Red Sox Winter Meetings Round-Up: What We Know Through Two Days

No team has been in the headlines more this Winter Meetings than the Boston Red Sox, who have dominated the news cycle from baseball’s annual offseason meet-up down in Orlando, FL.

From being connected to players in free agency, popping up in trade rumors, World Baseball Classic announcements, injury updates and more, it has felt like the Red Sox have been constantly trending over the last two days.

As we head into the third and final day of the Winter Meetings on Wednesday, here’s everything we know so far:

1. A Kyle Schwarber Red Sox Reunion Isn’t Happening

After constantly being connected to Boston over the past two months, news came down on Tuesday that Kyle Schwarber is ultimately returning to the Philadelphia Phillies, reportedly agreeing to a five-year deal worth $150 million.

Always seen as the team in the poll position, Dave Dombrowski did Dave Dombrowski things and got the deal done for Philly, as the 32-year-old slugger returns to the team he first signed with as a free agent after spending half a season in Boston in 2021.

That’s where the legend of “Kyle from Waltham” was born. And unfortunately for Red Sox fans, that nickname will remain an artifact of the past as he continues on as one of the more beloved athletes in the history of the city of Philadelphia.

But when one door closes, another opens…

2. Pete Alonso Drove To Orlando As Red Sox Rumors Run Wild

On Monday, it was reported that the free agent Mets first baseman was planning on driving to Orlando from his home in Tampa to meet in person with both the Red Sox and Orioles.

On Tuesday, it was reported that Alonso had already met with the Red Sox via Zoom, and that he and the team were in the process of figuring out a time and place to meet-up IRL in Orlando. Disney’s Boardwalk, perhaps?

Later that day, Jon Heyman of The New York Post made it clear on his live stream that things between the Red Sox and Alonso were getting hot and heavy:

“He's coming here, we know that. And the Red Sox are going to meet with him, and the Orioles are going to meet with him. I'm told there are other teams, I don't know who those other teams are. I don't think it's the Mets - the Mets said they feel like they know Alonso, [and] I think Alonso feels the same. I'm not reading anything negative into that, [but the other team] better be the Mets.

“Although, I'm hearing some more buzz that the Red Sox are pretty doggone serious about this. I know the Red Sox liked Schwarber, and obviously didn't get Schwarber. Alonso is a better fit. Right-handed bat, got the Green Monster, their best hitters are left handed. You know, I think they're a real threat."

This, along with Pete Abraham of The Boston Globe’s report from Saturday that said Alonso had the Red Sox “high on his list,” has all the makings of a fait accompli. If a deal gets done sooner rather than later, as super agent Scott Boras suggested it might, it should not come as a surprise to anyone who has been paying attention to this offseason roller coaster.

“Schwarber is obviously one of the best power hitters in the game, and all of these guys that are elite - whether they're 29 or 30 - they see a player who's got five years length at 33, it's obviously a fair quotient for the players that are younger to demand more years,” Boras told the media when asked if Schwarber’s deal would jumpstart the market for Alonso, age 31.

“I think it really shows the demand for power,” he added. “We just don't have a lot of it, and it shows the impact that it has.”

3. Marcelo Mayer Update That Impacts Both Alex Bregman, Ketel Marte

On Monday, Craig Breslow told Gabrielle Starr of The Boston Herald that Marcelo Mayer is recovering well from surgery on his right wrist that ended his rookie season with the ballclub in 2025.

“Everything went really, really well in terms of recovery,” Breslow told Starr. “He’s doing really well, stronger, he’s put on some weight. He looks more physical.”

On Tuesday, podcast host Matthew Crory posted on X that per sources, the Red Sox “would be fine” with 22-year-old infielder as their starting third baseman on Opening Day 2026.

Reading the tea leaves here, the above two nuggets could be signaling two things:

- The Red Sox realize that adding both Alonso and third baseman Alex Bregman this offseason will be too rich for their blood, per their reported self-imposed spending limits, and are planting the seeds of, “We don’t need Bregman, we have Mayer!” It was Bregman’s quad injury in late May that triggered Mayer’s call-up last season, and the 6-foot-3 Califonia-native looked the part with his glove in 44 games for the big league club.

- With the Diamondbacks shopping three-time All-Star infielder Ketel Marte, the Red Sox are sending subtle signals to the 32-year-old that he would have a place to play somewhere in the middle infield at Fenway if they’re able to pull off a deal, as they are - of course - connected to the player, per reports.

Marte, two seasons removed from finishing third in NL MVP voting, can play either second base or shortstop. With Trevor Story opting-in to the final two years of his deal earlier this offseason, the addition of Marte would shore up the double-play exchange for Boston for at least the next two seasons. Regardless of where he’s traded, Marte would be moved with a contract that gives his new team five more years of control, with a player option for a sixth year in 2031. He’s due just $16 million in 2026 and $12 million in 2027 before escalators kick-in in 2028 that bump him over $20 million for the final three years of his deal.

4. Red Sox Fielding Trade Calls On Three Different Starting Pitchers

On Monday, MassLive’s Sean McAdam reported that the Red Sox have fielded trade calls on Kutter Crawford, Hunter Dobbins and Patrick Sandoval.

Crawford sat out the entire 2025 season while recovering from knee and wrist issues, but he’s back to full strength now and will be an important depth piece for Boston if he does stick around.

Sandoval had Tommy John surgery in the middle of 2024, and he’s projected to be ready to go by the time spring training opens. He has yet to play in a game for Boston after being acquired by the team in December of 2024.

Dobbins turned heads in his 13 appearances, 11 as a starter, before a knee procedure ended his 2025 season. Before he tore his ACL in July, Dobbins was 4-1 with a 4.13 ERA across 61.0 innings pitched.

5. More Shortstop Buzz To Sort Through

On Tuesday, Tim Healy of The Boston Globe reported that there’s been discussions between the Red Sox and Rangers on shortstop Corey Seager.

Shortly after this report, my friend and WEEI colleague Rob Bradford said on X that there was “no momentum” when it comes to Boston’s interest in the 31-year-old.

Also on Tuesday, CBS Sports’ Julian McWilliams posted on his X account that he’s hearing the Red Sox are not in on Bo Bichette “unless his market changes.” That runs contrary to a report on Monday night from Ari Alexander of Boston’s 7News that said Bichette and the Red Sox had a “serious” Zoom call that “went well for both sides.”

Until the Red Sox make a move that bolsters their middle infield, we will continue hearing reports like these connecting the team to various shortstops and second basemen.

6. World Baseball Classic Updates

Here’s what we know as of now on who’s in, who’s out for the Red Sox at next year’s World Baseball Classic:

IN:

- Wilyer Abreu (Venezuela)
- Jarren Duran (Mexico)
- Ceddanne Rafaela (Netherlands)
- Garrett Whitlock (United States)

OUT:

- Roman Anthony (Italy/United States)
- Garrett Crochet (United States)

MAYBE:

- Aroldis Chapman (Great Britain)
- Carlos Narvaez (Venezuela)
- Masataka Yoshida (Japan)

Wednesday’s third and final day of the 2025 Winter Meetings in Orlando is already underway.

Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.