How the Red Sox Can Compete in 2020

Boston Red Sox
Mandatory Credit: Photo by ADAM DAVIS/EPA-EFE/REX/Shutterstock (9947204bi) Boston Red Sox players celebrate after defeating the Los Angeles Dodgers in game five of the World Series at Dodger Stadium in Los Angeles, California, USA, 28 October 2018. The Red Sox win the series 4-1 to become the World Champions of Major League Baseball. Boston Red Sox at Los Angeles Dodgers, USA – 28 Oct 2018

The next Red Sox GM will have his hands full with the amount of issues the Red Sox face heading into the 2020 season. It seems as though nobody even wants the job, which I understand. The Red Sox would be facing serious penalties if they continue to stay above the $208M luxury tax. The 2019 Red Sox had $254M go against the luxury tax. The next GM will have to find a way to cut payroll while building a competitive team for 2020 and beyond. Dave Dombrowski did exactly what was asked of him, he made the big moves needed in order to win a World Series. However, much like when he left the Tigers, the Red Sox are in shambles heading into a critical off-season for the future of the Boston Red Sox.

Luxury Tax Issues Facing the Red Sox

According to Spotrac, the Red Sox will have $134M allocated to players already under contract for the 2020 season that will count towards the luxury tax. This number is assuming that J.D. Martinez does in fact opt-in to his contract. If you add all expenses, including medical expenses and benefits, we are looking at about $151M for next season. That number does not factor in all arbitration eligible candidates. Here is a list of the arbitration eligible players, along with their projected salary for the 2020 season by MLB Trade Rumors, who are known to be accurate with their projections.

Mookie Betts – $27.7M

Jackie Bradley Jr. – $11M

Eduardo Rodriguez – $9.5M

Andrew Benintendi – $4.9M

Brandon Workman – $3.4M

Matt Barnes – $3.0M

Chris Owings – $3.0M

Sandy Leon – $2.8M

Heath Hembree – $1.6M

Steven Wright – $1.5M

Gorkys Hernandez – $1.0M

Marco Hernandez – $700K


Projected Arbitration Salaries Total: 70.1M

– $5.5M = 64.6

With these players’ contracts added to the current payroll, Boston will be sitting comfortably over the $208M luxury tax threshold. I marked the players I believe are not likely/not worth bringing back next season. I would be stunned if the Red Sox tendered contracts to Chris Owings and Gorkys Hernandez, as neither player was able to make an impact on the 2019 Red Sox.

Steven Wright could make the team in 2020, but I personally have seen enough from the inconsistent knuckleballer who keeps finding new ways to stay off the roster. He is currently battling an elbow injury after missing time for an 80 game PED suspension as well a toe injury and various knee issues. Wright pitched a whopping 6.1 innings in 2019, which feels replaceable, especially given his 8.53 ERA during that span. Taking those players out we are now looking at $215M, and we still have to go over pre-arbitration salaries (baseball finances are confusing). 


Fortunately for the Red Sox, the MLB is against paying young players, even if they had borderline MVP caliber seasons. Rafael Devers .311 with 32 HRs and 115 RBI’s. Unfortunately for Devers, he will not be making nearly as much as Manny Ramirez next season, who is still being paid for the contract he signed a millennium ago. Judge has become one of the leagues brightest stars, yet he is making $684,300 for the 2019 season. Devers, Chavis, Darwinzon Hernandez and a slew of fairly irrelevant fringe roster candidates will add a few extra million on the Red Sox tab. Let’s make this easy and say that the Red Sox are at roughly $220M in luxury tax allocations.

* Boston is still responsible for paying that obese bum Pablo Sandoval a $5M buyout, but that does not affect the luxury tax. The Red Sox are also still paying Manny Ramirez roughly $2M, but that is waived from competitive balance rules as well.

Red Sox Free Agents

The Red Sox will have some shoes to fill, even if Martinez and Betts end up staying in Boston. Here are the Red Sox unrestricted free agents for the upcoming off-season: SP Rick Porcello, 1B Mitch Moreland, 1B Steve Pearce, and UTL Brock Holt. Porcello has done a lot for the City of Boston, but he should not be missed after an abysmal 2019 season. He won a Cy Young and a World Series with the Red Sox. Unfortunately, we cannot afford to pay him for his prior accomplishments in Boston or else we will have two Eovaldi contracts on our hands.

First and second base is a mess right now. Moreland is almost assuredly gone, as well as Steve Pearce. I’m sure that both would be interested in returning, but we are struggling to pay people in-house right now. Michael Chavis could certainly take the reins if Boston did not have a hole to fill at second-base as well. Jose Abreu and Edwin Encarnacion are quality free agent options, but the Red Sox aren’t exactly looking to spend. If Martinez leaves then those two become legitimate options, but they would not be the most ideal use of the Red Sox payroll. At second-base, Dustin Pedroia is still under contract at a hefty $13.75M price tag. It remains to be seen if he can even get on the field this year, and he is hurting the Red Sox ability to construct a contender this off-season.

How The Red Sox Can Free Up Some Payroll

Trading Jackie Bradley Jr.

Image result for jackie bradley jr catch

Bradley has been surrounded by trade rumors for years. While his defensive abilities are unmatched, people are increasingly frustrated by his lack of offensive production. I was never on the side of dealing JBJ in the past, as he has been undervalued on a yearly basis. I would rather have one of the best outfielders on the planet than someone like Puig, who was a potential acquisition last season. Home runs are great, but he saves more extra-base hits than most outfielders can hit. The problem with his perception is that offensive statistics are shown every single time he is at the plate, and defensive metrics are not featured for the most part.

That being said, he is projected to make roughly $11M next season, and the Red Sox are strapped for cash (with one of the highest payrolls in baseball). Boston could start to rebuild their farm system with Bradley on the move. This move would be favored if Martinez returns next season, otherwise we would be rather thin in the outfield.

Placing Dustin Pedroia on Waivers

This move would hurt a little, as someone who watched Pedroia struggle entering the league before taking it by storm. If the Red Sox put the beloved second-baseman on waivers, he would be removed from the 40-man roster. People who are no longer on the 40-man do not count against the luxury tax. Pedey would still get his money and a shot at a comeback, but it would not impact the Red Sox ability to reconstruct the roster. Pedroia is owed 13.75M in 2020, which is currently counted towards the luxury tax. No team team would dare take on that contract for a player battling his knee issues, meaning he would stay in the organization. We made a similar move with Rusney Castillo years ago.

If he were to come back and produce, the Red Sox could potentially make some moves to clear up enough payroll to bring him back. That seems unlikely given his current state, but knowing Dustin, he fully believes he has at least one more productive season in him.

Could The Red Sox Keep Martinez and Betts?

The Red Sox could in theory keep both Martinez and Betts with just a few transactions. Jackie Bradley Jr. would have to be dealt which should put the Red Sox right around the luxury tax threshold. Retaining Betts, Martinez, and Benintendi would lessen the impact of a JBJ trade.

In this scenario the Red Sox would likely have to place Pedey on waivers, which would give them some options. That would put them at around $195M in luxury tax allocations before making any moves. They could go back and re-sign Holt to fill that void at second along with Marco Hernandez. Chavis could move to first full-time and they may have some room to acquire a starter to replace Porcello at a reasonable cost. I’ll go over some other realistic scenarios, but this would be my plan of action if I were to take the reins as the Red Sox President of Baseball Operations.

One Major Variable: J.D Martinez

This off-season has one major variable: J.D. Martinez. He has to decide whether he is going to stay in Boston or move on after just two seasons.

Martinez Opts-out:

If Martinez opts-out then the Red Sox should keep Mookie for the time being and use the slight financial flexibility to fill some holes. This feels like the most likely scenario, with multiple players moving on this off-season. I believe that J.D. would love to play in Boston, but he does not want to be a part of a team that is likely about to trade their MVP. We do not have the ability to replace J.D. with another marquee free agent, but we could at least build a competitive roster. Another 108-win season is not in our near future, but we can still compete for the American League East.

The team saw a lack of production by the entire pitching staff, but there is not much the team can do about it. Sometimes it just comes down to the fact that certain players need to be better. Sale and Price need to stay healthy and the bullpen has to execute better. The Red Sox do not need 40 homers from Marco Hernandez, they just need their aces to hit their stride and for guys like Barnes to remember how good they can be. If the season pans out like it did in 2019, Boston would trade Mookie Betts at the deadline and rebuild our core around Bogaerts and Devers. Betts is not coming back without testing free agency first, and the Red Sox probably will not have the financial flexibility to pay an MVP caliber player next off-season either. 

Martinez Opts-in:

This would be a slight surprise to me, but it is possible. Martinez has another option at the end of the 2020 season, so he could give it one more run in Boston. The Red Sox would either have to move Mookie in the off-season or shave off money elsewhere. Trading Mookie in the off-season would give the Red Sox some room financially and allow for the team to trade for MLB-level talent. As much as everyone loves prospects, Betts is too good to give up for an unproven talent. Teams will not trade away MLB talent in the middle of a playoff run, but they will before the season starts, especially for Mookie Betts. This might be the best solution for the 2020 Red Sox and beyond.

As hard as it would be to see Mookie in another uniform, it would allow the team to fix some issues that we could not fix otherwise because we are paying Nathon Eovaldi $17M to be completely average and injury prone. He was rewarded heavily to pitching multiple innings in a game we did not even win. I am a fan of Eovaldi but the Red Sox giving him a massive extension was foolish.

If the Red Sox were to deal Betts in the off-season and put Pedroia on waivers, the team would be sitting at roughly $180M. They would have $28M to play with this off-season. The Red Sox could easily bring back Holt and bid for a quality pitcher, someone like Hyun-Jin Ryu or Dallas Keuchel who will be tasked with pitching as well as 2018 Rick Porcello. Both players are capable of doing so, at relatively cheap price tags.

What if we lost Martinez and Betts?

This is most Red Sox fans biggest nightmare. It would be a clear blow to the offense if we lost both stars this off-season. If Martinez opts-out, we still will be on the watch for a blockbuster trade featuring Mookie Betts. It would make the most long-term sense to get a package for Betts, though it would not be a guarantee. The Nationals made a run during Harper’s last season knowing he would be testing free agency the following off-season. The Red Sox are talented enough to attempt a similar run, hopefully with better results. The Red Sox would then be about $35M below the luxury tax. They could easily bring Martinez back on a restructured deal with more years and less average annual value. Martinez appears to be the type of player that will not break down like most players entering the latter stages of their career.

Everything Will Work Itself Out

Fortunately for the Red Sox, we will not see a full rebuild as long as the soft cap stays in the MLB. Somehow we are still seeing entire 40-man rosters worth $60M. As long as that does not change, the Red Sox worst-case scenario is that they become bottom-feeders for a few seasons before making another run at a title.