Here's my counter-argument to a portion of that. Let's say that the Cubs awarded Ramirez a 6/$90m deal. He'll be 28/29 next season. Let's say he takes a Lowell-like career path and he goes into a massive slump when after turning 31. That gives the team between 2 1/2-3 years of production before he goes into the crapper, so he'd have something like 3/$45m on his contract. As we've seen with countless players, from Lowell to Griffey to plenty of other hitters, teams will always be willing to trade for these guys. Teams talk themselves into thinking a player will eventually turn it around all the time. If Ramirez goes into a slump like that, I'm sure some other team would be fine with trading for him (be it by himself or as a part of a package). The Cubs would have to pick up a portion of his salary, but so what? This team wastes money all the time and is a big market team. Part of the advantage of being a big market team is that you can absorb these kinds of contracts be it through toughing them out or paying a portion of them to drop the guy on some one else.