On Monday, the calendar flips to December, when Major League Baseball’s hot stove often goes from simmering to boiling over.
The Red Sox wrapped up November with a trade for right-hander Sonny Gray, but will they make a big splash at next month’s Winter Meetings, like they did last year?
The Herald’s Red Sox reporters, Gabrielle Starr and Mac Cerullo, discuss.
Sonny Gray, yay or nay?
Gabrielle Starr: The Red Sox made what will hopefully be a rotation upgrade with this week’s trade for Sonny Gray. There’s a lot to like, such as the promising innings-pitched and strikeouts track record, but he didn’t come cheap and a considerable portion of the fan base appears underwhelmed. What do you think of the move?
Mac Cerullo: I like it, more than a lot of Red Sox fans apparently. Gray has been one of the most consistent and reliable starting pitchers in baseball for most of the past decade and his under the hood metrics were much better last year than his 4.28 ERA would suggest. He might not be as flashy a name as, say, Minnesota’s Joe Ryan, but he’ll give the Red Sox rotation a boost.
I’m also not sure I agree with your assessment that he didn’t come cheap. Sure, $21 million is a solid chunk of change, but that’s basically what the Red Sox paid Walker Buehler last year and only a bit more than what Lucas Giolito earned. In terms of asset allocation, taking that money from either one of them and putting it towards someone who should be better strikes me as a great piece of business, especially when they only other thing Gray cost was two promising arms who weren’t top-10 talents and likely wouldn’t have made a huge impact on the 2026 club.
Minnesota Twins starting pitcher Joe Ryan delivers against the Cleveland Guardians during the first inning of a game, Friday, Aug. 1 in Cleveland. (AP Photo/Phil Long)
GS: I like this trade, too. I think Gray’s rough tenure with the 2017-18 Yankees may be coloring this trade for some Red Sox fans, because that was his closest proximity to Boston. I also would bet there are fans who feel this move is too similar to the short-term moves the front office has made in recent years for similarly-aged pitchers, several of which were busts. Twins righty Joe Ryan was more what I had in mind for a Red Sox rotation upgrade this offseason, but the return package would have been significantly bigger; Gray is more in their starter-acquisition comfort zone.
There’s more nuance and upside to this trade than fans in this mindset think, such as the fact that the Red Sox are now developing legitimate big-league starters rather than rebuilding a farm system that perennially struggled in this area, and therefore no longer feel the need to make long-term additions. That said, with the exception of the Garrett Crochet trade last winter, the recent track record isn’t exactly a thrill ride. (And we probably wrote similarly optimistic takes about the Walker Buehler signing last year, and look how that turned out). I’m sure watching the reigning American League pennant-winning Blue Jays ink free-agent starter Dylan Cease to a big contract the next day didn’t exactly pretty-up the Gray trade for Sox fans, either.
And just looking at their projected luxury tax payroll, it will be interesting to see how far ownership is willing to go with spending. The estimated payroll is $224.99 million, just $19.01 million away from hitting the $244 million competitive balance threshold. Some of that money could come off in trades and arbitration outcomes, but if the Red Sox are truly committed to improving the roster, it’s safe to assume they’ll be going over that line for a second straight season.
MC: Absolutely, but the good news is the penalties for going over the CBT don’t really start getting onerous until you’ve passed the second threshold, which this year is at $284 million. If the Red Sox exceeded that they’d have their first draft pick moved back 10 spots, but anything less and all it would cost is money, likely no more than $15 million in taxes. So if that’s a reasonable ceiling, that still leaves the Red Sox nearly $60 million to work with.
GS: Personally, I’d love to see them veer into onerous territory. It’s been a while.
Red Sox right-hander Brayan Bello should be a fixture of the club’s starting rotation going forward. (AP Photo/Pamela Smith)
Who’s staying, who could go?
GS: Aside from Roman Anthony, who is about as untradeable as a player without a no-trade clause can be, who do you think the Red Sox view as keepers?
MC: Well, besides the obvious like Crochet and Gray, I think the least likely trade candidate is Brayan Bello. The Red Sox are making a real effort to build a true championship-caliber rotation, and moving an up-and-comer on a great contract like Bello just before he reaches his prime seems counterproductive. Carlos Narváez is probably untradable too given his fantastic rookie year and the club’s nonexistent depth at catcher, but after that you could imagine a case for trading just about everyone else on the 40-man under the right circumstances.
GS: Agree on all counts, and I would add Ceddanne Rafaela to the list. The Red Sox love his defense, and manager Alex Cora definitely values him highly. Beyond them, I feel like almost everyone is on the table. Who do you think is most likely to be traded, and who do you think the Red Sox would most like to trade?
MC: I think one of Jarren Duran or Wilyer Abreu are as good as gone. They’re valuable pieces who could command a solid return or headline a bigger blockbuster, and while having a lot of outfield depth isn’t a bad thing, having that kind of logjam isn’t sustainable. As far as who the club would most like to trade, it has to be Masataka Yoshida. He’s shown he can be a productive big leaguer, but even when healthy he still has a limited skillset and virtually no versatility. Unloading Yoshida and freeing up the DH spot might also make it practical to keep both Duran and Abreu, and it would certainly make signing Pete Alonso or Kyle Schwarber an easier proposition from a roster perspective.
GS: Agreed on all counts. If we’ve learned anything from the Mookie Betts trade, the fact that the Red Sox reworked Duran’s club option and agreed to a contract for next season does not mean he’s safe. I would also venture that the Red Sox would like to have a more concrete plan for first base, and Triston Casas’ injuries and struggles the last two seasons have made that difficult. They tried to trade him last offseason.
MC: I have no doubt the Red Sox will have some kind of contingency plan for first base, but my guess is they’ll take their shot at the big free agents before getting more creative. I also have a hard time seeing the club trade Casas now, not when his value is at its lowest and there’s still a chance he could bounce back in a big way.
Boston Red Sox outfielder Ceddanne Rafaela celebrates after defeating the Detroit Tigers in a game to advance to the postseason, Friday, Sept. 26 in Boston. (AP Photo/Greg M. Cooper)
Winter Meetings predictions
GS: Last year, the Red Sox made a tremendous splash on the final day of Winter Meetings when they traded for Crochet. (They also made a smaller splash with a significant ripple effect later the same day when they acquired Narváez from the Yankees.) And if you go back to Breslow’s first Winter Meetings at the helm the year before, he also shipped Alex Verdugo for Fitts, Greg Weissert, who was a huge bullpen asset for Boston this year, and Nicholas Judice. I have a feeling Breslow is about to go for a three-peat. Perhaps for the big bat this lineup so badly needs?
MC: The Red Sox need position players and it already feels like the free agent market is moving more quickly this winter than it has in the past. There isn’t a generational figure like Shohei Ohtani or Juan Soto holding things up, so I feel like this winter will be more like the 2022 Winter Meetings, when it was just one big signing after another. I imagine Alex Bregman won’t play things out until February like last year, and I wouldn’t be shocked if Alonso, Schwarber and several of the big Japanese free agents all have homes by the time things wrap up in Orlando. I’d bet at least one of them will be Boston-bound as well.
GS: Teams and players definitely seem motivated to shore up their futures before the Collective Bargaining Agreement expires next fall and all heck breaks loose again. If the Red Sox can’t manage at least one major signing, it’s safe to say something has gone terribly wrong.