Silicon Valley loves a blockbuster deal, but some of its best stories come from the ones that slip away. Windsurf was hours from a three‑billion‑dollar sale to OpenAI when Microsoft’s GitHub Copilot clauses threatened to scoop up its tech. The talks froze, Google pounced with a two‑point‑four‑billion “reverse acquihire,” Cognition grabbed the rest, and a company doubling revenue every few months was split in just three days.

A decade earlier Tesla nearly vanished into Google. In 2013, with cash burning fast, Elon Musk asked Larry Page to buy the automaker for six billion dollars plus five in guarantees. Model S sales spiked at the last minute, Musk tore up the term sheet, and Tesla drove off on its own.

Microsoft’s forty‑four‑billion bid for Yahoo in 2008 ended the same way. Steve Ballmer sweetened his offer, Jerry Yang wanted more, and a side flirtation with Google sealed the breakup. Microsoft walked, Yahoo drifted, and Bing learned to fight solo.

In 2009 Steve Jobs called Dropbox a mere feature, offered a nine‑figure exit, and was politely shown the door. Dropbox stayed independent, iCloud arrived later, and “Dropbox me” became common slang.

Today regulators can kill a romance faster than ego. Adobe and Figma spent fifteen months courting before scrapping their twenty‑billion merger when Europe and the UK signaled a veto. The companies issued a brisk joint statement and returned to competing.