The Red Sox have long stated their desire to hand out contract extensions to young players in an effort to lock them up early in their careers. After years of talk, they crossed the finish line on two such deals earlier this year, extending Brayan Bello and Ceddanne Rafaela for a combined $105 million in guaranteed money.
This winter, the efforts to continue locking up the young core will continue, and there are plenty of targets to consider after a number of young players took step forwards in 2024. Of course, with big trades expected, it’ll be up to chief baseball officer Craig Breslow and his staff to determine who to move and who to sign. Making the right calls there might just define Breslow’s legacy.
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So who might join Bello (6 years, $55M with club option for 2028) and Rafaela (8 years, $50 million with club option for 2032) and sign this winter? Here’s a look at some possibilities:
FOUR OBVIOUS CANDIDATES: Wilyer Abreu, Kutter Crawford, Jarren Duran, Tanner Houck
The four most obvious extension candidates on the roster are the trio of first-time arbitration-eligible players (Crawford, Duran and Houck) and Abreu, who is still a ways away from real earnings after his first full year in the big leagues. All four players are the type the Red Sox want to build around but are also, at least to some extent, each trade candidates after putting together good years. The clock is starting to tick on Houck (three years left under control) while Duran and Crawford are both under control for four more seasons (through 2028). Abreu is not slated for free agency until after 2029.
Houck and Crawford each made at least 30 starts last season and seem like they’ll be anchors of the rotation for years to come, though the decision to give Nick Pivetta the qualifying offer certainly opens the door for a starter to be included in a trade this winter. If not, it’s likely Boston will float extensions to both and the interest will likely be reciprocated due to age. Houck will turn 32 in his first free agent season and Crawford, who is about three months older, won’t hit the open market before his age-33 season. After debuting in their mid-twenties, both pitchers will likely want to cash in soon, even if it limits future earning upside. The Sox have repeatedly approached Houck about a deal in the past; it’s unclear if they’ve done the same with Crawford. Both are now in position to make some real money after proving themselves as starters over a full year.
The Red Sox have never even broached the topic of a deal with Duran, according to a league source, but that could change after a breakout year that saw him become an 8.7-WAR player overnight. The Sox do have a glut of outfielders on the big league roster and at the upper levels of the minors, making Duran a trade candidate if they want to sell high. But as one of the organization’s great recent developmental success stories, they could look to lock him up as well. Duran, like the pitchers, won’t hit free agency early; he’ll be 32 when he hits the open market. Considering speed is a skill that slows with age, he’d likely want to consider cashing in early, too.
Abreu earned $750,000 last year and won’t earn much more in 2025. But he has emerged as a solid lineup presence who won a Gold Glove as a rookie. Buying out a free agent year or two makes sense if the Sox don’t trade him (a real possibility with the White Sox known to be interested as part of a potential package for Garrett Crochet).
THE WILD CARD:
Triston Casas
A year ago, Casas was the top priority for the Red Sox in terms of early extensions. The sides talked, but never came close. Now, after a season that saw Casas play just 63 games due to a rare rib injury, the chances are not high that the sides will come to terms this winter.
The ever-effusive Casas has been clear that he values himself highly and isn’t someone who’s going to sign a team-friendly deal. The Red Sox, after a disappointing season from their first baseman, aren’t likely to offer a premium contract this winter. A source with knowledge of Casas’ thinking said during the late part of the season that he envisions no world in which the sides are able to match up on value at this point. A strong 2025 could change that quickly.
Casas, of course, has been mentioned as a trade candidate, too, but Breslow threw cold water on the idea at last week’s GM Meetings.
AN OUTSIDE-THE-BOX PICK:
Justin Slaten
In the spring of 2022, the Red Sox rewarded Garrett Whitlock — a Rule 5 pick who had emerged as a dominant bullpen piece in his rookie season — with an extension after his first year. History could very well repeat itself with Slaten, who checked every box (when healthy) as a late-innings option for Alex Cora last season.
A year ago, Slaten was a Rangers minor leaguer with all of 8⅓ Triple-A innings under his belt. Now, he’s in the mix to be Boston’s closer in 2025. The Red Sox know Slaten would likely listen, if Whitlock did, if they offered a shiny guarantee just a year into his service clock. It’s improbable a deal for Slaten, who profiles as a reliever on a long-term basis, includes as much financial upside as Whitlock’s contract, which guaranteed $18.75M over four years and maxed out at $44M over six seasons. But Slaten would make a lot of sense to lock up.
THE BIG FOUR:
Roman Anthony, Kristian Campbell, Marcelo Mayer, Kyle Teel
According to MLBTradeRumors, only seven players ever — and just three since 2020 — have signed extensions before their major league debut. Both Detroit (Colt Keith) and Milwaukee (Jackson Chourio) handed big guarantees to top prospects before promoting them last winter. It’s something the Red Sox have never done but have to be open to considering.
Chourio’s deal was for eight years and $82 million while including club options for 2032 and 2033. At the time, he was a consensus top-three prospect in the sport. Might the Red Sox offer something similar to Anthony, who doesn’t turn 21 until May? It can’t be ruled out. Campbell has less of a professional track record, Teel (a Scott Boras client) likely won’t sign now and Mayer is tough to value after two injury-plagued seasons. But it won’t hurt for the Red Sox to at least consider floating deals to the “Big Four” before they even debut. They’re all close enough to the majors to try.
