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Previewing the Red Sox at the winter meetings

The Red Sox have a few key to-do items to complete at this year's winter meetings.

Whether Jon Lester comes back to Boston or not, Cespedes will be at the center of winter meetings talk.
Whether Jon Lester comes back to Boston or not, Cespedes will be at the center of winter meetings talk.
Peter G. Aiken-USA TODAY Sports

Major League Baseball's winter meetings begin on Monday, December 8, and continue on through Thursday morning's Rule 5 draft. Unlike last winter, when the defending-champion Red Sox were mostly set and had to work on depth more than bringing in major new pieces, this year's Sox requires pitching, and lots of it. That's going to be the primary focus of the meetings for general manager Ben Cherington and the rest of the Sox, as the lineup is essentially done.

Before the meetings get going -- they're on the west coast this year, in San Diego, so we've got some time to spare before their clocks catch up to those out east -- let's take a look at what the Red Sox hope to -- okay, probably need to -- accomplish over the next four days. There will be offseason after the meetings, of course, so all is not lost if the Sox don't manage to achieve each of these tasks, but with the market expected to move quickly after a certain former Red Sox pitcher signs, the Sox might need to move quickly, too.

Sign Jon Lester

That pitcher is Jon Lester , who is currently negotiating with not just the Sox, but also the Giants, the Cubs, and the Dodgers. Lester was drafted and developed by Boston, and has thrown all but 76-2/3 of his career innings with them as well. The rest came with the Athletics after a midseason trade sent him packing temporarily. At least, the Red Sox hope it was just temporarily.

Lester is as good as anyone else on the pitching market, be they a free agent or a trade piece. He's set to be a relative bargain, as he's younger than James Shields, will be cheaper than Max Scherzer, and won't require the surrendering of major prospects like Cole Hamels would in a trade. The Red Sox can afford to hand him a six-year, $150 million deal, in the sense that they are very rich and can pay their employees vast sums of money, and also in the sense that their lack of long-term commitments and abundance of quality prospects bodes well for the team coming in under the luxury tax threshold in all but the first year of such a Lester deal.

There are no guarantees that he returns to the Red Sox, even if their offer is comparable to that of whoever ends up with him. There are too many other variables to guarantee that: he might want a new challenge, just like the Sox were able to woo Pablo Sandoval away from the Giants with. He might be hurt that the Sox haven't tried to blow him away financially yet. He could still be miffed about either the early season $70 million offer, the July trade, or both. He might have a desire to play for Joe Maddon out in Chicago, or to be the ace of the staff that finally brings the Cubs back a World Series title. Maybe he wants to play alongside Clayton Kershaw so the two of them can have some really cool nickname for both being absurdly talented left-handed pitchers.

Then again, he could want to finish the job he started with the Red Sox with his first nine seasons and two World Series by trying to add more of both while ending up the greatest southpaw the organization has ever seen. He might want to return to the coaching of John Farrell and the only baseball city he's ever truly known. No one knows just what Lester is thinking right now, but he's Boston's Plan A, and everything else will follow his decision.

Post-Lester pitching decisions

If the Sox don't get Lester, then it's time to talk with James Shields, check in with the Phillies on Cole Hamels, or give up on the idea of an ace and start looking for a pair of very strong number two starters to co-lead the 2015 rotation. The Red Sox have the offense to get away with such a plan, and while it's maybe not optimal, it would leave the Red Sox open to hitting the free agent market again with plenty of room left in the budget. Jon Lester won't be there, but Johnny Cueto will be, and he's arguably the most underrated ace in the game.

Expect them to get into the Jeff Samardzija trade talks heavily if they fail to re-sign Lester. The A's are reloading, and the only real competition for Shark to this point is from the White Sox, a team the Red Sox can beat in a battle of prospect resources.

Photo credit: Bob Stanton-USA TODAY Sports

If the Sox do get Lester, then it's time to find the number two starter who will be with the club for at least 2015. They don't necessarily need to figure out who is following Lester in the rotation for the entirety of his new deal or anything like that: just figure out 2015 for now, at minimum, because the Sox have the pitching prospects at the upper level to keep them from having to do more than that. If they can get someone under team control for the next few years, great! But if not, just 2015 will suffice, because the roster is going to see some turnover and a whole lot of money open up a year from now anyway.

Trading Yoenis Cespedes

Yoenis Cespedes is likely to be traded in the next few days. If not during the meetings themselves, then shortly after. The Red Sox will know if they are with or without Lester soon, and once they do, they'll know just what kind of pitcher they need to add. Getting Lester will probably allow them to keep more of their prospects on hand while just dealing Cespedes and his expiring deal to get, at the least, a strong mid-rotation arm capable of 200 innings. If they don't get Lester, Boston might need to shoot a little higher on the pitching market, adding some mid-range prospects to the mix to bump that return from "strong mid-rotation" to "strong number two".

Cespedes is a great addition to almost any lineup, but he is owed $10.5 million and is in the final year of team control. He also cannot be submitted the qualifying offer when his deal ends thanks to a contract stipulation. While there is certainly a market out there for him, if you're expecting to get Mat Latos straight up for him, you're likely delusional. (If someone does give up that kind of pitcher for Cespedes straight-up, they're probably delusional, and this is coming from someone who thinks Cespedes is underrated.)

What's known is that Cespedes is their key trade chip for a starting pitcher, and the quality of that pitcher will likely depend on who else is in the deal, or how much of Cespedes' salary the Sox cover. They have plenty of kids and plenty of cash, so expect them to show off a little of both, especially if they fail to bring back Lester.

The Rule 5 draft

The Red Sox probably won't select anyone in the Rule 5, not unless a super obvious candidate for season-long relief work falls to them. They have already been placing players on waivers or granting them their release in order to make room on the 40-man roster, and have a full 40 as of this writing. If they sign Lester, they'll need to open up another spot. If they trade Cespedes and more, they'll likely have opened up another spot or two, but it's unclear if the Sox have any desire to use that on a Rule 5 player.

It's more likely the Sox will be losing players to the Rule 5 draft than adding them. Pitchers like Noe Ramirez, Miguel Celestino, Keith Couch, and Luis Diaz could all be snagged from the organization and become full-time relievers elsewhere. This would be more of a problem if the Red Sox weren't overflowing with future relievers up and down their system, but they've got a whole lot of those in addition to all the pitchers who still look like their future is in a rotation, and the 40 is loaded with better arms who are closer to ready than these four, anyway.