This is EXACTLY the question. Let's say we go out and get Ellsbury, Santana, and Jemenz. Ellsbury could be injury prone or simply play at a substandard level from day 1 (see Hamilton/Upton/Bourn) and have a negligible WAR the last couple years of their contracts. Jemenez could easily regress to the 5+ ERA pitcher he was in 2012 and Santana could do the same, especially as they age. Now you have over $80M/year in 2017-18 (including Mauer) tied up in guys who in all likelihood are no longer performing anywhere near an elite level. While I concede it is possible they could all still play at a high level at 35, the odds are much better that they regress, are injured or decline substantially as they age.
I think this is what DieHard is suggesting. The FA signings and other transaction should reflect where the team is in the development/rebuild cycle.
This is exactly what I'm suggesting. Most of those really big FA contracts aren't hunter. They are Kevin Brown type, or the Johan Santana type that does very well in the first couple of years but hamstrings the team later on. There is a time where they make sense, and a time where they most definitely do not make sense. Simply signing guys b/c you have the money is a long term recipie to have a bunch of aging under performing contracts on your plate that you cannot get rid of... Smart, targeted signings when you are one or two holes away from a contender is a completely different case. And yes, as you stated, the odds are not in favor of Ellsbury, Jiminez, and Santana all performing well in the later part of their contracts.
Ellsbury - I'm not sure why he keeps getting bandied around. His OPS was not very good at all this year. His game is speed and that doesn't typically age well, and our OF is already crowded in the short term and long term. Why his name keeps getting brought up here is beyond me. He's a terrible fit, and an expensive one at that.
Santana- fits a position of need. Has a history that indicates durability issues. Is this the type of guy you target knowing that when the offense on this team gets cemented, he could be on the DL with his second TJ surgery, except that he's getting paid 17M/year and that hamstrings your ability to replace him.
Jiminez - He's just inconsistent. Talent is there, but the results don't always show. Also going to be expensive.
I'm all for FA signings, and I honestly think Ryan is too (though he's a bit more risk averse), but in terms of where this team was last year, spending a ton of money makes little sense. The next wave is a lot closer and looks a lot more promising right now, so perhaps it's time to make a plunge, but even then tying up lots of dollars and years isn't smart. Getting that pitching is going to make a lot more sense when the hitting is ready to compete. The only real problem I see is that there are only 3 spots worth filling in 2015 (Meyer, May, and Gibson) and that assumes no one regresses. They will have to make a plunge at one point. The question is when.