The offseason is underway for the Boston Red Sox after the team was eliminated by the New York Yankees in an American League Wild Card series. Boston dropped the best-of-three matchup to New York, 2-1.
It was the first playoff appearance for the Red Sox since 2021. They held a year-end press conference Monday morning at Fenway Park that included club president and chief executive officer Sam Kennedy, chief baseball officer Craig Breslow and manager Alex Cora.
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What are Boston’s priorities as they build for 2026? Where do they need to strengthen for a run deeper into October? Providence Journal sports writers Bill Koch and Jacob Rousseau broke that down during an extended conversation.
(The following has been edited for grammar, clarity and overall polish. Two fans talking about baseball tends to invite tangents and the occasional extended rant. Nobody needs to see those in their entirety here.)
Grade this year’s Red Sox
Bill Koch: The Red Sox had their year-end press conference Monday. We’re going to hit on a few themes that will be important going into the offseason. We had Sam Kennedy, Craig Breslow and Alex Cora at the podium. Jake, let’s start with Breslow — his second year as chief baseball officer. If you had to give two or three main thoughts or a letter grade, how would you evaluate him?
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Jacob Rousseau: I think his wins were really significant in Year 2. But they were matched by some significant losses. Trading for and extending Garrett Crochet is immense. Putting him at the top of the rotation, that’s his marquee acquisition for his entire tenure in Boston — however long that is. Fleecing the Yankees for Carlos Narvaez —that looks like a guy who can backstop Boston for a long time. And you can’t overlook extending Roman Anthony (eight years, $130 million through 2033). He doesn’t get credit for drafting him or his development but he certainly gets credit for extending him early.
Garrett Crochet proved to be the most important addition to the Boston Red Sox this season.
His losses may have undone Boston’s season. Trading Rafael Devers was indefensible. Boston’s offense in the Wild Card series was anemic. The return — Jordan Hicks, Kyle Harrison and two prospects — were all irrelevant. Harrison was the only one who made the playoff roster.
BK: They thought so highly of Harrison that they pitched Connelly Early in Game 3.
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JR: Right. So, if I had to put a grade on it, I think he’s somewhere in the middle. Is a C fair?
BK: Normally I’m not the grade inflator, but I might have gone a little higher. Not much higher — C+ or B- for me. The Crochet deal is one the Red Sox should always be looking to make. Bringing in Alex Bregman gave them some presence. And then Aroldis Chapman had a really good bounce-back season. He was outstanding through 2025.
The major downside, of course, was the Devers trade. The front office helped create that. They signed Bregman in free agency and Devers felt blindsided. Did he act like a 5-year-old throughout the whole thing? Should he have been willing to play first base or designated hitter? You would hope so, yes. But the fact is they created a mess with their highest-paid player and they had to trade him for pennies on the dollar.
If Harrison is a star by 2027 or 2028, a No. 2 or No. 3 starter, great. But for now, you really hamstrung your team in the short term.
Trading away Rafael Devers to San Francisco was a blow to Boston’s offense that they did not recover from in 2025.
Offseason possibilities
BK: A couple of interesting decisions this offseason in terms of opt-outs — Bregman has one and Trevor Story has one. I fully expect Bregman to opt out. I know people say he’s not going to get $40 million AAV [average annual value] from somewhere else, and the counter to that is he’s going to get more than $80 million guaranteed. And that’s what he’s looking to do.
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JR: Let me just throw a name at you as a reference point — Matt Chapman. He signed an extension with the Giants that was six years, $151 million, and they’re about the same age. Is that the starting point there?
BK: That would be $25 million a year, but $70 million in new money.
JR: I kind of think it would start there for Boston. And I would have no problem giving Bregman that money.
BK: You certainly should have the payroll flexibility to do it. You just dumped Devers and $250 million on the Giants, right?
JR: How far am I willing to go? He can essentially write his own contract within some sort of limits. What he brings in terms of leadership, never mind his on-field production, can’t be understated. Boston, after losing Xander Bogaerts, definitely needed someone with his presence in that clubhouse.
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BK: Another interesting opt-out — Story. Honestly, if he opts out, I don’t think that’s the worst thing in the world for the Red Sox.
JR: I’m on the opposite side. For a team that led the league in errors — they were legitimately worse than the Colorado Rockies — it would be a negative to see Story opt out. If they can find a way to come to terms on a new deal that would lower his [annual average value] and repurpose that money. … I just can’t keep having talented baseball players leave this team, and especially one who solidified the left side of your defense at a premier position.
Red Sox shortstop Trevor Story had his best season in Boston this year.
BK: Story had his best season with the Red Sox, no question. He played decent defense on the left side with the exception of the throwing yips that showed up in September — that was a little scary. I look at his OPS+ and it’s 104, which means he’s barely above league average (100). The slash line isn’t great — .741 OPS, 33 walks, 176 strikeouts. That is an extreme ratio.
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I don’t know if you have other preferences like trying Marcelo Mayer there full time. One name that I’d really like them to explore, and this is a bit of homer bias, I admit, would be if the Astros are trying to retool a little bit. Jeremy Peña has two arbitration years left. If Houston isn’t willing to extend him, I’d be looking to give them a call.
JR: I think unfortunately, despite making the playoffs this year, they have a lot of holes. And creating more holes by seeing Story walk would not be helpful. I think Breslow has his work cut out for him. If you can leave Story at shortstop or second base, somewhere in the middle of the infield, I would prefer that.
Will Kristian Campbell become a regular next season for the Red Sox, after a disappointing 2025?
What will next season’s outfield look like?
JR: You asked me earlier about Kristian Campbell. Obviously, I don’t have much in terms of expectations. But if Jarren Duran and Wilyer Abreu move on for pitching or a slugger, does the outfield look like this left to right — Campbell, Ceddanne Rafaela, Roman Anthony?
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BK: Interesting. If you trade both of them, then yes, I think Anthony is your right fielder. If you trade Duran and Abreu is still here, I think Anthony is your left fielder and you just let him focus on his offense. The postseason probably would have looked different if he was in this lineup. You would expect him to grow into his power a little bit. But in terms of his at-bats, that’s the part your most excited about — the fact that he’s so mature for a 21-year-old.
JR: There might not be somebody in Boston who benefits more from the ABS [automated ball-strike] system than Anthony next year. He just looks polished at 21 years old and knows the strike zone — maybe Bregman knows it better. But Anthony is going to benefit so much from that.
BK: He’s obviously an everyday player and an everyday outfielder. You don’t diminish his development and his value by making him a DH.
I think you’ll see Anthony in left field. If you trade Duran, you’ll probably see Abreu in right field with Campbell maybe getting some at-bats playing left field and shifting Anthony into right. That could be your four-man outfield mix unless the Red Sox decide to really get aggressive in free agency and bring in someone like a Kyle Tucker.
Roman Anthony’s eye for the strike zone is impressive for any player, let alone a rookie.
JR: He still hasn’t agreed with the Cubs. His market is going to be strong. That would be quite the acquisition.
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Big-name free agents available
BK: You’ve got some free agents out there who would move the needle. Among the position players, you’ve got Tucker, Cody Bellinger, Pete Alonso. If Story opts out, do you get into the Bo Bichette sweepstakes? Is that somebody you try to take a look at? He knows the division. He would know Boston — Dante Bichette [his father] was here in the 2000s.
JR: I assume you’re locked in on adding a No. 2 starter?
BK: Yes. I need a starter who’s closer to Crochet. If you look at the Yankees, they signed Max Fried — he goes right to the top of the rotation. Carlos Rodon had a really good year. Gerrit Cole misses the entire year after Tommy John surgery and they’re still competing for the division. Then a guy like Cam Schlittler comes out of nowhere and is able to bridge the gap while Cole is hurt and Luis Gil is a nonfactor.
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JR: The other need for me is a backup catcher. Narvaez was really good but he wore down. It was by far the most games he’s ever caught. He’s going to have a procedure on his meniscus. You could tell the season wore on him and Connor Wong didn’t have much of an impact. Getting a backup catcher is important.
BK: Wong had a 42 OPS+ this year.
JR: It wasn’t good.
Triston Casas is taken off of the field on a stretcher after a collision at first base during the May 2 game against Minnesota. The injury ended his season.
Injuries took their toll
BK: This team has a fair number of guys who were hurt or got hurt this year — Triston Casas [knee], Tanner Houck [elbow], Mayer [wrist], Kutter Crawford [knee, wrist]. Are you counting on any of these guys next year?
JR: Is it harsh if I say no? I don’t expect anything. I haven’t seen it long enough from Casas. Mayer hasn’t finished a pro season [since 2022]. You already mentioned Houck [who could miss all of 2026 after Tommy John surgery] and Crawford — when he was healthy — was fine at the back end of a rotation. They might have better options.
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BK: In a perfect world, I think you’ve surpassed him. And granted, not everyone is going to stay healthy. If you’re at a point where you’ve got Crochet, you trade for a real No. 2 and you’ve still got Brayan Bello, you’ve got to think Early, Harrison and Payton Tolle. If none of those guys get traded, who do you like more?
JR: I think Boston told you in Game 3, did they not?
BK: They had Early out there instead of Harrison or Tolle.
JR: Boston told you who they have the most faith in. Tolle has a great fastball but that’s all he has. Right now, he’s not ready. I don’t expect him to be on the Opening Day roster. He might start at Triple-A. They might need two pitchers, and one of them would be a No. 2. That’s a lot.
Will former Bishop Hendricken star Michael King, currently a free agent after a season with the San Diego Padres, be on Boston’s radar?
Which pitchers would be good fits in Boston?
BK: Certainly the Joe Ryan rumors will come back. Do you get involved with someone like Ranger Suarez in free agency, who had a really good year for the Phillies? Framber Valdez? Dylan Cease is another guy who they’ve been connected to in the past. The strikeout numbers are huge. The stuff is premium.
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JR: Can I throw a name out at you? What about Rhode Island’s own Michael King?
BK: Very interesting free agent. He was not healthy this year. He was not able to repeat the innings total that he gave the Padres in 2024. You wonder about his durability if you’re going to give him four or five years. But he has shown you at his best that he can be among the elite starters in the major leagues. He’s certainly no less than a No. 3 on a really good team.
JR: I would feel really good if the rotation starts with Crochet, fill in the blank at No. 2, King and then Bello. Early would probably round it out.
BK: That would be good. And you’d feel good about going into a playoff series with that group. King won two playoff games with San Diego in 2024, so he’s got good experience.
JR: They should just hire us, right?
This article originally appeared on The Providence Journal: Boston Red Sox offseason game plan and a report card on 2025