Apple Inc (NASDAQ:AAPL) is under pressure to go big in artificial intelligence, but history warns that mega-deals can quickly turn into mega-disasters.
From AT&T's (NYSE:T) costly Time Warner experiment to Microsoft Corp's (NASDAQ:MSFT) failed Nokia buyout, corporate America is littered with deals that once looked bold but ended in regret. Now, with Apple Senior Vice President of Services Eddy Cue reportedly floating ideas of acquiring AI firms such as Mistral or Perplexity, the question is whether CEO Tim Cook should risk repeating those mistakes.
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When Big Bets Backfire
AT&T's $85 billion takeover of Time Warner ended in a humiliating unwind just four years later, costing shareholders billions. Microsoft's approximately $7 billion Nokia acquisition was another costly lesson in how ambition can cloud judgment. Both stand as reminders that the price of going big often outweighs the payoff. For Apple, buying an AI startup at inflated valuations could be déjà vu.
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The Exceptions That Prove The Rule
Of course, not all acquisitions go south. Alphabet Inc‘s Google's $1.65 billion YouTube purchase and Meta Platforms Inc.'s (NASDAQ:META) about $1 billion Instagram bet turned into defining wins. Even Apple's approximately $278 million buy of Palo Alto Semiconductor laid the foundation for its breakthrough in custom chip design.
But crucially, these were smaller, earlier-stage acquisitions — not headline-grabbing mega-deals.
Cook's Discipline May Be Apple's Edge
Tim Cook's decision to pass on Netflix Inc (NASDAQ:NFLX) and Tesla Inc (NASDAQ:TSLA) may have looked conservative, but restraint has served Apple well. By avoiding overpriced bets, Apple has maintained enviable margins and firepower for strategic partnerships — such as its integration of ChatGPT into the iPhone.
Shareholders may find that Apple's best move in AI is simply not overplaying its hand.
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