Stephen Grocer has a great post about Yahoo’s M&A track record: the companies it did buy and shouldn’t have, as well as the companies it didn’t buy and should have.
In the former camp: the $3 billion acquisition of GeoCities, the $4.3 billion acquisition of Broadcast.com. In the latter camp, Yahoo could have bought, but passed on, MySpace, Facebook, YouTube, and even, at one point, Google.
Of course, Yahoo being Yahoo, all of those companies, even Google, might have turned into GeoCities of their own had they been incorporated into the maw of the original Web Portal. Even Google’s not all that great at acquisitions: look at how Dodgeball went nowhere after Google bought it.
In fact, with the possible exception of MySpace, it’s hard to think of any big tech-space acquisition which looks like genius in hindsight. YouTube might do eventually, but the jury’s still out on that one. If Microsoft does end up buying Yahoo, it’s going to have to buck a pretty strong trend.