Yahoo could have bought Google for $1M in 1998 — it passed, and passed again in 2002

Yahoo was the front page of the early internet — the most popular starting point for web users in the late 1990s. But its search was a human-edited directory, and as the web exploded it leaned on other companies to power actual search. In 1998, two Stanford students, Larry Page and Sergey Brin, approached Yahoo with an offer: they would sell their nascent search engine, Google, for $1 million. Yahoo declined.

Four years later, the mistake was visible. Google had become the best search engine on the web and was growing fast. In 2002, Yahoo's CEO Terry Semel opened negotiations to buy Google. Yahoo's final offer was about $3 billion; Google's leadership held out for around $5 billion, and no deal was struck. The failure to acquire Google that second time is widely considered one of the largest strategic errors in corporate history.

Yahoo went on to build its own search and to buy other companies, but it never caught Google, which grew into the dominant force in search and online advertising — and eventually a company worth more than a trillion dollars. Yahoo itself declined through the 2010s, cycling through CEOs, selling its core business to Verizon, and shrinking to a fraction of its former self. The two passed-on chances at Google remain the defining 'what if' of the internet era.