How Much Will John Henry Spend on the Red Sox in 2026?
Is there a way to build a championship roster while also keeping the Boss happy?
The Red Sox are a big market team. There was a time when they acted like it. Even before John Henry, Dan Duquette pulled off a bold trade with the Expos for Pedro Martinez and signed Manny Ramirez to a huge deal. These were the building blocks for the championship years. When Henry bought the team, he let Theo Epstein acquire star players such as Curt Schilling and Josh Beckett. The result was championships. Four of them.
The Competitive Balance or “Luxury” Tax (CBT) is a limit that, when exceeded, kicks in penalties that are meant to discourage high spending by big market teams. The interesting part of this is that the salaries that factor into the CBT are average annual values (AAV), not the players’ actual salaries for any given year. For example, Roman Anthony’s salary goes from $2M in 2026 to $29M in 2033, but his CBT hit for every one of those seasons is his AAV of $16.25M.
The Twitter feed of Red Sox Payroll (@redsoxpayroll) is a great resource when trying to understand how the Red Sox have spent over the years. The following table is from RSP’s worksheets:
When Dave Dombrowski was in charge of the team starting in 2016, he was allowed to spend over the CBT soft cap significantly. In 2018 and 2019 they exceeded the cap by about $40M each year. Dombrowski was then fired in the middle of the 2019 season. Since then, the Red Sox have generally been under the cap, although they did exceed the CBT by almost $8M in 2025. Does this signal a return to spending like a big market team? This offseason will tell the tale.
After the Sonny Gray trade, the Red Sox sit at $225M, or $19M below the first CBT line. (There are actually several CBT tiers spaced $20M apart, but we won’t delve into that detail. I also won’t attempt to calculate the penalties as that is fairly complicated). So, here’s the big question: How much payroll will John Henry green light in 2026?
I am going to predict that John Henry will approve a payroll of $255M, which is $11M above the first CBT threshold. This is a slight increase over last year and I think he feels that it shows that he is willing to spend to win. For comparison, the Dodgers payroll last year was $400M (not including CBT penalty), the Mets $328M, and the Yankees $310M. The Red Sox spend nowhere near these teams. Even the Blue Jays spent $267M last season and just signed Dylan Cease to a huge $210M contract.
So, what can Craig Breslow do with a $255M payroll? With only $19M in payroll flexibility, he will need to get creative, but it is certainly not impossible to build a championship roster. My suggestions:
Phase 1 – The Fan Favorite
Pete Alonso is projected to get a 4 year/$110M contract, let’s call it $28M AAV. Joe Ryan’s AAV this year is $6M. Let’s assume you trade Jarren Duran and his $8M AAV for Ryan. That’s a total addition to the payroll of $26M and would put it at $251M. Would John Henry do that? I see no reason why he shouldn’t. You get your #2 starter and one big bat. They could definitely stop there but you still have holes to fill and not much payroll left.
Phase 2 – Wheel and Deal
In order to meet your other needs, you will probably have to make more trades. How do you shed salary? Players who could be trade candidates are Trevor Story ($23M), Masataka Yoshida ($18M), Jordan Hicks ($12M), Brayan Bello ($9M), and Patrick Sandoval ($9M). If Breslow can shed the salaries of Story and/or Yoshida he is a rock star, but that will be very tough to do. Hicks, Bello, and Sandoval are much more tradable.
Bo Bichette and Alex Bregman will each command a $26M AAV. Assuming that you now have your #2 and #3 starters in Ryan and Gray, do you really need both Bello and Sandoval? Can you find trading partners for them? Same question for Jordan Hicks who was terrible in 2025. Again, I think this is doable for a savvy executive.
Let’s assume you can pull off a trade for Hicks and Sandoval and take back prospects. You can free up $21M in payroll. Sign Bichette or Bregman for $26M. That puts you at a $256M payroll, right where John Henry wants to be (in my scenario).
Is this Fantasy Island? In Red Sox Land it probably is, but a good GM should be able to pull off this scenario or something similar. There must be a way to get the players you want and keep the payroll where John Henry wants it.
The other option, of course, is to go the cheap route, such as signing J.T. Realmuto and Jorge Polanco, both with projected AAVs of about $15M. That also puts you right at $255M. Is that route easier for Breslow to execute? Of course it is, but you get players nowhere near the caliber of the top free agents. Alonso, Bichette, and Ryan move the needle into championship territory, Realmuto and Polanco do not.
There was a time when John Henry wanted to win championships. There are probably many reasons why that has changed, but it has changed. That’s for certain. Big market teams should have big market payrolls. The Dodgers, Mets, Yankees, Phillies, and Blue Jays have owners that want to win and executives who can build winners. It’s time for the Red Sox to step up to the plate and once again act like a big market team.