Red Sox Winter Meetings: Predictions for five biggest questions

BOSTON, MA - SEPTEMBER 27: John Henry, Tom Werner and Larry Lucchino share a laugh as Lucchino was being honored for his last home game as Red Sox CEO/President before a game against the Baltimore Orioles Fenway Park on September 27, 2015 in Boston, Massachusetts. (Photo by Rich Gagnon/Getty Images)
BOSTON, MA - SEPTEMBER 27: John Henry, Tom Werner and Larry Lucchino share a laugh as Lucchino was being honored for his last home game as Red Sox CEO/President before a game against the Baltimore Orioles Fenway Park on September 27, 2015 in Boston, Massachusetts. (Photo by Rich Gagnon/Getty Images)
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BOSTON, MA – JUNE 13: Matt Barnes #32 of the Boston Red Sox reacts after making the third out in the eighth inning of a game against the Texas Rangers at Fenway Park on June 13, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA – JUNE 13: Matt Barnes #32 of the Boston Red Sox reacts after making the third out in the eighth inning of a game against the Texas Rangers at Fenway Park on June 13, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)

With members of the Red Sox front office already declaring that they’d like to upgrade the bullpen, the question is who will Bloom bring in. He could bring in a top arm such as Dellin Betances or Will Harris, or get a less expensive free agent such as Sergio Romo or Steve Cishek.

I believe the Red Sox can have a dominant bullpen in 2020 if the correct piece are added. With Darwinzon Hernandez, Matt Barnes, Josh Taylor, and Brandon Workman sure to come back and build off of their 2019 seasons, and a rotation that can’t possibly get worse, they could have a good bullpen in 2020.

If the four relief arms mentioned prior could all set up to a new closer such as Betances or Harris, they have a chance to have a bullpen comparable to teams such as the Yankees or Astros – both of whom have dominant relief pitchers.

However, a series of lower-end options such as Romo or Cishek could save the Red Sox payroll and by signing several buy-low options, if one works out it would be successful. However, this strategy didn’t work as Dave Dombrowski proved in 2019. Jeurys Familia, Colten Brewer, and others all failed in 2019. With the more analytical approach by Bloom though, this strategy could work.

Prediction: Red Sox sign Will Harris to be 2020 closer

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