Jeff Williams, Apple's Chief Operating Officer and right-hand executive to CEO Tim Cook, has announced his retirement after 27 years with the company. This departure comes amid challenges Apple faces in advancing its artificial intelligence (AI) strategy and ongoing speculation about the company's leadership succession. Analysts and industry observers are debating whether Tim Cook, who lacks a product development background, should continue as CEO or be succeeded by a new leader who can better steer Apple's AI ambitions. Some experts suggest that while Cook is a skilled logistics expert, a fresh perspective is needed to address the company's recent missteps, including issues with the Vision Pro product. Despite these concerns, others believe Cook remains the appropriate leader to guide Apple through its AI transition before eventually passing the baton to a successor, potentially Apple executive John Ternus. The COO's exit also raises questions about the future leadership of the Apple Watch division. Overall, Apple's succession plans have become a focal point as investor frustration grows over the company's AI progress and strategic direction.