#4
Yahoo-Tumblr ($1.1B, 2013)
Yahoo's $1.1 billion acquisition of Tumblr in 2013 suffered a 99.7% loss when it sold to Automattic for under $3 million. The deal imploded after Yahoo killed Tumblr's NSFW content, which drove a third of its engagement, slashing user traffic by 50%. Marissa Mayer's strategic misstep remains a textbook example of destroying platform value through content moderation.
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