Cot's has the Sox on the hook for about 75 million next year. Add in 15 for arbitration and other costs and you're at 90 or so. That leaves them with about 85 million to spend. Spending 24 on Lester does not slow down their efforts to fill out the rest of the roster. In fact, if they don't spend 24 on Lester, chances are they will come in well under the luxury tax limit because the free agent market doesn't have all that much worth spending on in the first place. Let's break this down quickly starting with the offense, since this is the area most in need of help.
Positions they are set at: DH (Ortiz), 1B (Nap), 2B (Pedroia), CF (Bradley and/or Betts), RF (Victorino) and either SS or 3B depending on where Bogaerts ends up.
Positions they have assets to plug into already: SS or 3B (Marrero, Middlebrooks, Cecchini), LF (Nava, Betts, Brentz), and Catcher (Vazquez)
So we are looking at the front office potentially looking for a free agent catcher, a 3rd baseman and maybe a corner outfielder.
Catcher: The best free agent catchers are Russell Martin, Geovany Soto and Kurt Suzuki. All three could also cost a compensation pick, but none of them should be prohibitively expensive. If the Sox have a protected pick, they may be willing to give up their second rounder to fill in that gap or maybe they hope a combination of Vazquez and Butler can get them through enough of the season to fast track Swihart. If they go for a stop gap free agent, it'll probably cost 12-15 million.
3rd Base: This market is kind of interesting. Chase Headley might be worth a make good contract while Cecchini and Marrero spend some time seasoning in The Bucket. Of course, they could also go big after Hanley Ramirez. That's probably at least 25 million a year commitment and most certainly a draft pick.
Corner OF: Melky Cabrera is an interesting option. Nelson Cruz stands out as someone who could be productive, but he's old enough that he'd have to be willing to go short on years. Same with Denofria. After that it gets pretty ugly. Melky is the most interesting name and he's probably going to cost around 15 a year over 4 or 5 years. Basically, a JD Drew contract. His offense is not far off from Drew but he's got the PED suspension hanging from his neck. He'll cost a draft pick as well.
So, even if the team goes against its history and chooses to piss away draft picks to sign one of each, and they go big and sign the best option in each category, you're looking at a total cost of about 55 million a year. Chances are, they'll draw the line at one sacrificed draft pick if they cross that line at all, so it's more likely they would target the best value and call it a day. Even if they go with Hanley, that's only 25 million or so a year and a small fraction of what they have free to play with this coming winter.
Looking at the starting rotation they have Lackey, Buchholz, Doubront, Workman, Webster, DLR and Ranaudo to build a rotation with if they don't bring Lester back. Sure, they could have a decent rotation with those guys, but chances are they want a veteran in the rotation they can count on for a while to be the elder statesman while the kids break in. If it's not Lester they can break the bank for Scherzer. If they won't pay market rates for Lester, I doubt they do it for Scherzer, though. They could look for a value deal in someone like Masterson or Gavin Floyd. Or maybe they take a shot at James Shields. Masterson or Floyd probably ring in at about 15 a year. Shields is probably between that an 20 somewhere.
Unless you think the team is going to let Lester walk and build their rotation without any free agent help, the team is probably spending between 15 and 20 million a year to do so, and they'll end up with a considerably worse pitcher than Jon Lester for their trouble. Either way, I don't see Lester's roster spot or his potential AAV getting in the way of spending on any other pieces they might want come December. I don't think they are likely to go after any of the QO free agents, but they'll have plenty of financial flexibility available if they decide it's worth it.
If they're not going to spend a ton on offense anyway, and they will likely need to replace Lester with a veteran, why not spend a little more on a better bet? I'm just talking about the money they would or wouldn't spend on Lester here. The team is going to spend most or all of it on a replacement anyway, so why not do it on the kid who has been here his whole career, has expressed a desire to stay, is likely to be better than any of the realistic options to replace him and won't cost them a draft pick to replace? A top 50 prospect and the difference between 4-7 or 1-3 in the draft doesn't close the gap between Lester and one of Masterson, Floyd or Shields for me. Especially when you add in the likelihood of having to forfeit a second round pick as part of that move.
