Red Sox Analysis: Boston's Free Agency Shopping List Must Include High-End Starting Pitcher, Third Baseman Pablo Sandoval, Plus More This Offseason

November 3, 2014

By Matt Straub


A year ago this column was easy. The Boston Red Sox were coming off a World Series championship and had very few holes to fill going into the 2014 season. But a funny thing happened on the way to a title defense. The Red Sox fell apart, panicked about a bad year and ended up gutting their roster. This leaves Boston with a lot of shopping to do this winter as it tries and restock for another run in 2015. There aren’t as many kids in the minor league system ready to contribute as there once was or will be in a year or two, so I believe Boston will do a lot of shopping this season rather look for things already in their closet.


The Red Sox had a strong rotation they could rely on, so of course they traded most of it away in July. They do have a number of young pitchers who will make contributions in 2015, but they need to get front-line starters if they’re going to compete for a playoff spot. There are also questions at third base and in the outfield, which is strange since the team has a ton on outfielders already. Every team has to add to its bullpen in the winter, and the bench is always rotating, but needs to be settled for a team to truly contend. The Yankees, for example, were gutted with injuries in 2014, but managed to make it until the final weeks of the season because they had enough pieces to fill holes.


So let’s take a look at where Boston could find some new toys to buy this winter and what gifts they could give their fans in the holiday season.



The Red Sox had a good one. Jon Lester and John Lackey were solid, Jake Peavy was a battler and a number of kids made up the back end of the rotation to provide depth and something to look forward to in the future.


By September, the Sox had one pitcher, Clay Buchholz, left from their initial rotation. The year was lost, and Boston tried to reshape the trade deadline by getting major leaguers back and added depth to the lineup in the process instead of waiting years for future prospects to develop and getting no immediate help in return for their best players.  


Unfortunately, that left only Buchholz, and if you’ve read my rants about Buchholz here, you know he didn’t exactly do well this season. He simply cannot be the ace next year if the Red Sox are going to contend. I’d much prefer him to not be part of the 2015 rotation at all, but that seems unlikely at this point. Joe Kelly, the pitcher Boston got for Lackey, will be back and is a decent option for the middle or back of the rotation. Rubby De La Rosa is to me the best piece Boston has among its own talent which will be ready next year, though you’ll see more of their minor leaguers as spot or fifth starters.


Boston’s ability to compete in the future, however, depends on what they can get for the top of the rotation. They will make a big push for Jon Lester, but I can’t imagine him signing now when the Red Sox couldn’t work out a deal during the year, when he was willing to stay for a hometown discount. The Red Sox don’t want to give long-term deals to aging pitchers, which I get, but how many young stars are out there to get? You have to spend money to get production. The other name being thrown around is James Shields, who has a checkered playoff history, unlike Lester. Shields, by the way, will be 33 in December. If you’re going to give money to an aging pitcher, why not give it to Lester, who is a little younger and a stud in the postseason?


They’re also talking about trading for Cole Hamels, but why give up prospects when you can just give up money and keep your young talent? Lester is the guy to get here. If not, and I don't see him coming back, then I’d rather see them try to get Max Scherzer than Shields or a trade for Hamels.


Whatever move they make, however, at least one of those pitchers has to be on the roster come March.


One of those stars, plus Kelly, De La Rosa and Buchholz at the back of the rotation is a nice start. From there you can use your other young players and a mid-range signing or two such as Justin Masterson to fill out the staff.



The Red Sox did the right thing getting Koji Uehara back at a reduced rate. He can still be a great closer, but he must have his innings limited now as he passes 40 and fell apart late last year. Koji was 26-of-28 in save chances before the final six weeks or so, when he collapsed and was eventually removed from the role.


He can be good again, but he will need more help to get to the end of the season. The Red Sox need a backup closer of sorts, which is why paying Andrew Miller the $8 million or so he’s expected to want is worth it. The guy is a big lefty, has proven he can be dominant in the eighth inning and playoffs, and can likely can handle some ninth-inning pressure. Sign him, use him in the eighth and sometimes in the ninth to take some load off Koji, and shorten the game the way the Royals did this year.


Signing Miller should be priority one in the bullpen.


Craig Breslow is thankfully gone, but the Sox shouldn’t let Burke Badenhop get away. The Red Sox need to maintain some strengths in the sixth and seventh since the starters in the rotation I envision might not get too deep into games, and he would be a big help. Junichi Tazawa always scares me but is a solid piece, and the Red Sox have plenty of middle inning type of guys they can use for depth. Adding another good lefty would help, maybe Luke Gregerson, but Boston needs Miller first.



Mike Napoli will be back, but he might be in decline. The Red Sox could use Allen Craig there to spell Napoli at times, though Craig was awful this year as well. If one of those two doesn’t pick it up, the position could be a hole next year. They should try and get a solid bench player, preferably a lefty, but there isn’t much out there. The Sox are stuck hoping what they have works.



Last winter I said the Sox needed to get a strong backup for Dustin Pedroia, who showed why this year by getting hurt again. His decline in production in recent years is mostly due to injury, but he needs a caddie at this point. Brock Holt is an important piece and Mookie Betts is still an option for the future since he’s only being converted to the outfield because Pedroia is there at second. I’d have Pedroia on other people’s shopping lists, but that’s highly unlikely. What you see is what you get here.



Hopefully the same applies to short. Xander Bogaerts has shown he doesn’t handle shuffling and change well, but he’s too good to be hassled. Just leave him in the role and let him grow up. He hasn’t gotten anywhere near his prime yet, let him get there without worry.



Let’s make this short and sweet: Will Middlebrooks struggled and was uncoachable. He’s a bust and the Sox need to get him out.


Even simpler is the solution: Pablo Sandoval. There are other options, but a 28-year old switch-hitter who is beloved by his fans and clutch in the postseason is the ideal fit. He’s going to cost a lot and the Red Sox will have to make sure he stays in something resembling shape, but he can always slide over to first or DH when David Oritz eventually retires and Napoli's deal ends.. He’s not as good as Ortiz, but he is one of the best fits for the Red Sox in a while, especially in an organization which loves selling things, which Sandoval will do. The Sox are likely already dreaming of panda heads for kids and various t-shirts. This is the easiest call of them all. Pablo Sandoval has to be in Boston next year. Overpay him and get it done.



The Red Sox won’t be shopping for an outfielder because they don’t know what to do with all the ones they have. Shane Victorino might be back from injury, Rusney Castillo has to play so the Sox can find out if he's for real, and Yoenis Cespedes has a year left, though the skids already seem to be greased for his departure. Perhaps the Sox can trade him as part of a blockbuster deal instead of someone like Betts, who needs time in the outfield as well, unless Pedroia is hurt or gone.


The more likely solution here is a trade which gets rid of an outfielder, not brings one in. Trade from your surplus and get a need, like a pitcher.


And we haven't even touched on Jackie Bradley Jr., the all-world glove who can't hit. Boston either needs to play him every day and let him figure out how to hit or cut bait now. He could eventually be a defensive replacement if it comes to that, but you can't make that move until you know exactly what you have.


I have a feeling the logjam of outfielders is settled in some kind of winter trade which nets a pitcher or third baseman.


Read our Red Sox Pay Him or Slay Him column here


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