Apple's AI plans took another hit on September 13, 2025, with Reuters reporting that Robby Walker, senior director of the company's Answers, Information, and Knowledge team, will leave the company next month. Walker's departure marks the latest in a series of high-profile AI executive exits that underscore Apple's struggle to compete with Google, OpenAI, and Microsoft in AI development.
A Pattern of Executive Flight
Walker's exit is part of a bigger problem - Apple can't keep AI talent around. MacRumors reported in July 2025 that other high-level AI employees had already departed for Meta, suggesting systematic issues within Apple's AI organization. Walker, who had previously overseen Siri development before transitioning to AI-focused roles earlier in 2025, represents a significant loss of institutional knowledge and leadership.
The timing is particularly concerning for Apple. Robby Walker lasted what, 6 months in the AI role? That's not normal executive turnover - that's a sinking ship. His departure comes as Apple faces mounting pressure to deliver meaningful AI capabilities that can compete with Google's Gemini Live and other advanced chatbot systems.
Apple Intelligence Delays Mount
Walker's exit coincides with continued delays in Apple's Apple Intelligence suite, the company's flagship AI initiative announced with considerable fanfare in 2024. Most notably, Apple's long-awaited AI-powered Siri upgrade has been reportedly delayed into 2026. The 2026 Siri upgrade delay is corporate speak for 'we have no fucking clue how to compete.'
The contrast with competitors is stark. Google's Gemini Live offers naturalistic conversation capabilities that Apple's current Siri iteration cannot match. Amazon's Alexa continues to dominate smart home AI interactions, and Microsoft's Copilot integration across Office applications provides practical AI utility that Apple's ecosystem lacks.
Apple's getting crushed in enterprise AI too. Their business offerings are embarrassingly limited compared to Microsoft's AI integration across Office, or Google's cloud AI services that actually power real business apps. Apple's developer tools for AI integration lag behind Google's TensorFlow and Microsoft's Azure AI.
Strategic Implications
When your AI director bails after 6 months, something's seriously fucked. Apple's usually good at the slow, methodical approach, but AI might need the rapid-fire iteration that Google and OpenAI do.
Apple's obsession with privacy means their AI runs on your phone instead of powerful cloud servers - which is why it sucks compared to everything else. The privacy-focused approach sounds great until you realize it means 'slower and dumber than everyone else.'
Siri still can't handle "Set a timer for 3 minutes and 30 seconds" without fucking it up - it either sets a 3-minute timer or gets confused and asks "Did you mean 30 seconds?" Meanwhile Google's Gemini Live actually understands context and nuance like a human would.
iOS 18.1 beta has widespread memory crashes affecting AI apps. Developer forums show third-party AI apps crashing with EXC_RESOURCE_MEMORY errors. Stack Overflow threads document Core ML framework memory leaks with models over 2GB, with MLMultiArray objects not getting deallocated properly. Apple's documentation doesn't mention these limits.
Every AI exec that leaves takes tribal knowledge with them. Apple's basically starting over each time someone bolts for Meta or Google. That's not normal executive turnover - that's a sinking ship.
Apple's Stock Doesn't Give a Shit
Apple's stock is fine because people still buy iPhones regardless of how broken Siri is. But eventually, users are going to notice their phone is dumber than everyone else's.
The scary part? Apple's ecosystem only works if everything talks to everything else. When Google Assistant works better on an iPhone than Siri does, that's a fundamental problem. Users increasingly install Google Assistant to get reliable voice commands - Apple's integrated ecosystem advantage falls apart when the AI connecting everything is broken.
Apple's community forums are full of complaints about Siri failing to recognize connected smart bulbs. Users report Siri responding "I can't find any lights" while standing in rooms with 6+ connected devices. These failures force manual control through the Home app, while Alexa handles identical requests instantly. The reliability gap is pushing users toward Amazon's ecosystem.