The Red Sox took a major step forward in their mission to secure a core for the future earlier this month when they signed starter Brayan Bello to a six-year, $55 million extension that keeps him under control through 2030. Bello’s deal is significant not just because the team locked up its most promising young starter for more than a half-decade, but also because of what it means in the big picture. For years, Boston’s decision-makers have discussed the importance of trying to lock up young players to big deals early in their careers. Bello’s deal marked just the second time since 2011 that the club signed a pre-arbitration player (between 1-3 years of service time) to an extension, with Garrett Whitlock’s 2022 deal serving as the only other.
Fanatics Sportsbook
10X$100 BONUS BET
BET MATCH BONUS
Must be 21+. GAMBLING PROBLEM? Call 1-800-GAMBLER (CO, KY ,MD, OH, PA, TN, VA, VT, WV); (888) 789-7777 or ccpg.org (CT); 1-800-BETS-OFF (IA); (800) 327-5050 or gamblinghelpline.org (MA), mdgamblinghelp.org (MD), 1800gambler.net (WV)
If the Red Sox have their way, Bello’s deal will be the start of a cascade of similar deals. Just a week ago, team president/CEO Sam Kennedy told The Boston Globe’s Alex Speier that the team engaged with other players about extensions, noting that “lots of conversations” were ongoing. It’s unclear if anything else is close. But with just 10 days to go before Opening Day — when contract talks usually get cut off so players can fully focus on the season — it’s not a secret that the Red Sox are trying.
First baseman Triston Casas is an obvious priority, though all indications (based on both what Casas has said in recent weeks and behind-the-scenes chatter) is that nothing is close. Beyond him, a source with knowledge of Boston’s thinking said last week, the team’s young outfielders and promising rotation/swingman candidates, represent “obvious” candidates for deals. Though over the winter, other teams like the Brewers (Jackson Chourio) and Tigers (Colt Keith) extended top prospects who have yet to debut in the majors, the Red Sox aren’t likely to strike a similar deal with one of their top minor leaguers like Marcelo Mayer, Roman Anthony or Kyle Teel in the near future.
Outside of Casas, who had acknowledged preliminary talks this winter, and righty Tanner Houck, who told WEEI’s Rob Bradford that he has had some talks with the team as well, it’s not confirmed that the Red Sox have engaged any other young players. If they have, it’s not public. In late February, MassLive surveyed most of Boston’s top young players regarding talks. At that point, most of them had not heard a word from the team; Bello was the only one to acknowledge momentum.
So who could follow in Bello’s footsteps and sign an early extension? Here’s a look at some other pre-arbitration candidates the Red Sox may have interest in signing (in alphabetical order).
Wilyer Abreu
Abreu doesn’t jump off the page as a prime extension candidate as someone who was never a top-ranked prospect and has just 85 MLB plate appearances under his belt. Internally, though, the Red Sox remain extremely high on the 24-year-old. Alex Verdugo’s antics were the driving force behind the club’s aggressive efforts to trade him over the winter. But they probably wouldn’t have done so if they didn’t trust someone like Abreu to take over in right field on a full-time basis.
Abreu, who got a $300,000 signing bonus from the Astros as an international free agent in July 2017, isn’t a free agent until after 2029. But he could be someone the Red Sox look to lock up very early at a good price. On the team’s end, the deal would have lots of upside. And it’s notable Abreu shares an agency with Bello.
Triston Casas
Casas is clearly the team’s No. 1 priority when it comes to pre-arbitration extensions. The Red Sox think he’s a star and would love to lock him up now in an effort to avoid a situation similar to the ones that played out with Mookie Betts and Xander Bogaerts in recent years. Though Casas has over a year of service time and is under team control through 2028, The Athletic’s Tim Britton recently predicted he could receive a seven-year, $77 million extension if he signed now.
So far, preliminary bids by the Red Sox have fallen short. When Casas arrived at camp last month, he said some discussions had taken place but that the club had offered “nothing enticing.” When pressed on what kind of offer would lead to a deal, Casas offered an interesting response.
“One that sets me and my family up for the rest of my life,” he said. “I don’t know what that looks like. I’m low maintenance. I don’t need a lot. I’ve got a small family. I don’t need much. But something I think would suffice for the work that I’ve put in throughout my whole life.”
While Casas is definitely open to a deal, his personality suggests that he’s not going to settle for anything less than full value. He’s someone who is supremely confident in his abilities — and has only backed up that confidence with his performance to date — so he may very well be willing to bet on himself. Casas has one very good full major league season under his belt. He doesn’t have to rush to sign and a big sophomore campaign could position him for a huge payday.
Kutter Crawford
Crawford’s numbers, both on the surface and under the hood, were much better in 2023 than the eye test would have suggested. The Red Sox view him as a mid-rotation piece for the near future and in today’s game, those guys have value.
Considering how much Boston has struggled to develop homegrown pitching talent for a decade, it’s not out of the question the front office will look to continue the momentum from Bello’s deal by trying to lock up another pitcher. Valuing Crawford, though, is hard because he’s much older (27) than Bello (24) but in the same service time class. He doesn’t have the same upside as Bello and isn’t projected to hit free agency until before his age-33 season.
Jarren Duran
The Red Sox have never had serious talks with Duran about an extension and for much of the winter, seemed more likely to trade him than sign him. But after a really strong 2023 season that included a two-month stretch during which he was one of the hottest hitters in baseball, the 27-year-old seems like someone who could be amenable to a deal. There’s time, as he’s not a free agent until after 2028.
At some point soon, the Red Sox need to decide which young outfielders they view as part of their future and which they don’t. With Abreu, Duran, Ceddanne Rafaela emerging and Anthony due up in a couple years, tough calls will have to be made.
Vaughn Grissom
Grissom is the only player on this list that has not yet appeared in a game for the Red Sox. The 23-year-old was just acquired from an organization (Atlanta) that has had more extensions for young players than any. It would be a bold statement for the Sox to attempt to lock up Grissom before he plays for them but he does have some major league success in his past.
Working against Grissom’s case for an extension is that the Red Sox are hurtling toward a logjam in the middle infield with Marcelo Mayer in the upper levels of the minors, Trevor Story under contract for four more years and other, younger prospects also in the mix. Boston hopes Grissom is the second baseman of the future but there are other options in the organization, too.
Tanner Houck
The Red Sox have talked to Houck about a deal on numerous occasions, including last spring, when he told MassLive that conversations had taken place. He did not do much to raise his value with a poor 2024 and is now a year away from arbitration.
All signs point toward Houck getting another chance to claim a rotation spot this season but he’s hard to value because he turns 28 in June. If the Red Sox wanted to buy out his first two free agent years, that would be for 2028 and 2029. Houck would turn 33 in the second year of that arrangement.
Ceddanne Rafaela
Rafaela only has 89 plate appearances in the majors and there are still questions about his plate discipline, even though he has shown encouraging signs this spring and will likely be the Opening Day center fielder. But the Red Sox, while acknowledging the risk, believe there’s endless upside for the 23-year-old. Teams love pre-arbitration deals because they are centered around securing upside at a potential discount. In that vein, Rafaela would seem to be a strong candidate, with the organization assuming relatively limited risk if he doesn’t pan out.
As of now, Rafaela isn’t set to be free agent until after 2029, when he’s 29. A good season in the big leagues could set him to have a strong case for an extension next winter.
Josh Winckowski
Winckowski’s in a weird spot because he, unlike Bello and Crawford, has yet to establish himself as a major league starter. He won’t get the chance early this season either after being shifted to the bullpen over the weekend. The 25-year-old (26 in June) probably wants to start before cashing in, though that wasn’t a disqualifier for Whitlock two years ago.
Connor Wong
The fact Wong has had some major league success at a difficult position and has just over a year of service time would make him an extension candidate in some organizations. But the Red Sox view top prospect Kyle Teel, who is inching closer to the majors, as their franchise catcher of the future. Don’t be surprised if the club thinks about trading Wong in the next year or two.
