Well, that's the dilemma, isn't it? If he was willing to take 4/$100M, he'd already be signed. Probably not by the Twins, because 25-29 other front offices would likely take him at that price, and he'd get his pick of teams. Every team can make this same calculation and pull the trigger, if he'd accept. Yes, a longer contract for more money than this will almost surely be dead money. Why do I not care? In effect an overpay in free agency is the Failure Penalty* for not having developed a difference-maker at a given position. In the case of front-line starting pitchers, Berrios is still a Maybe, and only ESan really qualifies; you need more than one. We're in this position because Terry Ryan, a good baseball man, didn't deliver in this area. He did apparently deliver profits each and every year, even when the team was bad. To me, that is a false profit (pun intended, I guess). Pro sports aren't like the average business, and to me there should be no presumption that profits are guaranteed through thick and thin. Ownership needs to recognize that the cash they tucked away 2012-14, an era when paying more than they did for new players probably would indeed have been a waste, isn't really theirs to keep. I realize that "ashburynobody" presuming to tell billionaires how to spend their money carries no weight with them. And I'm not saying they should keep shelling out money for free agents without limit. All I'm saying is, by my bookkeeping, they are currently in arrears, and they aren't admitting it. Almost certainly, a deal for 3 years or more receives scrutiny from this (or any) ownership. That's assuming they are happy with the top guys in the front office; they won't be firing them for a couple of years, so they set a budget and then let their guys work within it, for 1- and 2-year deals. But a deal for many years may be an albatross for a future GM, if they need to fire the current one, and they won't be able to hire a good one with that albatross, so ownership has to be prepared to eat a bad contract and let the new GM start with a relatively clean slate, if they sign off on it. This is the moment when ownership needs to step up and make that commitment to taking on potentially dead money later on, in the interest of getting the best starting pitcher available. * Actually I would call it the Stupidity Tax, if a GM has a self-deprecating sense of humor and recognizes that everyone finds themselves in the unfortunate situation from time to time.