This has already been an active offseason for the Red Sox, but over the next few days things should really kick into high gear.

The MLB Winter Meetings officially begin today and will run throughout the week in Orlando, Fla. Traditionally the busiest time of baseball’s offseason, the Winter Meetings are typically where many of the biggest free agent signings and trades come together.

So what should fans expect? Here’s everything you need to watch out for in the coming days.

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Will Sox land big bat?

One of the Red Sox’s biggest needs this offseason is finding a power bat to anchor the middle of the lineup, and the club should be among the numerous suitors for the top free agent sluggers.

Kyle Schwarber and Pete Alonso are the top two home run hitters available, ranking second (268) and third (264) in MLB in home runs, respectively, since 2019. Schwarber, who spent half a season with the Red Sox in 2021, is coming off an MVP runner-up season in which he hit 56 homers, and Alonso hit 38, giving him six straight 162-game seasons with at least 34.

Both sluggers could plausibly find their new homes over the coming days.

In addition to Schwarber and Alonso, other sluggers the Red Sox could target include Japanese standouts Munetaka Murakami and Kazuma Okamoto, third baseman Eugenio Suarez and one especially familiar face.

One of the biggest questions looming over the Red Sox this winter is whether or not All-Star third baseman Alex Bregman will return. (AP Photo/Frank Franklin II)

Will Bregman return?

Coming off an All-Star season in his first year in Boston, Alex Bregman opted out of his contract and now ranks among the top all-around players on the free agent market.

Bregman is expected to pursue the lucrative long-term deal he couldn’t land last winter, but whether he’ll get it from the Red Sox remains a mystery.

While Bregman quickly became a popular figure within the Red Sox organization and made a huge impact on the clubhouse, his lone season in Boston did not go off without a hitch. After a red hot start to the season Bregman missed nearly two months with a quad strain and was not as productive in the second half following his return.

Red Sox chief baseball officer Craig Breslow has spoken positively about Bregman since the season ended, but he’s refused to tip his hand about how far he’ll be willing to go to bring Bregman back.

If Bregman does not return the club would have a major void to fill in its infield. Marcelo Mayer could potentially take over as the club’s everyday third baseman, but he has battled frequent injury issues throughout his professional career.

Another big trade?

Last year at the Winter Meetings, Breslow made the biggest move of his tenure so far, swinging a blockbuster trade with the Chicago White Sox to land ace Garrett Crochet.

Could another big trade be imminent?

The Red Sox have already been active on the trade market this winter, acquiring starting pitcher Sonny Gray from the St. Louis Cardinals, infielder Tristan Gray from the Tampa Bay Rays, and most recently starter Johan Oviedo and others from the Pittsburgh Pirates on Thursday.

Those all helped address areas of need, but the Red Sox still have not made a move to clear their outfield logjam. The expectation throughout the industry is that Boston will trade one of Jarren Duran or Wilyer Abreu before next season, and either one could be the centerpiece of a blockbuster deal netting the Red Sox another frontline starter or the big bat they’ve been looking for.

Former Red Sox ace Roger Clemens is among eight candidates on the Baseball Hall of Fame’s Contemporary Era ballot. (AP Photo)

Will Bonds, Clemens make Hall?

As far as officially scheduled events go, the first order of business will be the Baseball Hall of Fame’s Contemporary Era committee vote.

Tonight a 16-person committee of Hall of Famers, MLB executives and media members will consider eight individuals whose primary contributions came after 1980. Any candidate who receives at least 12 votes will earn induction to Cooperstown as part of the Class of 2026.

Two candidates are especially notable.

Barry Bonds and Roger Clemens, who were not elected during their 10 years on the BBWAA ballot due to their association with performance-enhancing drugs, will be up for consideration by the Contemporary Era committee for the second time. The last time the pair were considered in 2022 they did not garner much support, earning fewer than four votes. If they flop again they may not get another shot for a long time.

The other candidates on this year’s ballot are Carlos Delgado, Jeff Kent, Don Mattingly, Dale Murphy, Gary Sheffield and Fernando Valenzuela. The result of the vote will be announced on MLB Network at 7:30 p.m.

Draft Lottery

MLB’s fourth annual Draft Lottery will take place on Tuesday at 5:30 p.m., but unlike each of the previous iterations, the Red Sox will not be involved.

By virtue of reaching the playoffs the Red Sox will not have any shot at landing one of the top six picks in next summer’s MLB Draft. Instead the Red Sox are projected to land the No. 20 pick, though their exact selection will depend on how the lottery shakes out and particularly on whether or not the Mets move up.

The White Sox have the best odds at landing a lottery pick (27.73%), followed by the Twins (22.18%), Pirates (16.81%), Orioles (9.24%) and Athletics (6.55%). The Rockies, despite finishing a league worst 43-119, are not eligible to win a lottery pick after picking in the lottery in back-to-back years. The Nationals and Angels are also ineligible because clubs that pay into MLB’s revenue sharing program, as both teams do, aren’t eligible to land lottery picks in consecutive years.

Red Sox right-hander Garrett Whitlock is one of MLB’s most notable recent Rule 5 Draft success stories. (Nancy Lane/Boston Herald)

Rule 5 Draft

The last major event of the Winter Meetings is the Rule 5 Draft, which is scheduled for Wednesday at 2 p.m.

The Rule 5 Draft serves as a mechanism to give MLB-caliber players a chance to reach the big leagues who might otherwise be blocked within their current organizations. All players who have four or five years of professional experience and who are not on their club’s 40-man roster are eligible, and if selected they are immediately added to their new team’s active roster.

Some recent Rule 5 success stories include Red Sox right-handers Garrett Whitlock and Justin Slaten, along with Danvers’ Shane Smith, who was the No. 1 overall pick in last year’s Rule 5 Draft and went on to earn All-Star honors as a rookie with the White Sox.

The Red Sox do not currently have an open spot on their 40-man roster, which means they would not be eligible to make a selection. If the club opened a spot beforehand, one possible target could be a left-handed reliever. Right now the only lefty relievers on the Red Sox 40-man are closer Aroldis Chapman, and depth arms Jovani Moran and Tyler Samaniego.

Moran only appeared in two MLB games last season, and Samaniego has yet to make his big league debut.

The Red Sox are also likely to lose a handful of prospects to other teams in the draft. Baseball America lists two Red Sox players on its Top 50 Rule 5 player rankings, those being left-hander Hayden Mullins and right-hander Yordanny Monegro, and outfielder Miguel Bleis, who ranks as Boston’s No. 13 prospect according to MLB Pipeline, is also unprotected and eligible.

Chicago White Sox starting pitcher Shane Smith in action during a game against the Washington Nationals on Sunday, Sept. 28, 2025, in Washington. (AP Photo/Nick Wass)