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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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.

BOSTON, MASSACHUSETTS – SEPTEMBER 08: Starting pitcher Rick Porcello #22 of the Boston Red Sox pitches at the top of the first inning of the game against the New York Yankees at Fenway Park on September 08, 2019 in Boston, Massachusetts. (Photo by Omar Rawlings/Getty Images)
BOSTON, MASSACHUSETTS – SEPTEMBER 08: Starting pitcher Rick Porcello #22 of the Boston Red Sox pitches at the top of the first inning of the game against the New York Yankees at Fenway Park on September 08, 2019 in Boston, Massachusetts. (Photo by Omar Rawlings/Getty Images) /

The Red Sox have a hole in the back-end of the rotation with Rick Porcello hitting free agency. While there is interest in bringing him back to Boston, there are definitely other options on the free agent and trade market.

Free agents that are available include pitchers such as Tanner Roark, Wade Miley, Dallas Keuchel, Martin Perez, among others. With the health definitely being the primary weakness of the starting staff, the Red Sox need a starter who can eat lots of innings.

Also, with the bullpen failing at the beginning of the season due to fatigue from the stress created by the lack of innings pitched by the rotation, the Red Sox need a fifth starter in the worst way. Porcello is a great choice as he flashed his potential in 2016 by winning the AL Cy Young and averaging just shy of 200 innings a season during his tenure with Boston.

It will be interested how Chaim Bloom deals with adding depth to the starting rotation as he shouldn’t divert too much money there as he needs to allocate it to other areas of the team. On the other hand, improving the starting rotation could inadvertently make the bullpen pitch better for the entirety of the regular and hopefully, postseason.

Prediction: Red Sox bring back Rick Porcello on an incentives based deal

FORT MYERS, FLORIDA – FEBRUARY 19: Bobby Dalbec #83 of the Boston Red Sox poses for a portrait during Boston Red Sox Photo Day at JetBlue Park at Fenway South on February 19, 2019 in Fort Myers, Florida. (Photo by Elsa/Getty Images)
FORT MYERS, FLORIDA – FEBRUARY 19: Bobby Dalbec #83 of the Boston Red Sox poses for a portrait during Boston Red Sox Photo Day at JetBlue Park at Fenway South on February 19, 2019 in Fort Myers, Florida. (Photo by Elsa/Getty Images) /

Mitch Moreland and Steve Pearce have left the Red Sox, creating a spot at first base. With Bobby Dalbec, a popular choice to win the 2020 American League Rookie of the Year, set to come up next season, will Chaim Bloom opt to pair him with a veteran bat?

With players on the free agent market like Edwin Encarnacion, Travis Shaw, and C.J. Cron, Bloom could pair the young slugger with one of those options. Dalbec has lots of power (.221 ISO), but an unstable bat (139 SO). Pairing him with a veteran on a 1-year deal could benefit the youngster as he can learn from their experience.

A move like this would be similar to bringing in J.D. Martinez after the 2017 ALDS defeat to the Houston Astros. If Encarnacion were brought in, he could be a complementary piece that can mentor Dalbec and consequently, the whole team.  While Dalbec has enough talent already to be a successful player for the Red Sox, pairing him with an experienced player to mentor him for one season definitely wouldn’t hurt.

Another possible option is Michael Chavis. He was forced to learn a new position, second base, in 2019 due to the injuries to Dustin Pedroia and Brock Holt, while Eduardo Nunez was eventually released.

His offensive numbers slipped as he posted a 96 OPS+. Chavis displayed enormous power, but a swing and miss bat which left him prone to hot and cold streaks, along with plentiful strikeouts. He ended up playing a solid second base, so he could get the job headed into 2020. However, if the Red Sox feel his offensive decline was a result of playing second base, he could be shifted back to first base.

Prediction: Red Sox entrust Bobby Dalbec with a full-time role in 2020

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

ST PETERSBURG, FLORIDA – JULY 24: David Price #10 of the Boston Red Sox pitches during a game against the Tampa Bay Rays at Tropicana Field on July 24, 2019 in St Petersburg, Florida. (Photo by Mike Ehrmann/Getty Images)
ST PETERSBURG, FLORIDA – JULY 24: David Price #10 of the Boston Red Sox pitches during a game against the Tampa Bay Rays at Tropicana Field on July 24, 2019 in St Petersburg, Florida. (Photo by Mike Ehrmann/Getty Images) /

With rumors swirling that the Red Sox would prefer to hold on to Mookie and instead cut a starter such as Price or Eovaldi, the question is if Bloom will be able to find a trade partner. Both pitchers would be tough to move as they both under-performed in 2019.

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Price pitched less than 110 innings, while Eovaldi’s ERA was nearly 6.00. The southpaw will make $96 million over the next three seasons, while the right-hander will make $51 million. It will certainly be tough to move them coming off of those statistics!

It does seem as if there are trade partners out there, though. The Rangers expressed an interest in acquiring one of the starters at the beginning of the offseason, but those talks have seemed to simmer down since. However, it does show that teams are taking a serious look at the Red Sox starters.

Teams that need a veteran starter and don’t want to give up many (or any) top-prospects in a trade might want to acquire Price. The Twins could have interest as they were in on Zack Wheeler who ended up signing with the Philadelphia Phillies. Eovaldi could garner interest in analytically savvy teams such as the Astros. They could unlock his potential as they did with Gerrit Cole when he was brought in from the Pittsburgh Pirates.

Prediction: Astros acquire Nathan Eovaldi from Red Sox to fill Cole’s spot

ST PETERSBURG, FLORIDA – SEPTEMBER 23: Mookie Betts #50 of the Boston Red Sox is congratulated after scoring a run in the fourth inning during a game against the Tampa Bay Rays at Tropicana Field on September 23, 2019 in St Petersburg, Florida. (Photo by Mike Ehrmann/Getty Images)
ST PETERSBURG, FLORIDA – SEPTEMBER 23: Mookie Betts #50 of the Boston Red Sox is congratulated after scoring a run in the fourth inning during a game against the Tampa Bay Rays at Tropicana Field on September 23, 2019 in St Petersburg, Florida. (Photo by Mike Ehrmann/Getty Images) /

Oh boy, the question everybody knew was coming. Will the second or third best player in baseball be traded? This question may very well loom over the Red Sox for as long as Boston keeps the former MVP.

He is one of the best players in baseball and he will be payed like one in 2020 as he is set to make just shy of $28 million, per MLB Trade Rumors. The Red Sox need to cut payroll and trading Mookie could be the only way.

If teams choose not to relieve the Red Sox of one of their starters, the payroll will be very high headed into 2020. Betts can instantly upgrade any team and transform their rebuild into postseason success. Teams this apply to are the Cincinnati Reds, Chicago White Sox, and San Diego Padres – all of whom have been coincidentally linked to the right fielder, along with teams like the Los Angeles Dodgers, Atlanta Braves, and New York Mets.

However, a surplus of reports this week have indicated that the Red Sox will have a difficult time trading the 3-time silver slugger as he is set to make a load of money in 2020 and only has one year left of control. Other star players such as Francisco Lindor and Kris Bryant have a greater chance of being traded as they both have two years left of control.

Next. Trade proposals for Jackie Bradley. dark

Overall, the Red Sox would likely pull the trigger if they found the right trade for Mookie, but not many teams have the correct combination of prospects and payroll flexibility necessary to acquire the services of the homegrown Boston star.

Prediction: Mookie stays with Boston for 2020

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