaking results, turned Apple into the world’s most valuable company, and created more shareholder value than Jobs ever did. But now, in a rapidly shifting tech landscape led by artificial intelligence (AI), the confidence that once surrounded his leadership is beginning to waver.
You’re not alone if you’ve sensed something is off. Apple is seeing key figures leave, just as AI reshapes the future of technology. In the latest shake-up, Apple announced that Chief Operating Officer Jeff Williams will retire by the end of the year, marking the end of a 27-year tenure with the company. That news came just one day after the company’s top AI executive, Ruoming Pang, exited to join Meta. Not long before, senior AI researcher Tom Gunter also left Apple. These departures have painted a picture of a quiet exodus at a crucial moment.
AI competition heats up while Apple lags behind
On the broader market, Apple’s stock performance is not encouraging. Over the past 12 months, Apple shares have dropped by 7.2%. In comparison, the S&P 500 has risen 6.5%, and the Nasdaq has surged 12.9%. For investors like you, these numbers send a worrying signal. Tech rivals are charging forward in the AI race, while Apple appears to be falling behind.
One name that keeps surfacing in the conversation is Jonathan Ive, also known as Jony Ive. Apple’s former design genius, who left the company in 2019, is now working closely with OpenAI. There’s intense speculation that he’s developing a new AI device—possibly a pendant or a pen—that could redefine the way we interact with technology. And while the rumour mill churns, Apple has kept quiet. If the company has similar innovations in the works, it’s keeping them well out of sight.
When it comes to existing AI-related products, Apple’s line-up feels limited. The Vision Pro mixed-reality headset is innovative, but it is aimed at a niche market. Meanwhile, the HomePod and HomePod mini smart speakers have seen only moderate success. With smartphones still at the heart of Apple’s business, the big question is: what happens if smartphones stop being the centre of people’s digital lives in the AI age?
As MoffettNathanson analyst Michael Moffett puts it, “There is this nagging question among investors… that Apple is unprepared for something transformational.”
The next chapter could define Cook’s legacy
You might be wondering whether Tim Cook still has a bold move left. It’s possible. Apple is famously secretive, so a surprise announcement—a new product, a landmark partnership, or even the acquisition of a major AI company—could change everything in an instant. If Cook can steer Apple into the AI era with the same sharp strategy that led to its dominance in smartphones, he might yet secure his place as one of the most outstanding CEOs in tech history.
But if such a moment doesn’t arrive soon, the pressure on Cook will likely grow. The board of directors—and shareholders like you—will have to consider whether Cook is still the best person to lead Apple into this new technological age. The world of AI isn’t just a new feature or product line; it’s a fundamental shift in the way we think and operate. And it’s a shift that might require new leadership for Apple to stay at the top.
