What Would a Fire Sale Look Like?
And who should be the one to direct it?
The Red Sox are now 23-33, 10 games under .500 after playing 56 games, just past the one third mark of the season. Yes, there are 106 games to go and as Kevin Garnett would say “Anything is Possible!” but let’s face it, things aren’t looking good. To win 85 games, a probable minimum for a playoff berth, they would need to go 62-44 the rest of the way, 18 games over .500 and a .585 winning percentage.
At some point, typically in early July, teams decide whether they are going to be buyers or sellers. What does that mean? Teams who think they are in contention for a playoff spot will look to add players who will help their chances. Teams who think they won’t be in contention for a playoff spot will look to offload their good players with expiring contracts. Why? Because they are ideal low risk candidates for the acquiring team and could possibly bring back young major leaguers or minor league prospects to help the selling team the following year.
This year is a bit different. The players’ current collective bargaining agreement (CBA) is expiring at the end of the season and the opening salvos in the negotiation of the next one have been fired. By all accounts, this will be the most contentious negotiations since the 1994 season, when the players went on strike in August and the World Series had to be cancelled. One of the main issues, a salary cap, was the cause of that strike and this will be the main issue in this year’s negotiations as well.
The way this plays into the trade deadline is that if there is a strike or lockout in 2027, the players will probably not get paid for however long the work stoppage lasts. This may cause a team to trade for a player who has a deal through 2027, gambling that they won’t have to pay him.
So, for now let’s assume things don’t get better for the Red Sox and they want to trade away their expiring contracts and bring back as many good young players as they possibly can. Who are the biggest trade candidates? Here is a list of some players that could be used as trade chips at the 2026 deadline:
While it is possible that the Red Sox might try to move players with long term deals, it is unlikely. Garrett Crochet and Ranger Suarez are owed a lot of money and not many teams may want to take that on. Here are the players that I think will be the hottest commodities at the deadline:
Aroldis Chapman
He is in his second season of being one of the best closers in baseball. Teams will probably be killing each other to get in the mix for him. They will only need to pay about one third of his $12M salary for 2026, and even though he has a vesting option in 2027, that season may not even happen. Watch for him to be a prime trading piece in July.
Willson Contreras
Contreras’ contract runs through 2027 with a club option for 2028. He has had a terrific year for the Red Sox and would be a great bat for a contending club. While his contract is not expiring, he is a player that a team would want to have for 2027 or take the chance that there is a work stoppage.
Sonny Gray
He has had a pretty good season so far for the Red Sox and is exactly the kind of starter that a team would want to a playoff run. They would only have to pay about one third of his $35M salary and his contract expires at the end of the season. This is the type of player that can command a very good haul at the deadline.
Jarren Duran
He is starting to heat up at the plate, and his glove has been good this year. He still has two more years of arbitration after this year, and this is very desirable for an acquiring club. His temperament may be an issue, but his speed is not. I think he will warrant some interest and possibly bring back some good prospects.
Garrett Whitlock
Whitlock has been an excellent back of the bullpen reliever for the Red Sox and has a very team friendly deal, with two club options in 2027 and 2028. He could be a key setup man for a team’s playoff run, and possibly a closer in a pinch. He’s that good.
What about the Albatrosses?
Of course, I’m talking about Trevor Story and Masataka Yoshida. Story will probably be out until after the trade deadline so forget about that. Yoshida is a replacement level left-handed bat that might warrant some interest, but he’s owed $18M in 2027 which most teams wouldn’t want. I think the Red Sox are stuck with these two.
What about the Kids?
Brayan Bello, Roman Anthony, Kristian Campbell, and Ceddanne Rafaela could certainly warrant some interest from other teams, but their long-term contracts are probably not desirable. Rafaela is really the only one who has proven himself to be a valuable piece in the majors. There are also a bevy of controllable players that might be desired by other teams: Marcelo Mayer, Wilyer Abreu, Connelly Early, Payton Tolle, and Justin Slaten to name a few. Would the Red Sox be willing to part with any of these players if the return is right? They’d better be.
Who should be making the deals?
Here at the Fire Breslow Podcast, we are counting the days until Craig Breslow is, well, fired. I think this is now a forgone conclusion. The question is when. Once John Henry and Sam Kennedy get it through their thick skulls that this is a lost season, they should pull the trigger. Ideally this would be no later than late June so the front office can start preparing for trade negotiations. That’s fine, but who will be making the deals?
Let’s have a look at the current Executive Management Team under Craig Breslow:
Brian O’Halloran – Executive VP of Baseball Operations
O’Halloran was with the Padres under Larry Lucchino who brought him to the Red Sox. He rose through the ranks over the years and is now the top executive under Breslow. He was briefly the General Manager under Chaim Bloom but was renamed as an EVP when Bloom was fired.
Raquel Ferreira - Executive VP & Assistant GM
Ferreira was first hired by the Red Sox in 1999 as an administrative assistant. Theo Epstein made her Director of Minor League Administration in 2004. In 2019 after the Dombrowski firing, she became one of the interim front office leaders than managed the team until the Chaim Bloom hiring. In December of 2019 she was made an assistant general manager.
Eddie Romero - Executive VP & Assistant GM
Eddie started his career with the Red Sox in 2006 as an assistant in international scouting. His father played for the Red Sox from 1986-89. He was promoted to his current role in 2018. He has a background in both minor league and professional scouting, which makes him an interesting candidate for interim GM.
Michael Groopman & Taylor Smith - Senior VPs & AGMs
These two are lower level executives and are probably not candidates to fill an interim GM position.
I think it is clear that Brian O’Halloran would be the obvious choice to be an interim GM and carry out any trade negotiations. Ferreira has been mostly on the administrative side and seems not to have scouting experience, but she may be valuable from a contract negotiation standpoint. Romero’s experience may be very valuable from a talent evaluation perspective. So, this could be an executive trio with O’Halloran at the top. Between the three of them, they may be effective at bringing back valuable assets, but I won’t get my hopes up. This front office consistently finds ways to underwhelm.
The other option is hiring from the outside, but seriously who would want a job under Sam Kennedy that will probably last only 3 months? The Red Sox are toast for 2026, but they might still be able to salvage the season by building for the future. Red Sox Nation prays that John Henry makes the right decision to fire Craig Breslow early enough to allow his front office to prepare for the trade deadline.