OTM’s Red Sox Offseason Predictions

Boston Red Sox Spring Training 2024 — Photo by Barry Chin/The Boston Globe via Getty Images

With the offseason gearing up, the OTM staff makes its predictions for the next four months of player movement.

One Bold Prediction

John Henry will actually show his face at Winter Weekend and speak with the fans.

Hey, you asked for bold, right?

With whispers within the baseball industry already indicating that the Red Sox will firmly be present in the kitchen working when the stove gets hot—and DraftKings’ lines reflecting that notion, for what it’s worth—I can’t help but thinking that there’s fire where we’re currently seeing some smoke.

Again, like I mentioned last week on this very website: maybe I’m setting myself up to be Charlie Brown running up to try and kick the football, but I’m optimistic that this off-season will be a productive one for our beloved ball club. The team is not burdened with a ton of bad money going forward and already appears to have many parts of a future core under team control for the foreseeable future.

Simply put: the team has the capacity to spend in free agency if they feel so inclined. If you believe Jen McCaffrey of The Athletic (which I do) and mega-agent Scott Boras in an interview with her (which I’m less inclined to do, admittedly, but the logic still checks out), the Red Sox brass plans to take advantage of that capacity.

“In our meetings, (the Red Sox) are definitely letting us know that ownership is committed, that they’re wanting to secure high-level players and that they’re definitely planning on being very active in the free agent market,” Boras was quoted as saying in The Athletic.

So let’s just assume that’s true for a moment. I know that you don’t want to assume because it only makes and ass out of u and me, but try it for a moment. Say the Sox go and spend on a Corbin Burnes, or a Max Fried, or a Teoscar Hernandez Say Boston takes a big swing and trades for a stud. Say this winter brings us right back into the mix, at least on paper.

John Henry’s gonna want to take advantage of that, right?

After getting a ton of shite for the last couple of years (and rightfully so) post-Mookie trade about being more concerned about other parts of the FSG portfolio and for checking out on Red Sox Nation, wouldn’t a slew of transactions that make big headlines provide Henry with an opportunity to tell the fans that he does, actually, care? Whether or not you’d buy that is another conversation—one I’m sure you’ll have below in the comments—but that would be the ideal chance to tell everyone that the Red Sox are back in business, no?

The excellent Netflix documentary on the ‘04 Sox showed that John Henry is more than willing to speak when it’s a positive topic; he’s not stupid. Whenever/wherever Winter Weekend is held this year, I think a notable slate of moves beforehand would give him the platform to say that he—much like the team he owns—is alive and well.

—Fitzy Mo Peña

The Red Sox will trade Marcelo Mayer.

The team fell ass-backward into Marcelo Mayer in the 2021 draft and has stuck with him through good and bad since then, but I think of all the Sox’s top prospects he’s the most tradable, so I’m suggesting they deal him this offseason in what I’d hope is a sell-high move. Giddyup.

In general I don’t think the Sox will be overly bold this offseason; one big-ish move ought to do it. But if there’s a prospect in the big-ish move, I think it’s Mayer. In fact, if I was in charge of making a big-ish move for the Sox, I would do what I could to shove Mayer off on another organization, should I get paid a premium for doing so, which I think is still a possibility. It’s not merely that he was the No. 4 overall pick; it’s that he’d have been No. 1 if not for contract concerns and some strange choices by teams ahead of the Sox that looked bad as soon as they made them. Such anchoring is hard to move past, and I suspect most of MLB hasn’t moved past it. I suspect, however, Craig Breslow has, and if he needs to make a move, Mayer is the expendable one. I’ll live.

— Bryan Joiner

The Red Sox will sign an Ace.

91st MLB All-Star Game presented by Mastercard

Craig Breslow is already back to the motto of “pitching, pitching, pitching” and there is only one way to realize this: get pitching. We know the path to “contention every year” is a strong farm system.

There is no other way to show that ownership wants to keep winning unless they add someone from outside the organization. The farm is strong. They can afford to lose a pick. The budget space is there. They can afford to spend.

From there: the upside is limitless.

— Mike Carlucci

The Red Sox will sign Teoscar Hernandez.
He got his ring on his prove-it deal, and put up the second-best WAR of his career, at 3.5, while hitting 33 home runs. With Tyler O’Neill’s future with the team all but written on the wall, the front office will need to replace his 31 home runs with a guy they actually trust to field, while keeping in mind the blooming Roman Anthony will likely be playing at Fenway in a year’s time. This goes in harsh juxtopisition with my boring prediction of the Red Sox not cashing out this offseason, but, in addition to some pitching depth (yes, I said depth… unfortunately…) Henry, Breslow and company will look to console the masses by picking up this 31-year-old All-Star, somewhere in the realm of 3 years/72 million dollars. After declining to extend a qualifying offer to O’Neill, will it feel like the Patriots picking up Juju Smith-Schuster and letting Jakobi Meyers walk to Las Vegas? Sure… but Hernandez coming off the best season of his career and having been some of the secret sauce to the Dodgers’ success will be much more rewarding.

— Dean Roussel

John Henry will commit more money in free agency this winter than he has in any winter in franchise history.

World Series - New York Yankees v Los Angeles Dodgers - Game 1

Part of this has to do with inflation. As the man once said “baseball players are expensive,” and like everything else, they’re only getting more expensive. This bar is going to be so much easier to clear than most people realize at first glance because prices are just so much more expensive than the last time the Sox truly invested in a free agent class. A Juan Soto contract alone would blow it out of the water; although I think the more likely path here is through a combination of pitching signings.

All of this though brings us to the more important point, which is that there’s a pretty decent chance John Henry decides to turn on the faucet and invest in this team sooner rather than later. While he’s certainly thrown his baseball team to the side in recent years and rightfully infuriated Red Sox fans, I don’t think he’s completely done with them. Henry has future real estate plans in the works around Fenway Park, and that project will be more successful if the Red Sox are acting like the Red Sox.

Also, Henry spent most of the last year amid major players in the PGA Tour vs. Saudi LIV Golf clash, and when that dust settles, he’s going to walk away with an ungodly sum of Saudi oil money to invest elsewhere in his other businesses.

— Matthew Gross

Boston will trade either Triston Casas or Jarren Duran for a top pitcher.

I know that there are rumors that the Red Sox could trade for Garrett Crochet without needing to include either Duran, Casas, or any of the big four prospects. I find that hard to believe. Front-line pitching is just too expensive, and a package headlined by Wilyer Abreu doesn’t feel like enough to me, even though Crochet only has two years remaining prior to free agency. You have to do something uncomfortable to trade for a true, capital-A Ace, something like trading your top two prospects (Yoan Moncada and Michael Kopech) for Chris Sale.

If it does require Casas, Duran, or one of the Big Four to return an Ace, I would rather Boston trade with Seattle than go after Crochet, who has had a significant history of arm injuries and just moved to the rotation from the bullpen in 2024 to throw 146 innings.

Triston Casas for George Kirby, Logan Gilbert, Bryce Miller, take your pick and then go sign a powerful right-handed bat. Or, perhaps a Wilyer Abreu-headlined deal could instead land the 32-year-old Luis Castillo. The Mariners can say they won’t move a pitcher for hitting but they have missed the playoffs in consecutive years after ending their 20-year playoff drought in 2022 thanks to an anemic lineup.

— Bob Osgood

Boston will sign one Scott Boras client WITHOUT any fuss.

This is less of an indictment on Red Sox management and more on Scott Boras. The most notorious agent for creating drama in the free agent market (look at Jordan Montgomery and Blake Snell last year) has an even larger swath of clients on the market ready for a big pay day. Juan Soto aside, there’s Corbin Burnes, Yusei Kikuchi, Pete Alonso, Alex Bregman, Blake Snell (again). On both the mound and in the box, there are some both tantalizing and risky options for Craig Breslow and company to take a look at. What should shock everyone is the lack of drama around the Red Sox signing one of these free agents when it happens.

— Jake Reiser

One Boring Prediction

Prices at Fenway Park will increase… again

John Henry’s gonna try to make his money. At the very least, maybe the justification for the annual price hike will be the improvements made to the team that plays 81 times at Fenway, right wrong or indifferent. Get ready to pay $2.50 more for those Sam Summers, buddy.

— Fitzy Mo Peña

The Red Sox will acquire a depth starter and Twitter will explode.

At some point over the next few weeks, the Red Sox will acquire a pitcher that few have ever heard of in a Cooper Criswell-style transaction. The general fanbase will be furious about the move because we’re all impatient and judge every move in a vacuum, rather than waiting to judge the offseason as a whole. The terms “dumpster diving” and “Chaim Bloom 2.0” will be used frequently. In April or May when a spot-start is needed, we’ll all be thankful for the 4.1-inning, three-run outing that helped reset the rotation and will repeat the same outrage at these signings the following offseason, having not learned our lesson.

— Jacob Roy

There won’t be enough infielders.

Injury or ineffectiveness, it doesn’t matter. They’ll enter, say, May, having used more starters at second base than any other position.

— Mike Carlucci

Juan Soto and Roki Sasaki will both sign with someone else, Red Sox fandom will be in turmoil.

As Dan outlined a few weeks ago, regardless of slightly less vague messaging around contending (the Red Sox plan to spend this offseason!), John Henry is cheaper than a team out of Boston should be, according to their Scrooge Index. By Christmas, the 23-year-old Japanese phenom pitcher will have signed with (insert playoff team willing to spend here) and the 26-year-old future Hall of Fame slugger will be on his way to his fourth team in as many years, but this one long-term. Neither of them will be the Red Sox, and Breslow and Sam Kennedy will have to explain themselves again. Of course, I’d love either of the two players on the roster as much as you, dear reader, but, simply put, this team will not spend upwards of $40 million dollars annually on one player.

— Dean Roussel

The NESN experience will not improve, even though it desperately needs an upgrade

There was time when cable was at its peak where the Red Sox day to day broadcast experience was among the best in all of baseball. Now, not only have most other teams moved ahead of that product, but the Red Sox have actually let it rot and become worse. With the collapsing cable industry, the uncertainty of which streaming services will survive, and the question marks surrounding MLB’s blackout policy going forward, I’d expect ownership to pass on investing in any upgrades here until the business picture becomes clearer.

However, if I’m right that the Red Sox actually invest in the product on the field, the cries to improve this horrific customer experience will grow louder.

— Matthew Gross

The Red Sox’ offer to Juan Soto will fall far short.

Just because they’re in the room doesn’t mean they’re serious about signing him. Ten years ago, I would’ve put the Red Sox chances at 30% to sign Soto and today I put it at 1%.

As MLB Trade Rumors outlined so well in their free agent predictions write-up on Soto (Spoiler Alert: he’s at the top of the page), Scott Boras will be looking to match or exceed the net present value on Ohtani’s contract, which is $43.7M per year because of the deferred money. If we round down, 13 years at $43 million is $559M. Do we have a single reason to think the Red Sox would be willing to make anyone an offer that starts with a 5? They weren’t willing to pay Mookie Betts, a homegrown talent, the 12 years and $365M (30.4 per) that it required to retain him and instead chose to tear down a championship squad for no reason. They haven’t been serious about signing a top free agent since David Price in 2015 and I won’t believe otherwise until I see it.

— Bob Osgood

The Red Sox will win the “we tried” award in the offseason.

Boston Red Sox end of season press conference

It’s already happening, with notable journalists and unnamed front office sources saying the Red Sox are “primed to spend” and “have the farm system to trade for anyone they want”. It won’t happen. As it does every year, the Red Sox will meet or be linked to every big name free agent under the sun and inevitably fall short. Hope for the best, prepare for the worst, right?

— Jake Reiser

The Red Sox will acquire none of Juan Soto, Garrett Crochet or Max Fried.

Duh.

— Bryan Joiner

When pitchers and catcher report the vibes will be. . .

Remarkably High.

I’m ready to be hurt again. While last year’s season was frustrating, I think you could see the bones of a good team. Weirdly, for whatever reason, I believe that the Red Sox will be aggressive this offseason to supplement the skeleton they have in place. I know, fool me twice shame on me, but the talk feels different this winter. I fully expect the Red Sox to go out and get an ace (Garrett Crochet), add to the team in other areas, and have sky-high vibes heading into Fort Myers. It’s gonna happen, I swear.

— Jacob Roy

Ask me again in a few months.

If the front office makes some power moves prior to reporting to Fenway South, the vibes will be through the roof. The Red Sox will officially be BACK, baby. If we see Full Throttle II: The Squeakquel, then it’ll be considerably less fun in Fort Myers. The youth movement will still be in full swing, which is nice, but I think we’ll be resigning ourselves to another bridge year.

— Fitzy Mo Peña

Unrealistically optimistic (complimentary).

I expect the Sox to be objectively more aggressive this offseason, albeit more by inches than miles. I think they’ll try just a tad harder and that will be that. To that end, I think they’ll be better next year, and because of that we’ll look on the bright side of it all. Who could blame us?

— Bryan Joiner

Cautiously Optimistic.

2024 Boston Red Sox Rookie Development Workout

The 2024 Red Sox won 81 games. Jarren Duran is coming off a career year. Ditto Tanner Houck. The Big Four are progressing through the farm system. It’s not “playoffs or bust” but the Wild Card is very attainable. Very. This is finally the year to step forward.

But I do have a caveat on this: they need to make moves this winter. Sign Blake Snell or Corbin Burnes. Or both! Trade for someone. Don’t roll out the ‘24 team again. For all its problems and successes that team needed help and Craig Breslow fell short.

— Mike Carlucci

Pressure-filled.

In the first half 2024 the Boston Red Sox showed they have some of the pieces already to be true contenders. In the second half of 2024 the Boston Red Sox emptied the gas tank for nothing and exposed where the major flaws still live. Breslow knows he has to get this team to play a solid 162 games to get to the playoffs. I don’t know if Red Sox Nation cares enough right now to have World Series hopes, I think we just want to see them contend for October baseball in general! In year two of the Breslow tenure, he has to show the willingness to improve the club he talked about when he was hired last year. Regardless of what ends up getting done or not, the pressure is on. Playoffs or bust.

— Jake Reiser

Excited About the Future.

Kristian Campbell. Marcelo Mayer. Roman Anthony. Kyle Teel. Chase Meidroth. Jhonstynxon Garcia. Richard Fitts. Wikelman Gonzalez. Elmer Rodriguez-Cruz. Jedixson Paez. These are all guys likely to spend some time at JetBlue Park in Fort Myers this March, and it will give a lot of fans, myself included, loads of enthusiasm for 2026, 2027, and beyond. Now, I’ve said it a few times already this offseason, and I’ll say it again: if guys not ready to play at a Major League level are the only reasons Fenway faithful have to be excited in 2025, it will signify a failure of an offseason. But, at the very least, a system that gets criticized for not moving enough of their prospect depth for valuable pieces of the present will garner plenty of attention in Florida, especially with quite a few finishing 2024 on meteoric trajectories.

— Dean Roussel

Cathartic.

Life is a struggle for far too many people right now, and unfortunately, most of the pervasive problems that plague us as a society are only going to get worse. But for Red Sox fans, there is a silver lining. Our baseball team might be on the verge of getting good again. Really good!

Right now, they have prospects and the room to spend, which if they’re serious about winning at all is usually a precursor to run of successful baseball that can last a half decade or more. There’s just something that makes life a little bit easier when, amidst all the real world carnage, you can sit down every evening for a couple of hours and escape into the wondrous world of a competitive baseball team. One small taste of the good stuff and most of the region will quickly realize how much they’ve missed having the Red Sox in their lives. In a world of awful, this will feel so, so satisfying!

— Matthew Gross

The best they’ve been since 2019.

I’m not certain the team will, finally, spend beyond the $241 million Competitive Balance Tax, but it wouldn’t shock me. Offering Nick Pivetta a qualifying offer of $21.1M is not something you would do if you’re trying to totally pinch pennies this offseason. The Big Four will be at Spring Training, at least one of them will knock the door down to make the Opening Day roster, and I expect that they’ll all be up at some point in 2025 and I expect that a couple of strong veteran free agents are brought in this offseason to build around them.

The last five years have collectively sucked, but it’s Go Time.

— Bob Osgood