chrisfont9 said:
As for how bad a 6/120 deal would be for the Sox to make, I guess it's a precedent Cherington may be uncomfortable with -- we all saw how quickly the Epstein Era went from holding the line to giving out (rather awful) megadeals. But if the expectation now is that at least two or three of the young arms will come through over the next five years, doesn't that make an overpay rather affordable? It assumes you let Lackey finish out, which seems pretty safe; that Doubront sinks or swims, but in either case is a few years away from getting a big payday and will probably be someone you can part with when he hits free agency; and that Buchholz is either living up to his potential and forcing a tough decision, or continuing to miss time and perhaps a bit more affordable or easier to let go of. By contrast, the Yankees' rotation already has two megadeals, and adding a third probably wouldn't hurt them too much but may prevent them from adding a fourth or fifth.
Really, though, for me I just don't know if I can stand seeing Lester in pinstripes. My judgment is 100% colored by this. Sorry.
I've been giving this question some thought.
After a brief lull since the Papelbon/Ellsbury/Lester/Buchholz/Bard/Lowrie days, it's tremendous that the farm system has gotten back to producing useful young players in bunches (Nava, Xander, Bradley, Middlebrooks, Doubront), with more (Cecchini, Betts, a whole passel of young pitchers and catchers!) seemingly on the way. As we saw with the '07 club, perhaps the best Red Sox team ever, getting high-level production from pre-arb players is a key ingredient in roster construction. That pretty much goes without saying.
Farm productivity gives the team some flexibility to spend big money on some high-ticket items, especially as the Gomes/Victorino/Napoli/Peavy/Lackey/Sizemore deals age out of the budget. That leaves a core of Ortiz/Buchholz/Pedroia/Bogaerts/Bradley, supplemented by (optimistically) two of the young SP, Vazquez, Swihart and Middlebrooks and/or Cecchini. That's a pretty affordable core. That group will only cost something like $50m for nine or ten roster spots in 2016, for a DH, 2B, SS, CF, 3 SP, two catchers, and 3B.
I'm thinking in terms of the 2016 roster because that is the final year of the current CBA, and thus — if history is any guide — likely the last year of the $189 soft cap.
That leaves $130m-ish for the remaining fifteen spots. Those spots need to include a 1B, LF, and RF (unless one of those is Cecchini), two more SP (of whom one could be Doubront in his Arb2 year), bench IF (Betts?) and OF, one more bench player and a seven-man bullpen (which would likely include Tazawa and some number of the pitching prospects). That's an average of about $9m per roster spot for those fifteen spots, of which we're likely to fill at least four or five with pre-arb players. Basically, for each year of a pre-arb player we can add, we can have a $20m FA-type player during that year.
So I think it would be very possible to spend big to keep Lester in the continuing core, while also paying retail to add a high-impact bat by FA or trade (say, Giancarlo Stanton for one of the corner OF spots), and still come in well under the $189 threshold. But there are only so many big contract bullets in that gun: likely two or three. So Cherington needs to decide if Lester makes sense as one of those guys, or if he prefers other players. I think I would probably do it, in his shoes.
(Of course, if the injuries keep coming and the offense keeps "hitting" like it has, the question will be whether Cherington should deal Lester to the Mariners at the deadline for Dustin Ackley and Danny Hultzen.
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