Major League Baseball’s annual Winter Meetings begin two weeks from Monday and the Boston Red Sox’s biggest needs remain the same: a top starter to slot in the rotation alongside or right behind Garrett Crochet and a power-hitting bat for the middle of the order. While those boxes have yet to be checked, the Red Sox have already made a series of smaller moves, some of which are likely to impact the team in 2026.

We’ll break down those moves here, in addition to where payroll stands ahead of the Winter Meetings.

The bullpen reshuffling has already begun

In three separate deals last week, the Red Sox signaled that they will be adding to the bullpen at some point this winter to fill out their middle relief depth, particularly left-handed relievers.

In Brennan Bernardino, Chris Murphy and Luis Guerrero, Boston traded away three relievers who had roles in Boston over the last two years. In return, they received Low-A catcher Ronny Hernandez and two utility players in Tristan Gray and Braiden Ward.

The flurry of trades means Aroldis Chapman is the only true lefty reliever currently on the 40-man roster. The team has a few other lefties like Payton Tolle and Kyle Harrison who could see time in the Red Sox bullpen. But as it stands, they are in need of a higher leverage lefty arm, with Bernardino dealt away and lefties Justin Wilson and Steven Matz departing in free agency.

At the GM Meetings, the Red Sox had preliminary talks with different types of relievers. The Red Sox could target lefties with upside similar to Wilson last year like Sean Newcomb, Danny Coulombe or Gregory Soto. However, chief baseball officer Craig Breslow noted that while they’ve checked in on several bullpen options, their main priorities remain adding to the rotation and lineup.

Of the three pitchers traded, Bernardino had the largest impact in Boston, with 55 or more appearances each of the last three years with a 3.65 ERA. Murphy, in his return from Tommy John surgery last season, pitched well in a few critical spots. Guerrero, who debuted at the end of 2024, showed promise with a hard fastball despite sometimes spotty command.

But the Red Sox needed to make room on the 40-man roster for three more pitchers they opted to protect from the Rule 5 draft — lefty Shane Drohan and righties David Sandlin and Tyler Uberstine. Each will compete for a spot in the bullpen come spring, but will otherwise serve as depth in Triple-A Worcester.

A starter for most of his career, Sandlin, who has a 100-mph fastball, transitioned into a relief role last season after a promotion to Worcester. There was hope he could contribute to the Red Sox bullpen at the end of the 2025 season, but he struggled in 14 Triple-A relief appearances with a 9.16 ERA.

Drohan, who was selected by the White Sox in the Rule 5 draft two years ago before he was returned to Boston, will likely pitch in long relief or as a potential spot starter. Last season, he posted a 2.27 ERA in 12 games, 11 starts, for Worcester. Uberstine, in his first season back from Tommy John surgery, posted a 3.58 ERA and 27 percent strikeout rate over 25 games, 21 starts, between Double-A Portland and Worcester.

In a fourth trade last week, the Red Sox sent right-hander Alex Hoppe, a prospect who was Rule 5 draft eligible, to Seattle for minor-league catcher Luke Heyman, a 14th-round pick in July’s MLB draft out of Florida. The additions of Heyman and Hernandez help bolster a thin catching group in the farm system.

Enough money to spend in free agency

On the front-office side, this stage of the offseason is full of meetings with agents and preliminary negotiations ahead of what’s expected to be a busy Winter Meetings. What do the Red Sox actually have to spend on the free-agent market?

FanGraphs has the Red Sox currently on the books for roughly $204 million for the 2026 season, about $40 million below the $244 million luxury tax threshold. Despite trading Rafael Devers and finishing 2025 with a cash payroll below $200 million, the Red Sox went over the luxury tax threshold, which is calculated using player’s average annual salaries, this past season. Breslow has mentioned more than once that the club intends to spend in 2026 to further the goal of playing deeper into the postseason next year.

It remains likely the club will spend beyond the $244 million threshold for 2026. Still, in order to add a frontline starter as well as at least one big bat and a reliever or two, the team will have to be active in both free agency and the trade market.

In free agency, a reunion with Alex Bregman remains on the table while Pete Alonso and Kyle Schwarber continue to be top targets for the lineup. Recently posted Japanese infielder Kazuma Okamoto offers another intriguing fit for the club as a right-handed hitting first baseman.

Among the starting pitchers, Dylan Cease, Framber Valdez and Tatsuya Imai (another recent Japanese star who was recently posted) all figure to be free-agent targets as the Winter Meetings approach.

Last week, the Red Sox designated Nathaniel Lowe and reliever Josh Winckowski for assignment and then non-tendered both of them on Friday. Lowe helped the Red Sox late in the season as a shrewd August signing, but was projected by MLB Trade Rumors to make $13 million in arbitration. That salary can now be used elsewhere. Winckowski, despite playing a key role in 2023, didn’t have as strong a season in 2024 and was injured much of 2025 with right flexor strain. He was also out of minor-league options.

Doubling down on depth and versatility

Though the Red Sox already boasted plenty of utility players on their roster, their recent trades only furthered that depth.

In trading Bernardino and Guerrero, the Red Sox added two utility players in Gray and Ward who will serve as big-league depth for the upcoming season.

The 30-year-old Gray is a left-handed hitter who can play all over the infield with more than 100 games played at first, second, third and short in an eight-year minor-league career. He’s played 47 MLB games over the past three seasons, with a majority of those coming in 2025 for Tampa Bay, when he hit .231 with a .693 OPS in 30 games.

Ward, 26, also bats left-handed. He’s spent the majority of his five-year minor-league career in center field, while also seeing time in left and right as well as second base. Considering he has yet to play in an MLB game, he is likely to add depth to Worcester’s outfield next season.

Ward is not on the 40-man roster, but Gray adds to a growing group of utility players on the 40-man roster that includes David Hamilton, Vaughn Grissom, Nick Sogard, Nate Eaton and Romy Gonzalez. That list omits Kristian Campbell and Marcelo Mayer, who aren’t quite utility players, but they can play multiple positions and their roles aren’t yet defined for the team.

Most of the true utility players mentioned above will shuttle between Boston and Worcester as depth to be called upon at various points throughout the season, but at least one or two of them figure to be designated for assignment as the club makes other moves throughout the offseason.