Monday marks the start of the baseball offseason as option decisions are due, free agents can technically start signing anywhere and general managers across the league will all travel to Scottsdale, Arizona, for the start of the annual GM meetings. And so begins what should be a very busy hot stove season for the Red Sox and new 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 Breslow and the Sox do? Here are some offseason predictions from our Red Sox writers, Chris Cotillo, Sean McAdam and Chris Smith.
1. The most expensive free agent the Red Sox sign this winter is:
COTILLO: Aaron Nola.
The Sox are going to be linked to virtually every top free agent starter this winter, including Yoshinobu Yamamoto, who will likely command about $200 million. The guess here is that they’ll be outbid and pivot to an innings-eater like Nola, who has a proven track record in a big market and will be cheaper. Nola, however, won’t be Boston’s most impactful rotation addition.
MCADAM: Yoshinobu Yamamoto.
The Red Sox need a front-of-the-rotation starter and Yamamoto is not only the best option, but also the youngest. For a team whose owner has been reluctant to give long-term deals to pitchers already in their 30s, that could be key.
SMITH: Yoshinobu Yamamoto.
The Red Sox’s biggest need this offseason is starting pitcher. Who better to land than the top pitcher on the market (not named Shohei Ohtani)? That would be “full throttle” as chairman Tom Werner suggested would be Boston’s offseason approach.
2. Boston’s Opening Day rotation will be comprised of:
COTILLO: Aaron Nola, George Kirby, Brayan Bello, Chris Sale, Lucas Giolito.
House money is on the Red Sox adding two starting pitchers this winter. Why not three? Nola and Giolito are two intriguing free agent arms the Red Sox will likely explore adding. But Breslow should look to Seattle to see if he can pry one of the Mariners’ young starters (like George Kirby or Logan Gilbert) in a blockbuster trade. Kirby, who is under control through 2028, is a perfect fit but would cost a mint. Let’s project Kutter Crawford is one of the pieces going the other way in that deal. Sale can’t be counted on due to the health risks but still showed his ceiling at points last year. Nick Pivetta is a depth option who might take the hybrid role, but don’t count him out as a sneaky trade candidate. It’s time for Garrett Whitlock and Tanner Houck to go to the bullpen permanently.
MCADAM: Yoshinobu Yamamoto, Jordan Montgomery, Brayan Bello, Chris Sale, Kutter Crawford.
Bello could use some support in the front of the rotation as he grows into his role, and in addition to Yamamoto, Montgomery is an intriguing pick. He’s left-handed, and because he was traded in the middle of last season, he can’t be given a qualifying offer, meaning he won’t cost a draft pick. Sale and Crawford round out the back end.
SMITH: Yoshinobu Yamamoto, Brayan Bello, Kutter Crawford, trade addition, Chris Sale, Lucas Giolito.
The Red Sox need to make sure they acquire enough starting depth so they don’t have to rely on Chris Sale to start 20 or more games in 2024, the final year of his contract. Crawford showed he can stick in the rotation long-term but he needs to go deeper into games.
3. The most significant trade Craig Breslow makes in his first winter with the Red Sox will be:
COTILLO: Acquiring George Kirby (or Logan Gilbert) in a blockbuster trade with the Mariners.
The Mariners flirted with trading away a young starter at the deadline and would be wise to at least explore the market again this winter. In Kirby, Gilbert, Bryce Miller and Bryan Woo, the Mariners have plenty of super intriguing young arms. Jerry Dipoto loves to deal. Could a package of Marcelo Mayer, Kutter Crawford and a year of Alex Verdugo get a trade done?
MCADAM: Trading Alex Verdugo.
There’s some debate about how much Verdugo will bring in return with only one year of control remaining, but the guess is that Alex Cora has had it with him. And given that there’s no evidence that the Sox are interesting in extending him, why not get something for him now?
SMITH: Alex Verdugo and a top prospect for a controllable starting pitcher.
Verdugo, who was benched twice in 2023, could use a change of scenery. He’s entering his walk year and so the Red Sox would need to package him with a top prospect such as Roman Anthony or Marcelo Mayer to acquire a young, controllable starter.
4. On Opening Day, Alex Verdugo will be:
COTILLO: Traded away… as part of a bigger deal.
The Red Sox aren’t going to get a ton back for Verdugo, who did not have a good second half, has only a year left under control and comes with his warts. But they still want to see if they can unload him and might have to do it in a larger deal (see above) to do so. If the Yankees want to re-visit a Verdugo-for-Clarke Schmidt trade that was discussed at the deadline, the Red Sox should try to do that.
MCADAM: Elsewhere. Guessing San Diego.
The Padres could end up cutting payroll and dealing off either Juan Soto or Fernando Tatis Jr., so they could use outfield reinforcements. Verdugo is relatively affordable and available.
SMITH: A Miami Marlin.
How about dealing Alex Verdugo to the Marlins with a top prospect for 25-year-old fireballer Edward Cabrera who is under team control through 2028? White Sox righty Dylan Cease is another potential starting pitching target. He’s under control through 2025.
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5. An-outside-the box move Breslow will make is:
COTILLO: Trading Chris Martin to a team looking for a closer in a sell-high move.
Martin was arguably Boston’s best player in 2023, absolutely dominating in a setup role ahead of Kenley Jansen. The Sox are excited they’ll get to run back that duo in 2024. But why not look to deal the 37-year-old Martin to a team looking for a proven bullpen arm? His value will be super high. Whitlock, Houck, John Schreiber and Josh Winckowski are options to slide into the eighth inning.
MCADAM: Engage in trade discussions on Marcelo Mayer.
I don’t think the Red Sox are intent on dealing their top prospect, but I would imagine Breslow would at least be willing to listen. Remember, he has no attachment to Mayer, and with Trevor Story under control for four more years, might see Mayer as a valuable trade chip.
SMITH: Trading Kenley Jansen and make Chris Martin, Garrett Whitlock or Tanner Houck the closer.
Whitlock and Houck have had success in late-inning bullpen roles and closed out games part-time. The Red Sox should view them going forward as relievers, not starters.
6. Justin Turner will:
COTILLO: Leave the Red Sox and sign a two-year deal with a contender:
The Red Sox are sure to try to Turner back after a great season but might be outbid by a team looking to give him two guaranteed years. Arizona looms as a clear threat. The market for Turner, a great clubhouse leader, will be strong.
MCADAM: Sign elsewhere.
Turner was a great fit here for 2023 and loved playing in Boston; presumably, he’d like to stay. But he’ll undoubtedly be looking for a two-year commitment at a time when the Red Sox are looking to find ways to get some suspect defenders (like Rafael Devers and Masataka Yoshida) some DH time.
SMITH: Re-sign with the Red Sox for one year, $14 million with a mutual option for 2025.
Turner does a tremendous job both grinding out at-bats and serving as a leader. He’s critical to both the lineup and clubhouse.
7. Of their own free agents, including James Paxton and Adam Duvall, the Red Sox will re-sign:
COTILLO: Duvall and Adalberto Mondesí.
On paper, Duvall isn’t a clean fit because the Red Sox have too many outfielders already. But his swing is made for Fenway, the organization really likes him and he could fit well if Verdugo is traded. Boston needs some right-handed pop in its outfield mix. Mondesí might re-up on a minor league deal because of his comfort with Boston’s training staff, which worked with him throughout 2023.
MCADAM: Duvall.
I expect there will be a lot of moving parts to the outfield picture, with Breslow willing to deal almost anyone. The Red Sox could use a right-handed power bat, and retaining Duvall at a reasonable number makes sense — especially if he signals a willingness to play some first base.
SMITH: Turner.
The Red Sox need his right-handed bat back in their lineup.
8. The young Red Sox player most likely to sign a long-term extension this winter is:
COTILLO: Jarren Duran.
Triston Casas and Brayan Bello are the clear top priorities on the roster in terms of long-term extensions but the Red Sox would be smart to talk to Duran about a deal, too. Don’t count out the idea of him trying to cash in on a breakout season and giving the Sox a long-term, high-upside option in their outfield.
MCADAM: Triston Casas.
Casas has repeatedly said he’d be open to an extension, and as a young slugger, he provides far less risk than extending Bello.
SMITH: Triston Casas.
He’s going to be special. The rookie finished in the 93rd percentile in walk percentage (13.9%), 86th percentile in chase percentage (22.1%) and 89th percentile in expected slugging percentage (.500).
9. A trade that will send shockwaves through the league will be:
COTILLO: Tyler Glasnow to the Cardinals.
St. Louis might be even more aggressive in its pursuit of pitching than the Red Sox this winter. Glasnow is a prime trade candidate and would be a good fit there.
MCADAM: One involving Fernando Tatis Jr.
While everyone expects that the Padres will move Juan Soto, I wouldn’t be surprised if it’s Tatis Jr. who gets moved. He’s been something of a headache there, and they’d love to get out from underneath his deal.
SMITH: Juan Soto to the Yankees.
New York needs to add an outfielder. It also needs to make a big splash after not making the postseason.
10. Shohei Ohtani will sign with:
COTILLO: Dodgers.
The Red Sox will be in the mix but ultimately will be outbid. The marriage with the Dodgers ultimately just makes too much sense.
MCADAM: Dodgers.
Sometimes, the most obvious answer is the right answer. The Dodgers spent last year clearing payroll for Ohtani and won’t be outbid.
SMITH: Dodgers.
The Dodgers have won 100 or more games the past three seasons but have failed to do anything in the postseason. LA has won just one playoff game in the past two years. The Dodgers can afford the two-way star and he would be able to remain in Southern California.
