Red Sox 2024 predictions: Contract extensions, Alex Cora’s future and a new second baseman

Sep 6, 2023; St. Petersburg, Florida, USA;  Boston Red Sox first baseman Triston Casas (36) looks on while on deck against the Tampa Bay Rays during the third inning at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-USA TODAY Sports
By Jen McCaffrey
Dec 29, 2023

It’s that time of the year again when we make predictions for the upcoming season.

We’ve done this each of the past four years with some degree of accuracy and some laughably bad outtakes, so take these predictions with a grain of salt over your holiday ham.
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This season will be Craig Breslow’s first as chief baseball officer, and with that there’s a lot of uncertainty but also a lot of opportunity. How will the moves he’s made pan out? Are the Boston Red Sox inching closer to contention?

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Let’s take a crack at some easy and outlandish predictions for the 2024 season.

A contract extension for Triston Casas and/or Brayan Bello

We’ve had this one on the predictions agenda before, but now that each has a full big-league season under his belt, it seems like a perfect time to get this done. Both had rookie struggles at different points throughout the season, but both look like players around which the Red Sox need to build their future rosters. Casas is a slugging and on-base machine who could provide the one-two punch in the lineup alongside Rafael Devers that the Red Sox need. Bello looks like the first homegrown starter to stick in the rotation since Clay Buchholz. Casas turns 24 this season while Bello turns 25, and both are entering the prime of their careers. There are pressing needs the team has to make first, but extensions often get done in spring training. Keep an eye on this one in the coming months.

Marcelo Mayer debuts in September

The Red Sox could have more than one top prospect debuting late in the season depending on what kind of year they have, but we’re going with Mayer here. The highly-touted top prospect in the organization is coming off a year in which a shoulder injury dampened his production. But he’s had a healthy offseason and is one of 11 players heading to Fenway in early January for the Red Sox Rookie Development Program. It’s a five-day program that focuses on prospects’ assimilation into major-league life on and off the field and is geared toward players who are expected to debut within the next year or two. Mayer will be attending along with Roman Anthony, Kyle Teel, Chase Meidroth, Nick Yorke, Nathan Hickey, Isaiah Campbell, Richard Fitts, Wikelman Gonzalez, Luis Perales and Justin Slaten. The Red Sox have a history of promoting top prospects in August or September to prepare them for the following season, so Mayer, Yorke or Teel, perhaps even Anthony, could be in that mix while Gonzalez, Campbell and Slaten are pitchers on the 40-man already who might help at some point this season. Perales might be a bit further out, but he is also on the 40-man. Slaten is a Rule 5 draftee and has to be on the active roster all season or be sent back to the Mets, so he’s among the first in this group you’ll see.

Masataka Yoshida has a more consistent season

Yoshida started strong last year and then hit a wall in the second half. After a full season in the majors adjusting to travel, the pitchers, playing on grass versus turf and all the other cultural challenges this past year brought, I’m predicting a stronger year from Yoshida, and that goes for the defensive side, too. I don’t think he will be a Gold Glove winner by any means, but I don’t think he’s as bad defensively as he was last year, and I think a full spring and work this winter will show that. Offensively, over 140 games, he posted a .783 OPS and 109 OPS+, making him about 10 percent better than a league-average hitter. It’s not outlandish to think he’s capable of getting over .800 and posting a 120 OPS+. For what it’s worth, the Red Sox had three players with an OPS+ of 120 or better last season: Casas (129), Devers (126) and Jarren Duran (121). Adam Duvall posted a 119 OPS+ and Justin Turner a 114 OPS+.

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Chris Sale makes 25 starts

This is a bold one, but hear me out. I think I’ve predicted a health-ier Chris Sale each of the past three seasons, but he’s coming off a 20-start season and this is the final full year of his deal. He doesn’t ever seem to need motivation, but finishing out this disappointing contract on a high note is something Sale surely wants. Speaking of the contract, technically Sale has a vesting option for 2025 if he finishes in the top 10 in American League Cy Young Award voting and is not on the injury list at the end of the season. If those two things happen, the Red Sox will have a better chance at competing this year and he’d be back for another season. Either way, this is a big year for Sale.

Alex Cora signs a contract extension at the end of the season

In keeping with the contract theme, this is the final year of Cora’s contract with the Red Sox. He’s joked he’s grateful to Craig Counsell for his megadeal of $40 million with the Cubs, but it’s clear Cora is hoping to use that deal as leverage for his future. Breslow didn’t get to pick his own manager when he was hired, and this is surely a year in which they’re feeling out their relationship. I think Cora stays here for at least another few years before turning his eyes toward a GM-type role.

Could Brandon Drury be the second baseman of the future for the Red Sox? (Bruce Kluckhohn / USA Today)

The Red Sox trade for Brandon Drury at second base

I’ve written too many times about how much this makes sense this winter, so I’m putting it down as a prediction. Not only was Drury among the best defensive second basemen last season with a plus-5 outs above average, he’s a right-handed bat who posted a 114 OPS+. He’s also in the final year of a deal in which he’ll make $8.5 million, leaving the door open for Mayer or Yorke in the middle infield. If the Red Sox don’t go after Drury, Ha-Seong Kim is another strong trade option. A right-handed bat, Kim posted a 110 OPS+ last season with a plus-7 OAA at second and is also in the final year of his deal, making $8 million. The Athletic’s Dennis Lin reported San Diego is looking to cut payroll, and Kim could be on the market. This prediction is likely to be resolved the quickest of any here, so we’ll see how this plays out soon.

Devers hits 40 homers

The lefty slugger has never hit 40, with 38 in 2021 as his career high. A year removed from the contract stress and drama, here’s predicting Devers, who ended up with a solid 2023, will build on that in 2024 as the threat of Casas behind him in the lineup continues to give him a boost.

Tanner Houck makes more starts than Garrett Whitlock

Is this the year the Red Sox finally decide on more defined roles for Houck and Whitlock? It seems with this new pitching system initiated by Breslow and implemented by director of pitching Justin Willard, the team will want to set each on a more direct path. Both are being stretched out to start as the Red Sox vie to keep their options open this winter with the idea that work can be scaled back easier in spring training. Nevertheless, I’m predicting Houck ends up in the rotation and Whitlock in the bullpen.

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A bullpen mainstay from last season will begin the year in Triple A

So much of the winter has been focused on the rotation, for good reason, but there are several questions about how the bullpen will shake out. Kenley Jansen and Chris Martin appear to be the only locks at this point with Rule 5 draftee Slaten also needing to remain on the roster all season. Bryan Mata and Mauricio Llovera are out of options and can’t be sent to Triple A but might be squeezed out unless they have terrific springs. Of the remaining big-league options for the bullpen, several have minor-league options, meaning things might look different come Opening Day. The familiar names with options include Brennan Bernardino, Josh Winckowski, Kutter Crawford, John Schreiber, Zack Kelly, Brandon Walter, Chris Murphy and Joe Jacques. Newcomers Cooper Criswell, Greg Weissert and Isaiah Campbell all have options, as well. Interestingly, Breslow has mentioned more than once wanting to stretch out Winckowski to start. The right-hander began his big-league career as a starter before finding success in the bullpen last season. But his ability to get lefties and righties out has intrigued Breslow, who thinks there’s an avenue for him to become a successful starter. Does Winckowski begin the year in Triple A stretched out in the rotation? Maybe it’s Schreiber who’s the odd man out. Or perhaps Crawford starts in Triple A until he’s needed in Boston. Either way, there are more options than spots, so here’s predicting the bullpen will have some surprising names come Opening Day.

The Red Sox squeak into the playoffs

You need some holiday hope, so we’ll put a prediction in here to boost your spirits for the new year. It’s going to be a tough AL East no doubt, and the Red Sox haven’t done enough yet to improve the club. It’s obvious they need to add solid pitching to the rotation, and if they don’t, this prediction will be moot. But there’s always a team in the division that underperforms and another team that is always riddled with injuries. Last season, the Red Sox dealt with their fair share of injuries and were still within the third wild-card spot as late as mid-August. The playoffs are a crapshoot — just ask the Diamondbacks — so if the Red Sox add pitching and can survive the season and find a way in, it could be interesting. Of course, there are many ifs and many things that have to go right for the Red Sox to have a better 2024. They’ve gotten in their own way too many times of late. Maybe this will be the year it finally starts to come together.

(Top photo of Triston Casas: Kim Klement Neitzel / USA Today)

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Jen McCaffrey

Jen McCaffrey is a staff writer for The Athletic covering the Boston Red Sox. Prior to joining The Athletic, the Syracuse graduate spent four years as a Red Sox reporter for MassLive.com and three years as a sports reporter for the Cape Cod Times. Follow Jen on Twitter @jcmccaffrey