Monday marks the real start of the MLB offseason as option decisions are due, free agents can technically start signing anywhere and general managers across the league will all travel to San Antonio for the start of the annual GM meetings. So begins what should be a very busy winter for the Red Sox and chief baseball officer Craig Breslow.

It’s clear Boston’s roster will look much different on Opening Day compared to now. But just exactly what will Breslow and the Red Sox do? Here are some bold offseason predictions from our Red Sox writers, Chris Cotillo, Sean McAdam and Chris Smith.

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1. The most expensive free agent the Red Sox will sign this winter is:

COTILLO: Teoscar Hernández

Once the Red Sox acquired Tyler O’Neill from the Cardinals last winter, Hernández didn’t make much sense for the roster. Now, he does. He’s an upgrade over O’Neill and would be a perfect fit to add to a lefty-heavy outfield mix, especially if Boston can somehow move on from Masataka Yoshida and open up some DH at-bats as well. Hernández is probably looking for a bit of stability after signing a one-year pillow deal with the Dodgers and has made it clear he’d love to play in Boston, where he has always raked. The Athletic’s three-year, $75 million projection for him seems fair.

MCADAM: Tanner Scott

The free agent starting rotation market will prove to be too expensive, so the Red Sox pour their resources into a power lefty arm to upgrade their bullpen.

SMITH: Tanner Scott

The Red Sox will load up on relievers and make their bullpen a major strength. The hard-throwing Scott posted a 1.75 ERA in 72 outings for the Marlins and Padres this past season.

2. Boston’s Opening Day rotation will consist of:

COTILLO: Garrett Crochet, Tanner Houck, Jack Flaherty, Brayan Bello, Lucas Giolito

The Red Sox need an ace who they can keep for a while and Crochet, who is almost a lock to be traded this winter, is an ideal fit. A mid-rotation free agent addition like Flaherty or Sean Manaea makes a lot of sense, too. Note that Kutter Crawford isn’t part of the group. More on that in a minute.

MCADAM: Garrett Crochet, Lucas Giolito, Brayan Bello, Tanner Houck, Kutter Crawford

The Sox trade for Crochet, giving them a lefty and a front-of-the-rotation starter with several years of control.

SMITH: Tanner Houck, Brayan Bello, Kutter Crawford, Lucas Giolito, Bryan Woo (OR another trade acquisition)

Seattle starter Bryan Woo makes a lot of sense as a potential trade addition. Mariners president of baseball operations Jerry Dipoto has said he does not plan to trade any of his starting pitchers. But Dipoto has an abundance of pitching he could use to upgrade his offense.

The Mariners were 25th in the majors in slugging percentage (.376) and slugged just .404 from the first base position last year. Perhaps they will listen if the Red Sox offer Jarren Duran or Triston Casas.

3. The most significant trade addition Craig Breslow makes this winter will be:

COTILLO: Garrett Crochet (White Sox)

The Red Sox turned to the White Sox when they needed a left-handed ace to put them over the edge eight years ago. Why not do it again now? Crochet is 25 and has a ton of upside even if he doesn’t have a long track record of success in the big leagues. He’s controllable through 2026 but is a prime extension candidate; the Red Sox would likely want to talk to him about a long-term deal before pulling the trigger on a deal.

MCADAM: Garrett Crochet (White Sox)

The Sox checked in on Crochet at the deadline, but Crochet’s comments about not pitching in the postseason without a contract extension made dealing him impossible. Without that complication, they find their elite starter in the offseason.

SMITH: Bryan Woo (Mariners)

As mentioned above, starter Bryan Woo from the Mariners would be a good fit. It feels likely the Red Sox will trade for a starting pitcher — whether it be White Sox‘ Garrett Crochet, Marlins’ Jesús Luzardo or a member of the Mariners staff like Woo.

4. The best Red Sox player or prospect traded will be:

COTILLO: Wilyer Abreu and Kutter Crawford

For years, the Sox’ organizational white whale has been a trade for a major big-league addition that didn’t include any of the “Big Three” of Roman Anthony, Marcelo Mayer and Kyle Teel. Now, they’re trying to keep those guys and Kristian Campbell, whose amazing 2024 made him a top prospect. There’s a way to do that, and it’s moving major league pieces for someone like Crochet. A package of Abreu and Crawford (two somewhat proven major league contributors) plus a couple lower-level prospects could entice the White Sox as they try to accelerate their rebuild.

MCADAM: Triston Casas

Casas is sent to the White Sox as part of the package to acquire Crochet.

SMITH: Triston Casas

Again, Seattle has said it doesn’t plan on trading any of its starting pitchers. But maybe they’ll listen if the Red Sox offer a slugger with 40-homer potential who is under team control through 2028.

5. Coming out of spring training, the Sox’ closer will be:

COTILLO: Justin Slaten

Slaten has the pitch mix and the makeup to close. There’s no reason to think he can’t meet the challenge after an outstanding rookie year in 2024. That the Red Sox will have Liam Hendriks on the roster is something of a bonus but it’s hard to count on Hendriks after a long road back from Tommy John surgery. I’m also going to predict that they make a strong run at top reliever Tanner Scott or add some other high-octane lefty to the mix. But Slaten is the likely Opening Day closer for now.

MCADAM: Tanner Scott

The Red Sox will also have Liam Hendriks as a back-end option, but Scott will get the ninth inning.

SMITH: Justin Slaten

I expect the Red Sox to add a hard-throwing reliever like Tanner Scott to pair with Liam Hendriks in the setup role. Slaten enjoyed a strong rookie season in 2024, posting a 2.93 ERA, 1.01 WHIP and 13 holds. He had excellent command, averaging 9.4 strikeouts and 1.5 walks per nine innings.

6. Tyler O’Neill and Nick Pivetta will sign with:

COTILLO: Mariners (O’Neill) and Rays (Pivetta)

O’Neill has a much better chance to return to the Red Sox than Pivetta, who appears to have little chance of re-signing. Seattle needs offense and could get a spark from O’Neill, a British Columbia native who grew up as a Seattle fan. The Rays have been enamored with Pivetta forever and will want to get him in their pitching lab. Not hard to imagine him being a thorn in Boston’s side for a couple years in the division.

MCADAM: Blue Jays (O’Neill) and Astros (Pivetta)

O’Neill signs with Toronto and gets to play in his native Canada. Pivetta goes to Houston, which has coveted him for some time.

SMITH: Red Sox (O’Neill) and Astros (Pivetta)

O’Neill re-signs with the Red Sox and Pivetta inks a deal with the Astros. Houston had interest in acquiring Pivetta at the trade deadline but the Red Sox decided to buy, not sell. O’Neill enjoyed his season in Boston and he’ll be in their price range.

7. An outside-the-box move Craig Breslow will make is:

COTILLO: Shopping Masataka Yoshida in a salary swap — or trading him for pennies on the dollar

Yoshida isn’t without value as he truly was an elite bat-to-ball offensive player against righties for a huge portion of last season. But the Red Sox’ roster fits much better without him. Breslow will likely do everything he can to offload Yoshida, who is even harder to trade now that he’s recovering from shoulder surgery. What about a bad contract swap with Arizona involving Jordan Montgomery?

MCADAM: Sign Japanese first baseman Kazuma Okamoto

Okamoto would replace Casas at first and give the Red Sox a righty power bat to help balance out the lineup.

SMITH: Move around significant pieces to acquire St. Louis’ Nolan Arenado

It certainly would be bold if Breslow traded Triston Casas, moved Rafael Devers to first base and traded for Cardinals third baseman Nolan Arenado who would vastly improve the infield defense alongside his former Rockies teammate, shortstop Trevor Story. Arenado also would provide another right-handed hitter in a lineup that struggled against lefties last year.

8. Of their own eight free agents, the Red Sox will re-sign:

COTILLO: Danny Jansen

Nick Pivetta and Kenley Jansen are goners and Tyler O’Neill won’t return if Teoscar Hernández is signed. So there aren’t many likely reunions. The Sox do need a backup catcher though and could do worse than Jansen, who has familiarity with the pitching staff and a bat they think can play at Fenway. Even as a holdover before Kyle Teel debuts, Jansen fits on a cheap deal.

MCADAM: Chris Martin

There’s not much else to interest the Red Sox on this list, but Martin, who has said he’s likely to retire after 2025, likes Boston enough to return for another season.

SMITH: Tyler O’Neill and maybe Chris Martin

Martin said he wants to pitch for one more year and then retire after the 2025 season. He’s open to re-signing with Boston after posting a 2.16 ERA in 100 outings for them the past two seasons. He walked just 11 batters in 95 ⅔ innings.

9. The young player most likely to sign an extension with the Red Sox this winter is:

COTILLO: Roman Anthony

“Likely” might not be the right word here. So no need to aggregate, Milliken. But the Red Sox want to make an effort to lock up the players they think are future stars before they even reach the majors and Anthony should be a top target. A Triston Casas extension isn’t likely this winter after an injury-plagued year. Boston has never seemed to look at a Jarren Duran deal as a priority. And if I’m trading Wilyer Abreu and Kutter Crawford, then an Anthony push makes sense.

MCADAM: Jarren Duran

Duran is a foundational piece around which the Red Sox can build. After extending Ceddanne Rafaela and Brayan Bello, the Sox focus in on — and secure — Duran.

SMITH: Tanner Houck

Houck was Boston’s ace in 2024 (3.12 ERA, 30 starts). MLBTradeRumors projects him to earn $4.5 million in 2025, his first year of arbitration eligibility. He’s under team control through 2027. The Red Sox should offer him a six-year deal, buying out his arbitration years and adding three more years of him under team control. A significant raise in 2024 could motivate Houck to sign an extension.

10. Juan Soto will sign with:

COTILLO: Blue Jays

It’s no fun to guess the Yankees or Mets, who are the favorites. Toronto made a major bid for Shohei Ohtani a year ago and seems determined to add a superstar. The Jays have the payroll to do that, too. Don’t be surprised if the AL East is even more loaded come Opening Day.

MCADAM: Mets

Steve Cohen goes dollar-for-dollar with the crosstown Yankees and won’t take no for an answer. Scott Boras clients always go to the highest bidder and the Mets win the war.

SMITH: Yankees

New York traded five players, including Michael King and a top 100 prospect, to the Padres to get Soto last offseason. He can’t be one-and-done with the Yankees. They need to lock him up. There was no way the Dodgers were going to let Mookie Betts walk after acquiring him from the Red Sox in 2020. This is the same situation — although L.A. never let Betts get to free agency.

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