Tim Cook’s nearly 15-year tenure as Apple CEO is entering what could be its most critical phase, as the 65-year-old executive confronts mounting pressure to solidify Apple’s position in the artificial intelligence race. With retirement speculation swirling and 2026 shaping up as a pivotal year, Cook faces the dual challenge of delivering a long-delayed Siri update while navigating an increasingly competitive AI landscape where Apple appears to have fallen behind rivals like Google, Microsoft, and Meta.
Since taking over from Steve Jobs in 2011, Cook has transformed Apple into a $4 trillion company (reached in October 2025), expanding beyond the iPhone cash cow to build a comprehensive ecosystem including Apple TV+, Apple Fitness+, Apple Music, and the Apple Watch. According to Morningstar analyst William Kerwin, Cook’s greatest accomplishments include “the financial evolution of the company, the integration of Apple silicon, and maintaining the iPhone’s dominant walled garden ecosystem.”
However, Apple Intelligence—the company’s AI platform—has struggled to gain traction, failing to deliver the iPhone upgrade super cycle that analysts like Wedbush Securities’ Dan Ives predicted. The iPhone 16 family underperformed expectations, though Cook expressed optimism that the iPhone 17 lineup would drive growth, particularly in China where revenue declined 4% in the most recent quarter. The company also lost several AI researchers to competitors like Meta in 2025, raising concerns about talent retention.
Forrester analyst Dipanjan Chatterjee notes that while Cook has maintained steady growth, “he has not overseen a step-change innovation that resets Apple’s competitive position for the next two decades, as Jobs did with the iPhone.” The Vision Pro headset, launched in February 2024 at $3,500, failed to achieve mass adoption, and the long-rumored Apple Car project appears to be scrapped.
Martha Heller, CEO of specialized technology executive search firm Heller, argues that AI has redefined what legacy means for CEOs. “Cook has laid the foundation for Apple’s AI future, but the next 12 to 18 months will determine whether reinvention becomes his defining legacy,” she stated. A revamped Siri is expected in 2026, and supply chain analysts predict a foldable iPhone could arrive as early as fall 2026, aligning with Apple’s “not first, but best” strategy.
Succession planning has also intensified, with the Financial Times reporting Cook has accelerated his search for a replacement. John Ternus, senior vice president of hardware engineering, has been identified by Bloomberg as the most likely successor, following the retirement of longtime No. 2 Jeff Williams and the planned spring 2026 departure of AI chief John Giannandrea.
Key Quotes
AI has redefined what legacy means. Ten years ago, the goal was to leave a solid foundation so the next leader could create change intentionally without chaos. Now, it’s up to leaders to create an AI road map — from the nitty-gritty of products to the mindset of the board — to take a company into the future.
Martha Heller, CEO of Heller executive search firm, explains how AI has fundamentally changed the expectations for CEO legacies, putting pressure on Cook to demonstrate not just operational excellence but technological vision for Apple’s AI future.
Cook has laid the foundation for Apple’s AI future, but the next 12 to 18 months will determine whether reinvention becomes his defining legacy.
Heller’s assessment highlights the critical window Cook faces to prove Apple can compete in AI, suggesting his entire tenure may ultimately be judged by how successfully he positions the company for the AI era.
While Cook has kept Apple’s growth trajectory moving forward at a steady clip, he has not overseen a step-change innovation that resets Apple’s competitive position for the next two decades, as Jobs did with the iPhone.
Forrester analyst Dipanjan Chatterjee draws a stark contrast between Cook’s incremental approach and Jobs’ revolutionary impact, suggesting Apple needs a breakthrough AI innovation to maintain its competitive edge.
Tim Cook’s greatest accomplishments are the financial evolution of the company, the integration of Apple silicon, and maintaining the iPhone’s dominant walled garden ecosystem.
Morningstar analyst William Kerwin summarizes Cook’s legacy to date, acknowledging his operational and financial success while implicitly noting the absence of transformative product innovation in the AI category.
Our Take
Cook’s predicament illustrates a fundamental tension in the AI era: can operational excellence substitute for technological first-mover advantage? Apple’s historically successful strategy of perfecting rather than pioneering may not translate to AI, where network effects and data advantages compound rapidly. The company’s talent losses to Meta and other rivals suggest internal recognition that Apple may be falling behind. What’s particularly striking is how AI has become the lens through which Cook’s entire legacy is now being evaluated—despite building a $4 trillion company, his tenure risks being defined by whether Apple becomes an AI leader or follower. The upcoming Siri overhaul and potential foldable iPhone represent high-stakes bets that could either validate Cook’s patient approach or confirm fears that Apple has lost its innovative edge. The succession question adds urgency: whoever replaces Cook will inherit these AI challenges at a moment when catching up may be exponentially harder.
Why This Matters
This story represents a critical inflection point for one of the world’s most valuable technology companies as it navigates the AI revolution. Apple’s struggle to establish itself as an AI leader—despite its massive resources and brand loyalty—illustrates how rapidly the competitive landscape has shifted. The company’s more conservative approach to AI investment contrasts sharply with the billions being poured into AI by Microsoft, Google, and Meta, raising questions about whether Apple’s traditional “not first, but best” strategy will succeed in an era demanding rapid innovation.
The implications extend beyond Apple itself. If the world’s most profitable smartphone maker cannot successfully integrate AI into its products, it signals potential challenges for the entire consumer technology industry in monetizing AI capabilities. Cook’s succession planning also matters enormously—the next CEO will inherit both Apple’s strengths and its AI challenges at a moment when technical expertise may be more critical than operational excellence. The outcome will influence how hundreds of millions of consumers experience AI technology daily and whether Apple can maintain its premium market position in an AI-driven future.
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Source: https://www.businessinsider.com/apple-2026-could-be-pivotal-shape-ceo-tim-cook-legacy-2026-1