Maybe I remember it wrong but even in 2008 I felt that there was at that point some question of what ... Yahoo was / would be.
IIRC Yahoo at that point was a big name that wasn't irrelevant, but whatever they would be in the future seemed like it would have be be akin to creating new product(s) / company / sea change type move.
It was hard to imagine them becoming worth 66% more anytime near that time (even without hindsight).
Microsoft was try to buy market share in the search engine. This is when they were making a play for Bing to be a market contender in Search. We don’t know what would have happened if Bing had 20% market share out the gate, as well as access to Yahoo expertise/tech. A significant share of Search today would be worth significantly l more than $44B, and this deal would have been a fair gambit for Microsoft to make.
It was a very good offer, but it wasn’t enough for Yahoo to sell. Perhaps a larger offer would have helped, but I think Yahoo had an inflated opinion of their own worth.
IIRC Yahoo at that point was a big name that wasn't irrelevant, but whatever they would be in the future seemed like it would have be be akin to creating new product(s) / company / sea change type move.
It was hard to imagine them becoming worth 66% more anytime near that time (even without hindsight).