Red Sox: Five biggest offseason questions heading into December

BOSTON, MASSACHUSETTS - SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS - SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
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BOSTON, MASSACHUSETTS – SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS – SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

With numerous payroll and roster questions still surrounding the Red Sox,, lets analyze the five biggest question marks that Chaim Bloom has yet to answer.

This offseason will define the Boston Red Sox for years to come, maybe even the next decade. The best player not named Mike Trout could leave the Red Sox this offseason because John Henry doesn’t want to pay the luxury tax to keep Mookie Betts.

David Price currently holds the record for the largest starting pitcher contract in major league history. Guess what, he could be on the move this offseason as there were previously numerous rumors about the Texas Rangers having interest in acquiring a Red Sox starter. There was a report from Ken Rosenthal that Jackie Bradley Jr. would “all but certain” not be playing for Boston come 2020. Is he still on the trading block or has something changed?

Clearly, the Red Sox have been a hot topic this offseason as there have been numerous rumors and reports surrounding the team. They are a win-now team that has to financially operate like the Oakland Athletics except their is no roster depth.

Chaim Bloom has a lot of work to do this offseason so lets analyze five questions he must answer heading into December.

BOSTON, MA – AUGUST 9: Jackie Bradley Jr. #19 of the Boston Red Sox runs to first base after hitting a two RBI single in the sixth inning against the Los Angeles Angels at Fenway Park on August 9, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley/Getty Images)
BOSTON, MA – AUGUST 9: Jackie Bradley Jr. #19 of the Boston Red Sox runs to first base after hitting a two RBI single in the sixth inning against the Los Angeles Angels at Fenway Park on August 9, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley/Getty Images) /

Who will be non-tendered?

The Red Sox roster is spoiled with players going through arbitration this offseason. In order to increase financial flexibility on the payroll, some players who are making too much money may get non-tendered. Obviously, players like Betts (projected $27.7 million in arbitration per MLBTR) won’t get cut, but others might. The deadline to non-tender a player is December 2.

A few players who the front office may choose to cut are Jackie Bradley Jr. (projected $11 million per MLBTR), Sandy Leon (projected $2.8 million), and Heath Hembree (projected $1.6 million). These players seem to be expendable on the roster and would not be franchise changing to cut.

JBJ has had rumors swirling about him and he may also be traded. If the Red Sox are not confident they can trade Bradley, they will cut him and not pay $11 million for a below-average offensive player. If teams are interested in the center-fielder’s services, then he will likely be tendered a contract only to trade him.

Leon is a backup catcher and is likely overpaid. His 2019 OPS+ was 42 which was absolutely atrocious. The Red Sox tried to cut him last season as he started the season in Triple-A. He was only called up because he is Chris Sale‘s personal catcher. However, Sale may be forced to pitch to Vazquez or an external replacement next year as $3 million for Sandy may not seem worth it to the now penny-pinching Red Sox.

Hembree was having a solid season in 2019 until it got spoiled by an elbow injury. With his health definitely being a concern for next season, a minor-league pitcher can almost definitely put up similar numbers for about $1 million less.

Overall, while all three of these players have contributed greatly over the past several years, the Red Sox need to save every penny and some complementary, arbitration-eligible players may have to be casualties. Either way, the Red Sox front office only has a day left to make this decision as the deadline is on Monday, December 2nd.

Prediction: Red Sox non-tender Heath Hembree and Sandy Leon, tender Jackie Bradley Jr. a contract

OMAHA, NE – JUNE 28: Third basemen Bobby Dalbec #3 of the Arizona Wildcats hits an RBI single against the Coastal Carolina Chanticleers in the first inning during game two of the College World Series Championship Series on June 28, 2016 at TD Ameritrade Park in Omaha, Nebraska. (Photo by Peter Aiken/Getty Images)
OMAHA, NE – JUNE 28: Third basemen Bobby Dalbec #3 of the Arizona Wildcats hits an RBI single against the Coastal Carolina Chanticleers in the first inning during game two of the College World Series Championship Series on June 28, 2016 at TD Ameritrade Park in Omaha, Nebraska. (Photo by Peter Aiken/Getty Images) /

Who will be the starting first baseman?

Two free agents, Mitch Moreland and Steve Pearce, are set to leave Boston in free agency this offseason. With very little chance to bring back either of the aging first baseman, the Red Sox have to figure out the situation at first. There are a few intriguing internal options and some external options could help fill the roster hole.

First of all, and the most probable option, is bringing Bobby Dalbec to the majors. The slugger was recently added to the 40-man roster which could signal his major league debut in 2020. He mashed nearly 30 home runs this past season which accurately conveys his excellent power. A few years of development and Dalbec could be a middle of the order bat for Boston. If this happens, Michael Chavis would be the second baseman.

A second option is moving Chavis to first base. He basically split his time between second and first last season and it may have contributed to his offensive decline as the season went on. He had to learn a new position (second base) and combined with the rigor a second baseman has to play with may have taken his focus away from hitting. He also had a season-ending injury in August due to a diving play at second.

This option would block Dalbec so he would become a trade chip or he would have to learn a new position. Marco Hernandez would probably take over second base (or Dustin Pedroia, you never know). This option seems the least likely because it blocks Dalbec from the majors and Hernandez hasn’t proven that he is an everyday ballplayer.

A third and final option is bringing in an external addition to play first. This also seems unlikely because the signing/trade would have to be a left-handed bat (there aren’t many left-handed first baseman available) because they would end up platooning with Dalbec. Also, this would likely be an upgrade that the Red Sox should not prioritize. A first baseman likely costs around $7 million per year and that money could help a bullpen that could use it.

Overall, the most likely option is that Dalbec takes over at first base while the Ice Horse plays second base. Chavis should improve at second because he has a whole winter to learn the new position.

Prediction: Dalbec plays 1B/Chavis plays 2B

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) /

What pitching upgrades will be brought it?

The 2019 Red Sox bullpen was shaky. Somehow the rotation was even worse. The Red Sox big four starters averaged less than 132 innings and now they are losing Rick Porcello who averaged just under 32 starts a year in his time with Boston.

Let’s start off with the hole in the bullpen. The Red Sox have a much better talent than they get credit for as Brandon Workman, Matt Barnes, and Darwinzon Hernandez could make a dominant trio. With a supporting cast consisting of Ryan Brasier, Josh Taylor among others, the Red Sox could use one top arm to stabilize the top of the bullpen.

If a pitcher like Dellin Betances or Will Harris is brought in, they could close for the Red Sox in 2020. This takes away stressful innings from the rest of the bullpen and allows them to be put in high-leverage situations. With Red Sox owners already confirming they hope to upgrade the bullpen this winter, let’s hope they acquire a top-end reliever as opposed to a depth piece that ends up collapsing in 2020. A Tyler Thornburg or Carson Smith repeat is the last thing that the club needs, especially after the 2019 drag.

In the rotation, unlike the bullpen, the Red Sox don’t need a top-end starter, rather just an innings-eater. A pitcher like Porcello perfectly fits Boston’s needs. He has shown he won’t completely collapse when pitching in Boston, but was always reliable, accountable, and took the ball every fifth day. Other starters on the market include Tanner Roark or Gio Gonzalez.

If the Red Sox wanted to use internal options (which is a terrible idea) they could use pitchers like Hector Velazquez or Brian Johnson. Both have been spot starters and reliable depth pieces for the club, but both had ERA’s above 5.40 last season. They are nice depth pieces, but not fifth starters for a team with postseason aspirations.

Overall, I have always been a Porcello defender and I think he could return on a cheap 1-year deal. He will eat innings and was sharp in the 2018 postseason which shows that he won’t succumb to pressure.

Prediction: Red Sox re-sign Rick Porcello to a 1-year deal, sign Will Harris to a 3-year deal

BOSTON, MA – JULY 30: David Price #10 of the Boston Red Sox pitches in the second inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA – JULY 30: David Price #10 of the Boston Red Sox pitches in the second inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images) /

Who will be traded?

Rumors have surrounded Red Sox players this entire offseason. While none of the rumors have come to fruition, it seems like a trade is on the horizon. A number of players who have been talked about are Mookie Betts, Jackie Bradley, David Price, and Nathan Eovaldi. All of them are set to make a decent amount of money that the Red Sox would be happy to shed. I wrote an article earlier in the offseason describing five trade candidates Boston has.

Mookie is set to make $27.7 million in arbitration in 2020, per MLB Trade Rumors, and he has been reluctant to sign a long-term contract. Reports have indicated he and the Red Sox have yet to have discussions regarding a contract extension to stay in Boston.

His desire to enter free agency and earn every cent he can may be his exit ticket out of Boston as the Red Sox are tight on payroll. Personally, I don’t think Betts should be dealt because he is a franchise-changing player and you build your team around that player, you don’t build around the players he brings back in a trade.

Also, I’m skeptical a club will fork over a haul of prospects for Betts as he only has one year of control and is set to make a hefty payday in 2020. The Red Sox front office may be so determined to cut payroll they will create another Curse of the Bambino if they trade Mookie. Let’s just hope he is in Boston for the rest of his career.

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Another trade option is JBJ. He will make north of $10 million in arbitration which is not great for a player who was 10 percent worse than league average last year. I believe that a center fielder that is strong defensively is very important to a winning ball-club, but the Red Sox can’t be handing over serious amounts of money for a player that provides little to no offensive value. This is a similar situation as to Sandy Leon at catcher.

Ultimately, Bradley’s fate comes down to Betts. If the 2018 MVP is traded, Jackie will likely stay. If the Red Sox come to their senses and keep Mookie, it is still no guarantee JBJ is traded, but it definitely raises the chances. Cutting the 2018 Gold Glove award winner to keep Betts would be a small price to pay.

Price and Eovaldi are both in similar situations as far as their status in Boston. Both are signed for three more years and both are making serious money for those three years. Eovaldi makes $17 million a year, while Price makes $32 million a year. Both garnered interest early in the offseason from the Texas Rangers, but those rumbling have seemed to die down. Unless a team is willing to eat a significant amount of money on either of these contracts, both will begin 2020 with the Red Sox.

Overall, the Bradley and Betts situation kind of depend on each other as only one will most likely  be traded as to not leave a huge hole in the outfield.

Prediction: Red Sox keep Mookie Betts, trade Jackie Bradley Jr. to the Cleveland Indians

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) /

Will the Red Sox go for the postseason or cut payroll?

This offseason will show the priority of the Red Sox front office. Trading Betts and cutting other players in order to save on the luxury tax would signify that they are going to try and cut payroll. Sticking with this core and hoping they can replicate the magical 2018 season shows that winning is still the number one priority.

Paying a small tax to keep stars like Betts is definitely worth it as he is a once in a lifetime talent. I believe the Red Sox will ultimately realize there is no way to completely avoid paying the luxury tax this season, but a more realistic plan would to be shave little bits of payroll, such as cutting JBJ, and make the goal to get under the tax in a year or two.

While I am concerned that Chaim Bloom was brought in to begin a rebuilding process and reload for a few years, I am still confident the Red Sox will be contenders in the 2020 season. With a rotation that should come back strong, an improved bullpen, and a powerful lineup, the Red Sox won’t be able to avoid the luxury tax.

Next. Where will Red Sox rank in AL East?. dark

Altogether, I don’t think the Red Sox will be able to cut all of the payroll they want as they will still try to win. Similar to what Andrew Friedman did with the Dodgers, the Red Sox will be contenders for many years while still paying lots of money in the present.

Prediction: Red Sox will pay the luxury tax in 2020 in order to remain contenders

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