The ink is still wet on Verizon Communications Inc.‘s (NYSE:VZ) new deal to acquire Yahoo! Inc. (NASDAQ:YHOO) for $4.8 billion. Unfortunately, it will probably be several years before VZ investors can tell whether or not $4.8 billion was a good price.

Huge buyouts like this one are always a big risk, but the tech sector in particular has a storied history of terrible deals and mind-boggling missed M&A opportunities. In fact, YHOO has been involved in more than its fair share.

Here’s a look at 5 of the biggest M&A blunders in the history of tech.

Yahoo Rejected $44.6 Billion Bid by Microsoft (2008)

This is about as simple of a math inequality as you can find:

$44.6 billion > $4.8 billion

That’s all it takes to see just how much of an opportunity YHOO management missed back in 2008 when the company rejected an offer from Microsoft Corporation(NASDAQ:MSFT) because co-founder Jerry Yang felt it was too low. Eight years later, YHOO sold for a little more than one-tenth that amount.

Yahoo Passed on Buying Google for $1 Million (1998)

I really hate to pick on YHOO, but it’s…

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