DALLAS — An empty whiteboard took up a large portion of the Boston Red Sox’s fifth-floor suite at the Hilton Anatole where MLB’s Winter Meetings commenced on Monday.
Less than 24 hours prior, the Red Sox had metaphorically, and perhaps physically, wiped their slate clean after learning free-agent star Juan Soto had chosen the New York Mets.
That whiteboard represented a wide range of possibilities on the table for the Red Sox as baseball’s busiest transaction week began from pursuing free-agent starters to trading for pitchers to adding to the offense to further bolstering the bullpen.
“We have plan A, plan A1, A2, A3, A4, there’s a lot of ways to accomplish what we set out to do,” manager Alex Cora said earlier in the day. “Hopefully we can execute.”
With Soto off the free-agent board, executives across baseball are ramping up for a busy week with movement expected to happen quickly. Even before Soto signed, Red Sox chief baseball officer Craig Breslow thought the market had been more robust than it’d been in years.
“I think it would not be surprising at all for things to be moving pretty quickly,” Breslow said. “Many teams have long considered what the pivot (post-Soto) looks like once we find out where that chip falls. I think it would be unwise going into the offseason thinking this is the single transaction that dictates the offseason. So now we move to all the other pathways we’ve started to design.”
Where the Sox stand in the starting pitching market
With Soto signed, Breslow didn’t mince words about their main focus.
“Starting pitching is our biggest area of need,” he said.
“We’re having a ton of conversations with free agents, with teams, thinking about any number of paths to improving that,” he added. “We have both a need for improving the quality and also the depth. Nobody has yet solved injury prevention and if we find ourselves in a situation where some of our starters start to miss time or start to regress, we want to make sure there isn’t a massive drop off for what we have available. We also want to make sure we are improving the quality and targeting guys who are pitching at the front of the rotation.”
With top free agent starters Corbin Burnes and Max Fried still available as well as other mid-rotation starters in Jack Flaherty, Sean Manaea and Nathan Eovaldi still available, the Red Sox seem likely to be making a decision soon before other teams pounce.
Could a reunion with Nathan Eovaldi be in the cards for the Red Sox? (Kiyoshi Mio / Imagn Images)
“Teams are moving quickly, they’re acting quickly,” he said. “I don’t recall an offseason where this many players have signed at this point. I think that’s indicative of the health of the industry.”
While Burnes and Fried are already 30, and the Red Sox have been hesitant to sign starters over 30 to long-term deals, Breslow said it’s a reality of the market.
“I think you’d be closing off opportunities or pathways if you approach decisions that way,” he said.
Meanwhile, the Red Sox have been tied to Chicago’s Garrett Crochet in trade talks while The Athletic’s Ken Rosenthal has also suggested Seattle starter Bryan Woo might be a fit. Breslow said that while a front-line starter is a priority, he’s willing to trade for a younger, controllable pitcher given the accuracy of protection models in the game.
“If you’re always trading for the bona fide ace, the guy who has established himself, then it’s going to take a pretty significant dent out of your future,” he said. “I think one thing baseball front offices have become pretty good at is recognizing the underlying stats and metrics, especially in pitching, pitch data and performance data and being able to project who is likely to become a top-of-the-rotation pitcher. And our goal is to create this internal development pipeline, that we can complement via free agency or trade, so that we have this constant replenished talent that enables us to not just be successful in ‘25 or ‘26, but for a five to seven year run.”
A focus on the present
The Red Sox have been focused on the future for what seems like years as they waited for their top prospects to mature. Now that their top four prospects, all of whom rank among baseball’s top 25, are knocking on the door, the window for contention has arrived.
Breslow made that clear on Monday.
“As we start to envision the team in 2025 that is capable of competing for the division and a deep postseason run we have to be more willing to address short-term needs,” he said. “Even if to some degree that comes at the expense of the future, knowing there is organizational health given the strength of the farm system.”
While he wouldn’t give a preference as to whether he’d prioritize trading from his young major league pool of Triston Casas, Wilyer Abreu or Jarren Duran or from his top prospect pool of Roman Anthony, Marcelo Mayer, Kyle Teel and Kristian Campbell, it seems increasingly like at least one player from those groups will be traded to bolster the the 2025 club.
KYLE TEEL’S FIRST TRIPLE-A HOME RUN ‼️‼️‼️ pic.twitter.com/bujH8EuriE
— Worcester Red Sox (@WooSox) September 1, 2024
“I think the North Star has to be improving our major league team,” Breslow said. “If there’s the opportunity to do that by trading major league players, we have to be open to it. And if there’s an opportunity to do that by trading prospects, we have to be open to doing that.”
Mayer, who missed the final month of the season with a lumbar strain, is progressing well and has started baseball activities. He’s expected to be a full-go for spring training. The shortstop had once been the top prospect in the system before Anthony’s monster season. Whether that means he’s on the trade market remains to be seen.
The Red Sox agreed to a one-year, $10.75 million deal with Chapman last week, pending a physical. It’s not uncommon for deals to take a while to become finalized, but because it has not officially been announced by MLB, Breslow declined to comment much on Chapman. The reliever was suspended 30 games by MLB in 2016 after being arrested for choking his girlfriend and firing a gun. He was not charged.
Breslow was asked about the process of pursuing Chapman and how deeply his past was investigated.
“I can’t get into specifics until this is finalized, but once that happens, I’m happy to answer all of those questions,” he said.
Breslow did comment from a purely baseball perspective why Chapman intrigued the team.
“I think zooming out a little bit, we all recognize the need for the ability to generate more swing and miss coming out of our pen and we didn’t have premium velocity, premium stuff so we’ve been very open about trying to bring that in,” he said.
When asked once more about the Red Sox perhaps changing their zero-tolerance philosophy on players suspended for violating MLB’s Joint Domestic Violence, Sexual Assault and Child Abuse policy, Breslow said:
“I can only speak from experience, independent of what organizational positions may or may not have been, and again, cannot get into specifics outside of saying, I’m happy to answer this in more detail if and when the time is appropriate. But I would say that it is incredibly important that we do as much work as we possibly can in terms of background and reference. That is true of any decision that we make, and in certain instances, it’s significantly more important. And then ultimately, we need to determine whether or not we’re comfortable with the information that we’re getting.”
Even if/when Chapman becomes official, Breslow said he’s still planning to add to the bullpen.
“That could come in the form of a leverage reliever, it could come as more multi-inning depth,” he said.
Breslow noted Liam Hendriks, who’s recovering from Tommy John surgery, “should be fully healthy and comes with a pretty impressive track record at closing games,” leaving the door open for Hendriks to win the closer’s role.
Breslow also continued to suggest Garrett Whitlock, who’s recovering from an internal bracing procedure, will be in the bullpen mix.
“He was very successful in a multi-inning leverage role, to the point that he was a real weapon that Alex (Cora) could deploy,” Breslow said. “I think for a lot of reasons, beginning with health and managing workload, that could make sense in ’25.”
Missed opportunities in trades and free agency
In one of the more interesting notes from Breslow’s session, he offered some insight into how he’s attempting to evolve as head of baseball operations.
Breslow said he wants to be more decisive this winter and admitted he likely missed out on trades or signings over the past year after seeking returns or dollar figures that may have been too perfect.
He wouldn’t name specific deals, but it was one of the more candid remarks he’s offered.
“I think being more decisive in that often, when wavering on decisions, whether those be pursuits in free agency or trades, you look up and players are off the board, or transactions have taken place,” he said. “You kind of think you otherwise would have done them, and I think that’s the situation that we’re looking to avoid. So when there is an opportunity to go out and sign a free agent or to make a trade, if we wait around for the perfect transaction, we’re likely going to be left with nothing. I think moving with a sense of urgency and conviction is really important as it relates to roster construction.
“I would just say that it’s a feeling that we see a player that’s traded and we would have been involved had we known, or we would have been involved at the value level of the return. It’s ensuring that, No. 1, we are collecting as much information as we possibly can. And then No. 2, when we reach a point that says, ‘Hey, this is a decision that we would make,’ ensuring that we don’t allow perfect to be the enemy of good.”
Soto marks different territory given the enormity of the contract, but the Red Sox have been “in” on numerous free agents over the last two years including pitchers Seth Lugo and Zack Eflin last winter and pitchers Shane Bieber and Blake Snell this offseason. There have been trades, too, that looked like good fits for the Red Sox for relatively little return. If Breslow is seeking to avoid perfection, the Red Sox are likely better off.
(Top photo of Corbin Burnes: Reggie Hildred / Imagn Images)
