Red Sox MLB Winter Meetings Blueprint: Analyzing Boston’s To-Do List

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Dec 8, 2014


The Boston Red Sox have entered a critical four-day stretch that could shape the organization’s future.

The Major League Baseball winter meetings began Monday in San Diego, meaning a flurry of transactions — or rumors, at the very least — are bound to surface this week. The Red Sox figure to be at the heart of the activity, as the club still needs to make significant changes before Opening Day.

While World Series aren’t won in the offseason, they certainly can be lost. The Red Sox already made a pair of splashes by signing Pablo Sandoval and Hanley Ramirez, but Boston’s success — or lack thereof — in 2015 will depend on what else the team does this winter. The to-do list remains extensive.

It’s impossible to construct a perfect offseason formula. Sometimes, the best moves end up looking like garbage months and/or years down the road. But it’s pretty clear what the Red Sox need to do — or at least lay the groundwork for — during their next four days on the West Coast.

Boston’s winter meetings blueprint looks like this:

1. Acquire (at least) two starting pitchers
Capt. Obvious has arrived.

The Red Sox’s pursuit of pitching is well-documented. Specifically, their pursuit of Jon Lester is well-documented. But just because the drum has been beaten and beaten and beaten, it doesn’t mean the Red Sox’s need for pitching is any less substantial now than it was at the beginning of the offseason.

Clay Buchholz and Joe Kelly are the only two starters that can safely be penciled into the Red Sox’s 2015 starting rotation. And even they come with questions, as Buchholz was incredibly inconsistent in 2014 and Kelly, while impressive after being acquired from the St. Louis Cardinals, has had some control problems. That means Boston must fill three glaring holes.

The Red Sox have a surplus of young starters, so it’s reasonable to think one rotation spot could be filled internally. Rubby De La Rosa, Allen Webster, Anthony Ranaudo, Brandon Workman, Matt Barnes, Henry Owens, Brian Johnson and Eduardo Rodriguez are the names you’ll hear tossed around. The Red Sox need some stability at the top, however, and Boston’s ideal scenario would involve landing two top-tier starters to slot in ahead of Buchholz, Kelly and Prospect X.

The Red Sox have the flexibility to be creative when it comes to building their rotation. They have the financial wiggle room to make a splash in free agency and the talent pool to build several enticing trade packages. Boston will exhaust all options, but the desired result remains the same.

Click for 10 starting pitchers Red Sox could target >>

Best-case scenario: Red Sox sign Jon Lester and Kris Medlen and trade for Jeff Samardzija.

Lester is the best fit for the Red Sox in free agency, as he’s not only a fantastic pitcher but he’s also a known quantity. The Sox don’t need to worry about any transitional woes. The question, of course, is whether the Red Sox are willing to meet the pitcher’s demands, as it’s going to take a sizable financial commitment to lure the left-hander back to Boston.

Jeff Samardzija shouldn’t be the Red Sox’s primary target. He also shouldn’t be viewed as an “ace” as Boston constructs its rotation. But the Red Sox and Athletics have conducted business several times in recent years — July being the most obvious example — and Boston seemingly has the pieces to pry Shark out of Oakland. Samardzija could be a very good No. 2 starter in a rotation anchored by Lester.

Kris Medlen is a wild card coming off his second Tommy John surgery. Whichever team signs the 29-year-old should temper its expectations, but he’s an intriguing free agent, to say the least, especially if he can be signed to a one-year, incentive-laden contract. Medlen went 15-12 with a 3.11 ERA with the Atlanta Braves in 2013 before missing all of 2014 with an elbow injury.

2. Add to the bullpen
The Red Sox have several young pitchers who could transition into relief roles in 2015, but Boston still will look to add to its bullpen, especially after losing out in the Andrew Miller sweepstakes. Craig Breslow and Burke Badenhop both are free agents, creating at least two spots the Red Sox must address.

A reunion with both or either isn’t out of the question. Breslow, in particular, is a good fit for Boston despite his lackluster 2014. Perhaps he could iron out things under a one-year deal with the Red Sox.

In any event, the Red Sox must consider adding both a lefty and a righty. Tommy Layne and Drake Britton are the only two southpaws vying for spots in a bullpen currently comprised of Koji Uehara, Junichi Tazawa, Edward Mujica and whichever young hurler(s) becomes a reliever. Steven Wright and Alex Wilson also are part of the conversation, though the Red Sox are better off relying on them as organization depth.

Best-case scenario: Red Sox sign Pat Neshek and Joe Thatcher.

Neshek was one of the best relievers in baseball this season, meaning he could be in line for a multiyear contract. But if the Red Sox can obtain the right-hander on a reasonable two-year pact, he’s absolutely worth considering despite his unorthodox delivery and previous battles with injuries. Neshek is a strike-throwing machine who showed an ability to retire both right-handed hitters and left-handed hitters with the St. Louis Cardinals in 2014.

Thatcher is similar to Breslow in that he’s coming off a down season. The 33-year-old lefty has comparable splits against left-handed hitters, though. He represents a nice option if the Red Sox have concerns about re-signing Breslow.

3. Acquire a backup catcher
Christian Vazquez figures to be the Red Sox’s starting catcher in 2015. It’s imperative that Boston adds a viable veteran backup, though, as Vazquez still is young in his development. Growing pains are a possibility.

David Ross hit free agency this offseason, and reports suggest he’s garnering plenty of interest on the open market. It’s even been rumored that he could be part of a package deal with Lester and go wherever the left-hander signs.

Best-case scenario: Red Sox sign David Ross.

The Red Sox probably would prefer to add a catcher who hits left-handed and has more offensive upside, especially since there still are questions about Vazquez’s offensive potential. But the catching market is very, very thin, particularly in free agency.

The Red Sox could try to pry the left-handed-hitting Alex Avila away from the Detroit Tigers. If they can’t, they should strongly consider a reunion with Ross. While Ross struggled in 2014, he’s among the game’s best leaders, which is important with Vazquez taking over in Boston and top prospect Blake Swihart developing down on the farm.

4. Sort out the outfield
This likely will happen intrinsically through whatever the Red Sox do on the trade market. It’s still worth noting because the Red Sox seemingly have about 8,000 outfielders vying for three spots.

Best-case scenario: Red Sox leverage their outfield depth to acquire pitching.

Thumbnail photo via Greg M. Cooper/USA TODAY Sports

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