How to Fix The Red Sox Is Obvious But I Have No Faith In The Front Office Or Ownership To Get It Right

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I can see already see it. And I already hate it. 

Ten years from now, April of 2036. Note that in this scenario, our AI overlords have not yet taken over…yet. So, April 2036, no AI overlords, and the Red Sox are hosting a pregame on-field ceremony at Fenway Park, welcoming back players to celebrate their record 15-game winning streak and 32-5 stretch during the 2026 regular season. 

Sellin' Sam Kennedy called that stretch "magical and historic" a few days ago. And I can envision team ownership and its front office ignoring this past season's massive failures and focusing on that run as we get further away from the wreckage. 

Hopefully, I'm still alive to mock the hell out of it. 

New York Yankees. Getty Images.

The Red Sox whimpered right out of the playoffs for a second straight season. The team whimpered. And the bats whimpered - as they did most of the season. 

The Sox hit 163 home runs, good for fifth-fewest (26th) in all of baseball. The team had a similar power outage at the end of 2025, when Craig Breslow said this in the days after the season: 

“It would be fair to look at some of those other teams to say that they hit the ball out of the park a little bit more than we do…It doesn’t really matter how you score, but in the postseason, a lot of runs come via the home run because the pitching is so dominant. So I think that’s a consideration.”

So how is it possible to say those were words, acknowledge the issue, and then hit 23 fewer home runs the following season, after Breslow stated the obvious about the importance of home runs? 

Well, easy: They didn't want to spend the money. 

On Alex Bregman. On Pete Alonso. On what it would have cost in prospects to trade for Isaac Paredes. They just didn't have the stomach to pay top dollar for power. Instead, they pivoted to pitching and Ranger Suárez. In fact, they gave him $130 million and then never got a chance to pitch him in the postseason. 

That failure and Breslow's miscalculation led to the 2-game flameout in New York. Seems pretty simple in retrospect. 

It's doubtful we have a full season of baseball next year. A lockout looms, and no one seems confident the players (and their Union) and the owners will reach an agreement anytime in early 2027. We might have A LOT of time to talk about the next Red Sox game. 

So with that being said, there are four things that I keep thinking about in the aftermath of the season coming to a sudden end in the Bronx. 

Elsa. Getty Images.

Power

Duh. There was a time the Red Sox had legit power bats. Stars with power bats. Breslow ADMITTED the team needed to hit more bombs after last season, so my confidence level in the team actually investing in this area is low. Very low. Especially after this terrible answer the other day. 

Unreal. I mean, he's really sitting there citing Caleb Durbin setting a career-high in home runs when he went from 11 to 13, AND he played in 17 MORE games. His OPS and SLG were actually down from last season. And oh yeah, he had to go to an outside hitting specialist to get right early in the season. Sick stuff, Craiggers. 

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Owner John Henry is BEGGING for a salary cap, so we can stop pointing out that he spends less than he used to and treats the big-market Red Sox like the small-market Rays. His lack of spending is a big reason I have no confidence this gets better next season…whenever that is. 

Zero faith they spend money. Or make power a priority. Sounds like they'll just hope to get healthy. Maybe they'll make a trade. I don't know. It sucks because it's such an obvious need, and they'll so obviously fuck it up, as they did a year ago. Sweet. 

Winslow Townson. Getty Images.

Roman Anthony 

Just have to get him 100%. No excuses. Clearly, he was not healthy when he came back in September 

What a lost season for Roman. I know the Sox are saying no surgery, but if there's a chance he can be healed up better by going under the knife, then do it, right? Rest didn't seem to help in a season when he lost four months to injury and then had to bail out of a playoff series. 

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This hand thing turning into a chronic issue would be a disaster for the team and Anthony. 

Brian Fluharty. Getty Images.

Trevor Story 

Story is owed $25 million in 2027, and that should not be a reason to guarantee him a starting shortstop position - or a position on the team. 

Atrocious stuff here. He was injured, but it was just a terrible season for Story. He'll be 34 next season, and it's hard to point to anything he really does well. That salary should not lock him to anything, and if the team has to eat it get better, then so be it. Franklin Arias is the next uber prospect, and he plays short. I don't want to live in a world where he's at AAA, and the Sox are giving real at-bats to Story because he's the veteran. Nope. Or worse, because he's owed $25 million. Eating money to get him off the roster feels like the best move. 

The best version of the 2027 Red Sox does not involve Trevor Story playing a prominent role. 

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Align the Front Office and the Clubhouse

I loved Contreras basically saying you need players, not data, to win playoff games. There is nothing good about him having to have a two-hour meeting with the manager and Breslow. I feel like the team and the media took this as a good thing. 

Giphy Images.

There is a clear disconnect between Breslow's penthouse office and the clubhouse. It's been suggested he needs a translator to talk to some people in the organization - my guess is that includes the players. Which is crazy because he's a former player himself! 

Sean McAdam used the word "disrespected" when talking about how Sonny Gray and his teammates felt about his early Game 2 hook. There's little doubt that's aimed at a front office most people think is driving the direction of much of a franchise. Like, that can't linger into next season. 

Because, bigger picture, you need to make sure free agents want to play here. Between this, the Rafael Devers Trade, the Alex Bregman debacle…I can see how an opposing player might view Breslow and Co. as supremely unlikeable nerds who care more about spreadsheets than baseball games. 

Those feel like the Big Four, at least right now, after another playoff loss to the Yankees… who, by the way, just got swept out by the Rays. Shit, that makes it worse. Like, how bad were the Sox? 

We talked about a lot more on Episode 73 - Dirty Water - A Boston Sports Podcast. Go watch and subscribe on YouTube. 

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