The Red Sox arrived in Orlando with momentum, payroll flexibility, and a mandate from Craig Breslow to add impact talent. They left with… well… mostly quotes about “interest,” “options,” and “exploring the market.”
They signed a minor league left-handed pitcher, traded for a Rule 5 pitcher, and jettisoned Vaughn Grissom to Los Angeles.
No breakthroughs. There was a lingering sense that Boston, once again, watched the teams within the American League East pass them by while they held meetings, collected business cards, and enjoyed the hotel coffee.
Everything that you’ll read on social media has the Sox virtually connected to everyone, from every impact free agent to unlikely trade options. The aggregators are bombarding your timeline with hopeful and optimistic messages.
In reality, the Red Sox brass flew to Orlando and failed to execute on their plan. It’s one thing to sit in an interview and lay out your vision for the 2026 Red Sox roster; it’s another not to make an offer to Kyle Schwarber and let a divisional rival swoop in and outbid you for the most logical free agent fit in Pete Alonso.
Plain and simple, Breslow failed to execute.
THE MARTE MIRAGE
Almost every national baseball writer who graced your television screens while on MLB Network said the Red Sox had the pieces to land Ketel Marte. Boston fans know this; it’s been ingrained in the fan base’s DNA for the last six years as the organization focused on drafting and player development.
For the first time in probably 30-plus years, the Red Sox have a surplus of really good pitching. They have depth that stretches from veterans to young hurlers in Payton Tolle and Connelly Early.
Those two pitchers have been coveted by teams around the league, including the Diamondbacks, who are willing to trade their franchise star.
If the Red Sox were to strike a deal with the D-Backs, the cost to land Marte would hurt. An attainable All-Star bat is available, and as of this writing, Breslow has balked.
Meanwhile, three or four other teams stayed involved, and with Alonso and Schwarber off the board, Arizona’s front office leader Mike Hazen can increase his trade demands and force Boston to pay a steeper price.
Marte is owed just $101 million over the next five seasons; it’s considered one of baseball’s most team-friendly contracts for a player of his caliber.
He would immediately address Boston's frequent turnover at second base. He’s coming off a stretch of elite production—36 home runs in 2024, followed by 28 last year—and owns a career .823 OPS with three seasons above .900. A switch-hitter with contact skills, power, and postseason success, he checks every offensive box for a Red Sox lineup desperate for a true middle-order force.
The price tag is either immensely high, or Breslow is using Marte as a smokescreen for another player he truly covets.
THE ALONSO TEASE
The Red Sox did meet with Alonso, which generated all the right headlines—but produced no real momentum.
Alonso reportedly snuck into the hotel like it was a scene from Ocean’s Eleven to avoid being spotted by the media.
All Alonso needed was a few days in Orlando to decide on his playing future. He agreed to a five-year, $155-million contract, earning him the honor of receiving the highest average annual value given to a first baseman. It’ll also be the highest AAV in Orioles history.
Baltimore will hope that Alonso’s contract will age better than Chris Davis’ seven-year, $161-million deal signed in 2016.
The Orioles have a young and dynamic new manager and a youthful core that makes rival executives salivate but still lack the starting pitching depth to withstand the grind of a 162-game schedule.
One thing is clear: the Orioles were bold; they played at the top of the free agent market and landed one of the top power-hitting first basemen in the game.
MUTUAL INTEREST
Boston held a meeting with Bo Bichette—and both sides reportedly left the meeting impressed with one another. Bichette remains an intriguing option, but between the price tag, positional questions, and a dozen other suitors, it doesn’t feel like anything with him is on the horizon.
Bichette, 27, is one of the most sought-after free agents on the market this season, fresh off a 2025 campaign in which he hit .311 with an .840 OPS and 18 homers, 44 doubles, and 94 RBI in 139 games.
If Bichette jumps ship for Boston, the shortstop would likely need to deviate from his natural position, with veteran infielder Trevor Story currently on the roster. Bichette could slide to third base and replace Alex Bregman. He could also shift to second base, which, at this point in his career, might be a natural fit.
QUOTES. SO MANY QUOTES.
Breslow spoke candidly about the need for power, flexibility, and improving the lineup’s identity.
The Sox’ front office leader acknowledged they fell short of landing Alonso. He carefully navigated the media’s questions as if he were walking through a minefield.
“The profile that I’ve talked about wanting to add is certainly one he would fit,” Breslow said. “But these things don’t always line up. We’ve got to make the best decisions we can for the organizations, and players have to make the best decisions for themselves and their families. Now, we’ve got to figure out another way to improve our roster.
“He’s a prolific bat that’s going to be in the middle of the order. He’ll be in our division, so we’ll see plenty of him. Got to figure out how to get him out at this point.”
With the top two premium free agent bats off the board. The Red Sox are left with nothing to show for after three days in Orlando. Breslow is confident that they will be able to enhance their offense in some capacity.
“I still feel like adding some slug into the lineup is a really good place to start,” Breslow said. “That said, if we set our sights on only one or two options and those fall through, we can’t have no alternatives. We’ve got to figure out a way to round out the roster and improve the offense.”
But at the winter meetings, reassurance without action lands flat.
The bottom line: Boston entered the Winter Meetings with clear needs and the resources to address them over the course of three days. They left with no impact bat and many quotes to create another Breslow word salad.
There’s still plenty of time this offseason to make the necessary additions to the 26-man roster. Until the Red Sox actually do that, it feels like they are content with building a good team instead of a great team. There was no sense of urgency, where other teams, particularly in their division, had.
Red Sox fans got a whole lot of stink, stank, and stunk instead.