The Red Sox have always ranked among the league’s heavyweights in terms of financial resources, but throughout the club’s recent five-year rebuild, ownership seemed content to hold back. The Red Sox spoke about sustainability while accepting mediocrity, and every winter they largely sat on the sideline, much to the frustration of the club’s fans.

Last winter that approach began to change.

In 2025 the Sox finally began acting with urgency. The club signed Alex Bregman to a deal valued at $40 million per season, acquired Garrett Crochet in a blockbuster trade and gave him the second largest contract to a pitcher in franchise history, and dished out lucrative in-season extensions to Roman Anthony, Aroldis Chapman and Kristian Campbell.

Coming off the club’s first postseason appearance since 2021, where will the club go from here?

Current payroll

According to Red Sox Payroll on Twitter/X, an invaluable resource that has accurately tracked the Red Sox’s payroll since 2011, the club finished 2025 with a payroll of approximately $248.6 million. That is the highest payroll in franchise history and was also about $7.4 million over last season’s first Competitive Balance Tax (CBT) threshold of $241 million.

The Red Sox only exceeded the CBT once over the previous five seasons, with the lone exception coming in 2022.

Per Red Sox Payroll, the club is currently committed to $218.92 million in salary for 2026. With the first CBT threshold of $244 million next year, the Red Sox will start the offseason roughly $25 million below the tax.

What are penalties for exceeding CBT?

This year the Red Sox will pay a 20% tax on all overages, which would equate to approximately $1.5 million assuming that aforementioned $7.4 million figure.

If the Sox exceed the tax for a second consecutive year in 2026, that tax would rise to 30%.

There are also additional surcharges for exceeding the second, third and fourth CBT thresholds, as well as non-monetary penalties. Tax-paying clubs who sign a player from another team who has rejected a qualifying offer forfeit $1 million in international bonus pool money as well as two draft picks, whereas non-payers only forfeit one draft pick and in some cases $500,000 in bonus pool funds. Clubs also receive a worse draft pick as compensation for losing such players, and if a team has exceeded the third CBT threshold they’ll have their highest draft pick moved back 10 spots.

Who is coming off the books?

The Red Sox have four players set to hit free agency, plus three more with options or opt-outs who are likely to join them.

The former group includes outfielder Rob Refsnyder, left-handers Justin Wilson and Steven Matz, and right-hander Dustin May. The Red Sox reportedly paid those four a combined $9.59 million in 2025.

The latter group includes right-handers Lucas Giolito and Liam Hendriks, who both have rarely exercised mutual options, as well as Bregman, who is expected to opt out of his deal. Factoring in deferred money Bregman carried an average annual value of $31.7 million, which was the highest on the team. Giolito was the club’s third-highest-paid player at $19.25 million, and Hendriks had an AAV of $5 million this past season.

One wild card is Trevor Story, who can opt out of the final two years, $46.66 million of his contract this offseason. If he does, the Red Sox have the ability to void that opt-out by exercising a club option for 2028, which would keep him in Boston for the next three seasons.

How that situation plays out will have a significant impact on the club’s offseason as well.

Any non-tender candidates?

The Red Sox can free up additional money by declining to tender a contract to players who still have years of team control remaining.

Nathaniel Lowe, who is projected to earn $13.5 million in arbitration, is the most likely non-tender candidate. Tanner Houck is another possibility. He is projected to earn $3.95 million but will miss all of 2026 after undergoing Tommy John surgery.

Will any free agents return?

One of the top orders of business for the front office this winter will be keeping Bregman in Boston. The veteran signed with the Red Sox on a short-term, high-dollar deal, and now he will be looking to land the lucrative long-term contract that eluded him last offseason.

The best point of comparison for Bregman is likely Matt Chapman. In March 2024 the Gold Glove third baseman settled for a three-year, $54 million contract with the San Francisco Giants that was structured similarly to Bregman’s with opt-outs after each season. Chapman played well and earned himself a six-year, $151 million extension.

Bregman is the same age now as Chapman was a year ago, and the two third basemen also share agent Scott Boras. It stands to reason Bregman would seek at least as much as Chapman, and if the Red Sox sign him at something approaching that price he would single-handedly bring the Red Sox to the edge of the first CBT threshold, and likely exceed it.

Giolito is a candidate to receive a qualifying offer, which this year is a one-year deal set at $22.025 million. If Giolito rejects the offer and signs with another team, the Red Sox would receive a draft pick after the fourth round as compensation. That would probably be a best-case scenario for Boston given that the club has tons of starting pitching depth and will likely be in the market for a No. 2 starter behind Crochet.

Refsnyder, Wilson or Matz could conceivably re-sign at similar price tags as they carried previously.

Hendriks and May are unlikely to return.

How does Devers factor in?

When the Red Sox traded Rafael Devers in June, they were able to unload all of the salary he was due over the life of his contract. That would have been approximately $29 million annually for the next eight years.

The obvious question after the trade: How would the Sox use that money?

A sizable chunk of those funds have already been reinvested in Roman Anthony, who signed an eight-year, $130 million extension following the trade that will give him an AAV of $16.5 million.

The rest will presumably be spent this offseason, perhaps to help bring back Bregman, sign a power bat, or bring in a No. 2 starter.

Compared to past offseasons where the Red Sox had many needs, this year’s wishlist is short but impactful. Getting all three won’t be cheap, but as long as ownership is willing to tolerate a bigger tax bill there’s no reason why the Red Sox shouldn’t be able to go into next season as genuine World Series contenders.