Hall of Shame

Yahoo Said Microsoft's $44.6 Billion Offer "Massively Undervalues" Them. They Sold for $4.8 Billion.

Posted February 09, 2026

"Microsoft's offer massively undervalues Yahoo."

— Yahoo Board of Directors, official response to Microsoft

February 2008

What Actually Happened

In February 2008, Microsoft came knocking with a $44.6 billion offer to acquire Yahoo — a 62% premium over the stock price. Yahoo's board, led by co-founder Jerry Yang, did what any self-respecting tech company would do: they said no thanks, you're lowballing us. "Massively undervalues" were the exact words they leaked to the Wall Street Journal. They wanted at least $40 per share instead of Microsoft's $31. Microsoft eventually walked away. Yahoo's stock proceeded to crater. The company spent the next decade slowly bleeding relevance while Google ate their lunch, breakfast, and dinner. In 2016, the once-mighty Yahoo finally sold its core internet business to Verizon for $4.83 billion — roughly 10% of what Microsoft offered. Jerry Yang resigned shortly after the Microsoft debacle. The board members who rejected the deal presumably went on to write books about "knowing your worth" in negotiations.

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