Red Sox Manager Alex Cora, left, Chief Baseball Officer Craig Breslow and President/CEO Sam Kennedy speak to the media in October. Breslow said it is time for the Red Sox to build on the young core of talent currently on the roster. TNS

Starting Monday, Chief Baseball Officer Craig Breslow will oversee the Red Sox’s efforts at the Winter Meetings, his second year in charge.

Last year, newly hired, Breslow was handcuffed by payroll limitations imposed by ownership and directed an offseason that was largely uneventful. Though a few trades were made over the winter, the Red Sox signed just two major league free agents from the end of the previous season until the start of spring training.

This year, things are different. The Red Sox have already added two bullpen arms (Justin Wilson and Aroldis Chapman) and remain very much in the running for free-agent outfielder Juan Soto, while also engaging in talks for some front-line starting pitchers.

Breslow spoke with MassLive.com on the eve of the winter meetings and discussed a number of topics:

• The Red Sox are being perceived differently this winter.

“It’s time to deliver,” said Breslow. “It seems like what (information) has been made available publicly is that people are picking up a more aggressive posture (from us). But then again, it’s hard for me to be the person answering the question about how others are responding to us.”

Breslow said that in discussions to date, the point being made repeatedly is the strength of the team’s player development system, the prospects emerging, and the presence of talented young players already on the major league roster.

“Not just agents, but players that we’re talking to,” said Breslow, “are aware of the strength of the system and the young core of guys like (Wilyer) Abreu winning a Gold Glove, and Jarren (Duran) having an 8.0 win (WAR) season and Ceddanne (Rafaela) playing shortstop and center field. And they also look at four of the top 25 prospects in baseball who finished the season at Triple-A. When you can paint this picture of a young core that’s established itself in the big leagues and a secondary wave that’s not far behind and will be impacting the team as early as 2025, I think people are realizing this is absolutely an organization going in the right direction, one that’s going to compete in the short term, but also, for a number of years.”

The Red Sox are reportedly in the running to sign star outfielder Juan Soto, but Chief Baseball Officer Craig Breslow said Boston has a number of plans this offseason. Julio Cortez/Associated Press

• The Red Sox are navigating several paths to roster-building, with multiple balls in the air at the same time.

Breslow couldn’t speak about the pursuit of any individual free agent or trade target, but he seemed to be making a reference to Juan Soto.

“I think the one thing we want to avoid,” said Breslow, “is putting ourselves in a position where the success of our offseason hinges on a single transaction. Because there’s just too much uncertainty around any of that. We have to constantly think about, ‘OK, this is Plan A, but if that falls through, what does Plan B look like and what does Plan C look like?’ And so on. I don’t think anyone has the tolerance for us to come out in February and say, ‘The success of our offseason hinged on this single transaction and we failed there, so therefore our offseason didn’t work out.’ That’s not good enough.

“That versatility is beneficial for a number of reasons. One, is that it does open up different pathways to improving the roster because we have the flexibility to slide guys in and out and a number of guys who can handle multiple positions. And once the season rolls around, we’ve seen how aggressive Alex (Cora) is in managing the game and trying to create optimal matchups.”

• As they pursue various starting pitching options, the Red Sox are very much aware that the infield defense has to be upgraded.

“We’re very mindful,” he said. “I watched 162 games and recognize that a big part of the equation, especially for a starting rotation that primarily relied on managing hard contact and pitching in the zone, is the ability to convert balls in play into outs and we didn’t do that well enough. That’s a responsibility we all share. We made some changes to the (coaching) staff.

“At the same time, there are opportunities that we can take to improve the structure of the workday and really target defense. Part of the reason that we felt so excited about bringing up (first-base coach Jose Flores) from Worcester to the big leagues is the role he had in coaching the infield defense over the last few years and the improvements that we’ve seen, specifically with a number of people who are going to be in the big leagues.”

Breslow also noted that a return to full health for two players on the left side of the infield – shortstop Trevor Story and third baseman Rafael Devers – will result in improvement. The team led all of MLB in infield errors.

• Breslow seemed to downplay the likelihood of moving Rafael Devers to DH or first base.

“As we think about upgrades on the position player side,” he said, “it takes an incredibly talented position player to represent an improvement upon what we already have. When you compare that to pitching additions, where we have holes in our rotation, we’re going to realize all of the value of guys that we bring in. But the base that we’re starting from on the position player side, fortunately, is pretty good.”

• The Sox are open to uncovering some relievers on the market who might have the ability to start.

Last year, the team had interest in both Jordan Hicks and Seth Lugo, who made the transition. This year, Clay Holmes is one more example of a pitcher being marketed as a candidate to transition from reliever to starter.

“It’s definitely something we think about and bat around,” said Breslow, “as we try to find solutions to problems in a way that might be different than our 29 other competitors because competition is really fierce and we need to figure out how to leverage an advantage. So if there are guys we think can handle an additional workload and have the ability to get both lefties and righties out and throw enough strikes to get through the order twice … that’s one path.

“We’re open-minded about all of these things. In a perfect world, you’ve got five starters who shoulder 200 innings apiece, but that’s just not how things tend to go anymore.”

• The team expects to realize improvement over the next week and beyond.

“One thing I’ve learned in 12 months is not to enter the winter meetings with a shopping list,” said Breslow, “and expect that, in three or four days, you’re going to work through the entirety of it. But I think we have a pretty fair understanding of our needs. It’s just so difficult to predict timing because we alone can’t force a decision – whether in conversation with other teams around trades, or with free agents.

“We’ve done a good job canvassing what the markets look like, but we need to move from this idea of talking about things to actually executing them.”