re: 24 wins & 23 losses after Drew signs his $100 million deal.

Moneywise the deal we made with Drew is not terrible. Its pretty much in line with what any team who thinks they have a SB capable QB. Not every team thinks they do, so they dont pay him like that. Maybe thats a better strategy, but we couldnt keep Drew in that strategy.
If youve noticed, some of his peers and arguably inferior Qbs have beaten him in contract numbers. Noticeably Romo, Flacco, Rodgers, I think Roethlisberger.
Its called the "Lake Woebegone Effect" and if you can understand it, you'll understand that we're not crazy for giving Drew all that money.
The effect is this. You give a dude the best money, because you think he can get the best results. You dont give a dude less than the best cuz thats not what hes there for.
Over the years the price for these guys gets higher and higher until the stigma of QB=Results goes away.
And thats a whole nother discussion which I think a lot of people are tryna make legitimate points about.