A Wishlist for the Red Sox Offseason


The Red Sox have several difficult decisions to make for 2020. Here’s what I’d like to see them do.

The Red Sox are in a tough position. They failed to make the playoffs despite having the highest payroll in all of baseball. The disappointing season – combined with the need to scale-down the bloated budget to offset Luxury Tax penalties – led to the firing Dave Dombrowski, the team’s President of Baseball Operations. Dombrowski, known throughout the league as a big spender, brought Boston a championship and cemented his legacy. He did his job. But now, a rebuild is needed, and Dombrowski simply isn’t the man to make that happen. Simply put, the Red Sox offseason will be interesting, if nothing else.

Now the organization is in the hands of Chaim Bloom, a young, savvy executive who spent his career with the Tampa Bay Rays. On paper, it’s an excellent match. Bloom has been noted for his creativity and ability to operate on a budget. He helped field a great team in Tampa Bay, with the Rays forcing the Astros to a Game 5 in the ALDS while operating with the lowest payroll in baseball. Once the Red Sox have cut payroll and reset the luxury tax, it’s exciting to think about what he could do with the resources of a premier, large market organization that is already one of the best of the 21st century.

Along with hiring a new GM and minimizing costs, the Red Sox face several challenging questions. Will 2020 be Mookie Betts‘ final year in Boston? Who should be given contract extensions, and who should be allowed to walk away? In this article, I’ll break down everything, and provide a blueprint the team could follow.

Establishing a Baseline

To answer these questions, we have to establish certain parameters. The luxury tax is going to factor into every single decision the organization makes this offseason. Ownership has already made it clear that getting below the tax is the top priority. To evaluate the moves the Red Sox will make, one must understand the tax situation.

The Competitive Balance Tax kicks-in when teams surpass the league’s soft salary cap. In 2019, the cap was $206 million. Every dollar spent above the cap gets taxed. When teams surpass the cap in consecutive years, the tax rate increases accordingly. For first-year offenders, the rate is 20%. For second-year offenders, it rises to 30%. Surpassing the threshold three years or more triggers penalties of 50%. As an added bonus, exceeding the cap for three straight years moves a team’s top draft pick ten spots back.

Clubs also receive a 12% surtax for exceeding the cap by $20+ million. Exceeding the threshold by $40 million or more increases the rate to 42.5%. When a team gets under the salary cap, the tax rate resets. It drops back to 20%, taking effect the next time that team exceeds the cap.

In August, the Commissioner’s Office calculated that the Red Sox had a payroll of $242.8 million in 2019. Because the team exceeded the salary cap for two straight years, they face a base tax of 30%. They also incurred the 12% surtax for exceeding the cap by $20+ million. That adds up to a tax rate of 42%. They were a mere $3.2 million away from surpassing the $40+ million threshold. Doing so would’ve increased the tax rate to 88.5%. As it stands, the Red Sox will pay roughly $12 – $13 million in luxury tax for 2019.

If you’re still confused by the luxury tax, or you’d like to do some deeper research, here’s an in-depth piece by Alex Speier of the Boston Globe.

Looking to 2020

According to Baseball Reference, the team will have a maximum guaranteed payroll of roughly $146 million for 2020. That amount includes a final $5 million payout to Pablo Sandoval, and salary for Dustin Pedroia ($13 mil). Paying off Panda’s contract will be a relief: Boston has owed him over $36 million since the team released him in 2017.

The salary cap will increase to $208 million in 2020. The guaranteed $146 million leaves the Red Sox $62 million to work with. On paper, that sounds great! Sign Mookie Betts to an extension! $35 million for 2020! But then, you have to factor in arbitration salaries. Per MLB Trade Rumors, there are nine players on the Red Sox with a projected total arbitration salary of $64.6 million.

The guaranteed and projected arbitration salaries add up to $210.6 million. It might only exceed the cap by $2.6 million, but surpassing it for the third year in a row will trigger the final tier of the tax penalty: 50%. That is why it is so important to get the payroll reined in now. The salaries also leave no room for additional player signings. Starter Rick Porcello, utility-man Brock Holt, and first basemen Steve Pearce and Mitch Moreland are entering free agency. Pearce is likely going to retire. Those holes must be filled if the Red Sox want to remain even remotely competitive.

Offseason Wishlist

So these are the parameters that the Red Sox will be working under in the offseason. Every decision will be calculated to ensure the best outcome for 2020 and beyond. Now, the challenge is to build the best team possible with these limits. This will include trades, free agency deals and re-signings.


Jackie Bradley Jr.

Losing Bradley would be a big blow. He’s been a staple of the Red Sox outfield since 2014 and is one of the best centerfielders in baseball. He single-handedly crushed Astros pitching in the 2018 ALCS. He’s also projected to win $11 million in arbitration, per MLB Trade Rumors. Trading JBJ to a team in need of a good outfielder is one of the fastest, easiest ways to get under $208 million. While the outfield will suffer, especially if Mookie Betts leaves, it’s one of the best ways to keep the payroll from the cliff.

David Price

David Price
(AP Photo/Tony Dejak)

Another move that would hurt, but it simply needs to happen, would be to find a suitor for David Price. Price has a guaranteed $32 million coming his way in 2020; that’s the highest salary on the team, even if Mookie Betts wins his arbitration case for $30 million. He will earn that amount every year until he reaches free agency in 2022. That’s a tremendous overpay, and one of Dombrowski’s biggest missteps in my opinion. Price is a good pitcher, and a huge reason the Red Sox won in 2018. He still isn’t worth $32 million a year.

Trading Price might be the most efficient way to clear the salary cap, but it also might be the most challenging. There aren’t many teams who would jump at the chance to take on an aging starter who has upwards of $90 million left on his contract. If the Red Sox wanted to accomplish this, they’d probably have to subsidize the deal or sweeten the pot by attaching a second star player to the trade.

Mookie Betts

I know, I know. “How could you? He’s a top-five player in baseball, and you want to trade him?!” I get it. Believe me, I don’t like it either, but just hear me out. Mookie’s walk year is in 2020. He has made it abundantly clear he wants to reach free agency. The man wants a paycheck. He’s earned the right to make as much money as he can.

The thing is, Betts is with the club until next year and could make $30 million in arbitration. The Red Sox need to cut payroll right now. Because of the rebuild, Mookie’s final year in Boston may not even be that exciting. The Red Sox could forgo competing in 2020. If they do, why not send him to a team with World Series aspirations for a year? The Astros come to mind. Would they rather have Josh Reddick, who is a fine player, or Mookie Betts? Would the Brewers jump at the chance to have an outfield with Betts and Christian Yelich?

Maybe the club can attach Price to a Mookie trade. Moving Betts and Price in a package deal could save the Red Sox $60 million in 2020. Once the team has reset the luxury tax, there’s nothing that says they can’t simply approach Betts with a new contract once the season ends. They could do what the Yankees did with Aroldis Chapman in 2016.


However the Red Sox choose to get below the luxury tax, there are still holes to be filled. Signing a decent, durable starting pitcher would be in the team’s best interest. If Price gets traded and the new arm saves the team a few million dollars, even better. With that in mind, here are some free agent starters the Red Sox could sign.

Jake Odorizzi

Jake Odorizzi

Odorizzi is coming off of a good year with the Twins. The right-hander posted a 3.51 ERA with a 1.208 WHIP. His 3.36 FIP was a career mark. His 178 strikeouts were a career-high, and he issued a respectable 53 walks. He had an excellent 10.1 K/9 and a solid 3.0 BB/9. He’s never made $10 million a year, but he should easily make $15+ mil starting next year. The Red Sox should consider offering him a two year, $34 million contract.

Dallas Keuchel

Dallas Keuchel only played half a year in 2019 after the veteran southpaw signed with the Braves in June. He went on to have a decent season, posting a 3.75 ERA with a 4.72 FIP. His 1.367 WHIP was average. Keuchel might choose to re-sign with the Braves, but there’s a higher chance he will look to be paid in free agency without the qualifying offer attached to him. It’s highly likely he doesn’t want to wait until June to sign with a team again, which the Red Sox might be able to take advantage of. They should offer him a one year, $13 million contract.

Zack Wheeler

Zack Wheeler
(Photo by Sarah Stier/Getty Images)

Probably the least likely option here, but you never know. Wheeler has had a couple of fine years with the Mets. He threw a combined 377.2 innings in 2018-19, posting a 3.65 ERA with a 3.37 FIP. Most of the attention this offseason will go towards Gerrit Cole and Stephen Strasburg, but Wheeler should make some good money for himself. While Wheeler’s market will probably be more competitive than Keuchel’s, the Red Sox shouldn’t be afraid to offer him a deal for two years, $35 million.

Re-signings / Extensions

Don’t let the disappointment of 2019 distract you from the fact that the Red Sox have an elite core with enormous potential. Some of the players walking away should be offered contract extensions. Keeping the chemistry intact would simply be smart business.

Brock Holt

Brock Holt

Is Brock Holt a star player? No. Is he a crucial fixture in the line-up or on the field? No. But he is important nonetheless. Holt’s value isn’t in his talent or abilities. His value is in his character: he always has a smile on his face, he’s a media darling, he’s the team’s moral compass and everyone’s best friend. It isn’t difficult to imagine a scenario where the clubhouse culture suffers in his absence.

In addition, the work he does off the field as the Captain of the “Jimmy Fund” is unparalleled, and it shows: he’s been hailed as the best liaison between the two organizations since they began their partnership in 1953. Brock Holt is important, both to the team and to the city. Offering him an extension worth two years, $12 million should be one of the easiest decisions the ownership makes this year.

Sandy Leon

Why not? Leon is a great pitch framer, and he’ll come cheap. You can’t ask Christian Vazquez to kneel behind the plate for all 162 games. The Red Sox will need a backup catcher, and the team knows exactly what they’ll receive from Leon. Extend him an offer for two years, $7 million.

Brandon Workman

Brandon Workman

After the tremendous year Workman had in 2019, this move just makes sense. He’s in his final year of arbitration, and he’ll enter free agency next season. The Red Sox would be wise to lock him up for the long term while they have the chance. If he continues his success next year, even with a downgrade, his free agent value will be high. Signing him to a 3 year, $18 million deal would be in everyone’s best interest.

Rafael Devers

Rafael Devers
(Photo by Michael Ivins/Boston Red Sox/Getty Images)

Another move that seems obvious and makes a lot of sense. Rafael Devers will enter his first year of arbitration next year. He had one of the best years in history for a 22-year-old, that’s simply a fact. Ownership should do what they should’ve done with Mookie Betts: sign him long-term early. It’s a win-win for both parties. Devers would earn life-changing money without having to drag through arbitration negotiations. The Red Sox get a great value on the deal in return, assuming Devers maintains a steady level of production. Fellow third baseman Alex Bregman signed a five year, $100 million extension prior to the start of the season. Devers obviously isn’t on Bregman’s level yet, but it’s a good starting point.

Rick Porcello

Porcello’s entire season hit rock-bottom. He was the worst qualified starting pitcher in baseball by ERA. Why bother with him? Because he hit rock-bottom – meaning it would be difficult for him to have a worse year. The Red Sox will need pitching help, especially if they trade Price. Porcello is a solid pitcher, 2019 notwithstanding. If nothing else, he’s reliable. He threw 174.1 innings in 2019, and 191.1 the year before. In fact, he’s never had a single season where he threw less than 160 innings.

Porcello also stated he would take a discount to stay in Boston prior to the start of the 2019 season. Given his wish to stay in Boston, they could easily offer him a one year, $6 million contract. It’s low-risk, high-reward. If he accepts and has a bounceback year, the team gets good value on a decent pitcher while Porcello can enter free agency with re-established value.

Tom is a Red Sox and Patriots fan. He graduated from Fitchburg State University with a Bachelor’s Degree. He’s a David Ortiz and Xander Bogaerts enthusiast. You can follow him on Twitter @PrimeJD.

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