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Boston Red Sox: Five biggest questions this offseason

By Sean Penney

Sep 17, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski looks on during the third inning against the New York Yankees at Fenway Park. Mandatory Credit: Winslow Townson-USA TODAY Sports
Sep 17, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski looks on during the third inning against the New York Yankees at Fenway Park. Mandatory Credit: Winslow Townson-USA TODAY Sports /
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Jul 5, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski speaks on the phone prior to a game against the Texas Rangers at Fenway Park. Mandatory Credit: Mark L. Baer-USA TODAY Sports
Jul 5, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski speaks on the phone prior to a game against the Texas Rangers at Fenway Park. Mandatory Credit: Mark L. Baer-USA TODAY Sports /

Will Dombrowski cash in more chips from the organizations deep farm system to make another blockbuster trade?

Sean: Hopefully not. The core of this team is built upon players that came up through the system, which is working out pretty well so far. Dombrowski has to be careful not to deplete that pipeline of cost controlled future stars much further than he already has. Free agency would be the best path to finding a slugger to fill the DH void and a power arm for the bullpen, so a blockbuster trade is only necessary if they strike out on the open market.

Brandon: It’s possible. One never wants to go all in for a championship if it’s going to hurt the team in the long run. Some other organizations are going through that problem right now. Yet, the future of the Red Sox is pretty much already on the active roster, many of them playing starting roles for the team. The entire starting outfield and the shortstop will be with the Red Sox for a very long time, and players like Moncada are close to taking the reigns as well. If some prospects who are still developing are playing positions already filled by these young men, then Dombrowski may consider using those chips in a trade package. As long as he doesn’t touch the core of this youth movement, Dombrowski should have a free hand.

Rick: Boston has somewhere around the 5th ranked system and they do have a few players that others certainly will find attractive.  If – and it is a big if – the Red Sox wish the services of Sale they will have to part with a few prospects. If I was Chicago I’d want at least two and a few major league ready players, such as JBJ.

Matt: If he can get a top of the line starter, yes he’ll do it. But I think it’s more likely to happen at the deadline or even next offseason.

Next: Is Buchholz coming back in 2017?

Chance: I could certainly see Kopech or Devers being sent somewhere in order to cash in on someone big. Who for? I couldn’t tell you. But I feel like if the Red Sox make moves in free agency regarding the bullpen, and Shaw settles in at third, the front office will feel more comfortable dealing Kopech or Devers somewhere else.

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