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Red Sox Winter Meetings: Predictions for five biggest questions

By Tim Starr

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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ANAHEIM, CA – AUGUST 30: Mookie Betts #50 of the Boston Red Sox rounds third base after hitting a home run in the first inning against the Los Angeles Angels at Angel Stadium of Anaheim on August 30, 2019 in Anaheim, California. (Photo by John McCoy/Getty Images)
ANAHEIM, CA – AUGUST 30: Mookie Betts #50 of the Boston Red Sox rounds third base after hitting a home run in the first inning against the Los Angeles Angels at Angel Stadium of Anaheim on August 30, 2019 in Anaheim, California. (Photo by John McCoy/Getty Images) /

With the Winter Meetings underway, the Red Sox and Chaim Bloom have lots of questions to answer, so let’s give predictions for those five questions.

With 2020 possibly being the end of the Mookie Betts era, the starting rotation’s health will be a question mark for the duration of Chris Sale‘s contract, and a young core of Xander Bogaerts and Rafael Devers still in place, the Red Sox are in an interesting position this offseason.

With new Chief Baseball Officer Chaim Bloom now taking over and entering his first Winter Meetings with Boston, he has to do a lot with a little. A flurry of trades could be made, similar to the past decade when he’s been with the Tampa Bay Rays.

With the goal set by Red Sox ownership to cut payroll and eventually get under the luxury tax, Bloom has a challenging task ahead of him. Cutting payroll AND getting a team back to the postseason is quite the quest for the first-time Chief Baseball Officer.

There are probably (a lot) more questions that the Red Sox front office needs to answer this offseason and it all starts with these Winter Meetings. Lets analyze and predict answers for the five biggest questions that face Boston this offseason.

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