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If the Dodgers sign Jon Lester, what do the Red Sox do?

Besides sob quietly, we mean.

Cole Hamels is just one of many plans the Red Sox could enact if Lester signs elsewhere.
Cole Hamels is just one of many plans the Red Sox could enact if Lester signs elsewhere.
Eric Hartline-USA TODAY Sports

Plan A for the Red Sox in the 2014-2015 offseason has been "Sign Jon Lester" ever since it became clear that in-season negotiations were not going to lead to anything. With the Dodgers now reportedly entering the Lester fray, the chances of the Red Sox bringing the lefty they drafted and developed back to Boston haven't evaporated, but they have dropped. With that in mind, it's time to consider what Plan B could or should be should Lester head west, and while we're at it, maybe a few more plans as well. You know, just in case.

Plan B: Trade for Cole Hamels

We've discussed in this space many times that Cole Hamels is the backup plan for Jon Lester. Lester was the preference not only for Boston's familiarity with him, but also because he would only cost money. Hamels will cost prospects -- great ones, even -- and on top of that is owed $22 million per season, which isn't all that far off from what Lester is expected to pull in. He's still worth it, of course, but when you can pick between Lester and Hamels in these scenarios, the preferred choice is obvious.

Hamels has four years and $90 million left on his deal along with a $6 million buyout for his 2019 option, but it's become public knowledge that a trade to Boston would necessitate picking up the option, turning it into a five-year, $110 million deal. As Hamels is on the same level as both Lester and Max Scherzer, that's a bargain just in contract terms. If he ends up costing the Red Sox six years of Mookie Betts along with some other prospects in the process, though, it becomes a less attractive option overall. Still, it could be a necessary one, if the plan is to have an ace atop the rotation again as soon as 2015.

The Red Sox could fit Hamels into their budget just about as well as they could fit Lester in over the next five years, with one major difference: If Betts is dealt, the Red Sox then need to either start Daniel Nava or Allen Craig in the outfield in his place in the future, or go out and sign a new outfielder, whose price and identity are obviously unknown. Nava remains inexpensive and combined with Hamels would basically cost what Lester does, and Craig's $6.2 million average annual value is a palatable one for luxury tax purposes, but an upgrade on the free agent market could be far more expensive, limiting what the Sox have to spend elsewhere. Plus, Betts could end up being better than either of those players, as well as whoever is brought in instead.

At the same time, however, the Sox would have Cole Hamels and therefore a legitimate ace, and on the relative cheap from a dollars point of view. There is a whole lot of value in that, even if Betts ends up turning into the real deal in Philadelphia, and it's something worth considering for the Sox.

Plan C: Double up on Number 2 Starters

Maybe the Sox decide they don't want to give up Mookie Betts, Blake Swihart, or whichever major prospect(s) the Phillies are lusting after for Cole Hamels, even if he is an ace. It would be more of a problem if not for the influx of number two starters -- some of them almost overqualified for that designation -- available on the trade market. Ken Rosenthal reiterated on Thursday morning that the Nationals have Jordan Zimmermann and Doug Fister both available for trade in the last year of their deals. The Mariners might be willing to part with Hisashi Iwakuma in the final year of his contract for the right return. The Athletics are dangling Jeff Samardzija now that they've sent Josh Donaldson to Canada. The Reds haven't decided if they are rebuilding or going for it just yet, but it's possible that one of Mat Latos or Johnny Cueto could be had. Cueto is actually an ace and maybe doesn't belong in this plan since he'll require better prospects, but since he's only under contract for one more year instead of five, he fits here more than on the Hamels' side of things.

The current plan for the Red Sox is to acquire one of these pitchers -- or someone fitting a similar description -- in addition to Lester. Yoenis Cespedes is the logical trade piece here, as he's also in the final year of his deal and is one of the top bats available this winter, whether through trade or free agency. Maybe the plan should be to move Cespedes for a number two starter as planned, but also to pick up a second number two. The Sox wouldn't have an ace, but with the lineup they are currently planning on trotting out, they might not necessarily need one.

A rotation with a pair of twos atop it followed by Joe Kelly, Rubby De La Rosa, and Clay Buchholz has a lot of potential. Kelly is just a league-average starter, and De La Rosa might also only be that, but another year removed from 2013's physical problems might be just what Buccholz needs to get back to usefulness. If that's not the case, and Buchholz is horrible again, there is nothing requiring that he sticks in the rotation all year: the Sox still have Henry Owens and Eduardo Rodriguez sitting in Triple-A, and one or both could be ready for the bigs before much longer. Matt Barnes and Brian Johnson are also around, just to show how much insurance there is to cover for not just injuries, but as Plan B for Buchholz.

Part of the beauty of this plan, outside of retaining prospects like Betts and Swihart, is that the Red Sox would have first crack at extending these number two types before they hit free agency. Doing so would help them avoid the higher end of the free agent market for the next four or five years, and would also guarantee -- well, the baseball version of guarantee -- some stability at the top of the rotation while the incoming prospects finish fine-tuning and adjust to the realities of facing major-league hitters. As the Red Sox have already shown with Sandoval and Ramirez, they don't mind these $90-100 million deals for great players who aren't necessarily elite, and number two starters would fit that mold as well.

Plan D: Sign James Shields

This is a good time to say that these plans aren't ranked in order of attractiveness to the Red Sox: all of them have their pros and cons, none of them are as appealing as simply signing Lester, but one of them has to be enacted if the Sox plan on contending in 2015. James Shields is a great pitcher, an underrated one, even, but he's also a few years older than Lester and Hamels, and will be 33 in the first year of what will presumably be a four- or five-year deal. This won't help the Red Sox from an average annual value perspective all that much, but it does help them avoid going to six years, as they would with Lester, or giving up prospects, as they would for Hamels.

Photo credit: Peter G. Aiken-USA TODAY Sports

Shields will cost the Red Sox a draft pick in 2015, but that's less of a concern right now than it used to be, considering the Sox gave up their first two available picks already to sign Pablo Sandoval and Hanley Ramirez. Normally that in itself would be a concern, but Boston's first-round pick, the seventh, is protected, so they aren't shut out of the first few rounds by any means.

Like with Hamels, part two of this plan would be to trade Cespedes for a number two starter. It's a good plan! More suitors for Shields will show up the moment Lester signs, though, so just like with the lefty, the Sox are not guaranteed to bring Shields home. More plans are necessary!

Plan E: The lineup looks pretty great. Right?

Okay, maybe this final plan is ranked in order of attractiveness, because it's certainly the one that would cause the most distress to Red Sox fans heading into 2015. This is the one where the Sox trade Cespedes for Number Two Starter To Be Named Later and then supplement that trade with the signing of a non-ace starter, someone like Brandon McCarthy or Ervin Santana, once Santana realizes that sometimes being better than average does not entitle you to five-year deals unless you want to be Ricky Nolasco's teammate in Minnesota.

This is also where the Sox can try to sign some depth options to save their kids from coming to the rescue, or sign Gavin Floyd on the cheap since his most recent elbow injury was a freak fracture and not a ligament issue. Maybe offer Brandon Morrow a make-good deal, try to pry Brandon Beachy from the Braves as he works his way back from his own elbow issues... there are all kinds of risks to take here, but also very clear opportunities. And not every single one of them involves signing a former Braves' starter, either!

This is obviously the emergency plan, one where pieces of it should be filtering into other, better plans, one where it should probably not be The Plan. If the price for Hamels is too high, though, and both Lester and Shields sign elsewhere, and the Sox can't convince the Nationals or whoever to part with that second number two starter, then this is where they'll end up. It's not a terrible place to be, by any means, it's just not the optimal one. The Sox could probably hit enough to get away with it, but in an AL that is loaded with quality teams, betting on something more than "probably" is preferred.


Plan A, Jon Lester, remains the top option for both the Red Sox and most of those watching from home. After that, the Red Sox have some choices to make. Do they want to spend just money for an ace, or is Hamels worth the prospect cost on top of what's left of his deal? Do they only want to venture into the ace market when a known quantity like Lester is involved? Should they just try to acquire some expiring number two types to get the inside track on signing them to an extension instead? Almost none of this will even be a question if Lester simply returns to Boston, but with the Dodgers now involved in the proceedings, that's far from a given.