Let me start by stating the obvious. If we were to sign CC and he stays healthy for five full years, he is undoubtedly worth the money. However, at what point are the Brewers risking too much of their payroll to try to sign him? To be honest, I'm personally not sure whether 5 years/$100 million is too much or not. I do know that this contract would be tying up somewhere between 20 and 25 percent of the Brewers payroll for the next five years and signing starting pitchers to long term deals is just about the riskiest thing a team can do.
If he pitches like he did last year, then yes, he is worth it. Keep in mind though, the Rockies were saying the same thing when they signed Mike Hampton. Hampton then proceeded to struggle for two years with the Rockies, pitch two average years with the Braves, and then pitch a whopping 15 games and 147 innings in the next four years. It should also be worth noting that before this big contract, Hampton had pitched three more sub-4 ERA seasons and fewer total innings than CC currently has pitched. Similar things can be said about the big contracts and lack of production from Carl Pavano and Barry Zito.
All in all, I think we have to seriously consider what we wish for with CC. As much as we would love to have him back as a Brewer, we must be sure to envision him both as a Cy Young Award winner as well as the next Mike Hampton when we are thinking about the contract situation.