Five Questions Facing Red Sox At Very Important MLB Winter Meetings

The Boston Red Sox began their offseason with a crucial decision, hiring Craig Breslow to become chief baseball officer a little over a month after parting ways with Chaim Bloom.

Since then, there hasn’t been a ton of transactions, but that could change over the next week.

The Major League Baseball winter meetings kicked off Monday in Nashville, and a flurry of moves — both in free agency and on the trade market — tends to accompany the annual event. There’s a lot to sink your teeth into this year, too, with Shohei Ohtani available to sign with any team and Juan Soto reportedly being shopped around by the San Diego Padres.

Where do the Red Sox stand as MLB executives get together to wheel and deal? Let’s examine five questions facing Boston.

1. How aggressive will Craig Breslow be in Nashville?
This obviously is an all-encompassing inquiry. Nevertheless, it represents the backdrop for everything that unfolds (or doesn’t unfold). Breslow worked his way up with the Chicago Cubs, but this is the former pitcher’s first time leading a baseball operations department. It’ll be fascinating to see how he tackles the winter meetings, which, often open the floodgates for free agent signings and trades. After all, the Red Sox have work to do, from a roster standpoint, after back-to-back last-place finishes.

2. Is Boston in on Shohei Ohtani?
If Breslow is aggressive, nothing would move the needle like signing Ohtani, the best player on the planet and the most captivating MLB free agent of all time. Even though Ohtani likely won’t pitch in 2024 after undergoing his second Tommy John surgery, there’s no denying his ace potential when healthy. And he’s such an offensive force — not to mention a marketer’s dream — that it’s likely he’ll land a record-setting contract, which could exceed a whopping $500 million. The Red Sox might not have the stomach for such a hefty investment, explaining their low odds to nab Ohtani, but he’ll remain a hot-button topic for as long as he goes unsigned.

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3. How will the Red Sox improve their starting rotation?
Boston’s rotation is littered with question marks. Brayan Bello is a promising younger hurler, Chris Sale showed signs of his former self when healthy in 2023, Kutter Crawford provided stability and either Tanner Houck or Garrett Whitlock could step up as a starter in 2024. But there’s an unsettling amount of uncertainty, especially for a ballclub navigating the American League East, and Breslow has been candid about wanting to bolster the pitching staff. It’s just a matter of how the Red Sox accomplish that goal, as there are plenty of solid options available in free agency and via trade.

Yoshinobu Yamamoto is an eye-opening free agent thanks to his combination of youth (he’s just 25) and upside (a possible No. 1 starter). He’ll also cost a pretty penny on the open market and comes with some inherent risk as a pitcher who has spent his entire professional career in Japan to this point. If he proves too expensive for Boston’s appetite, the franchise may turn its attention to someone like Jordan Montgomery. Blake Snell, the reigning National League Cy Young Award winner, is a free agent, as well. And Corbin Burnes, Shane Bieber, Dylan Cease and Tyler Glasnow are among the starters who were mentioned in trade rumors before the winter meetings.

4. Who’s on second (base)?
The middle infield was a revolving door for the Red Sox in 2023, with Xander Bogaerts’ departure and Trevor Story’s elbow injury throwing a wrench into Boston’s plans. The defense suffered — an all-too-common theme around much of the diamond — as manager Alex Cora was forced to mix and match for basically the entire season. The whole situation wasn’t ideal.

A recent report indicated second base is “a priority” for the Red Sox this offseason — their current internal options include Enmanuel Valdez, Pablo Reyes and Ceddanna Rafaela — and there are several decent options Boston could target. The free agency class is a little light, with Whit Merrifield and Amed Rosario leading the group, but the trade market features a few notable names, including Gleyber Torres, Jonathan India and Jorge Polanco.

5. Will the Red Sox add some right-handed thump?
Consider some of the names penciled into Boston’s projected lineup for 2024: Rafael Devers, Triston Casas, Masataka Yoshida, Alex Verdugo, Jarren Duran. They’re all left-handed hitters. Ideally, Boston will add some balance before Opening Day. Maybe that involves re-signing Justin Turner and/or Adam Duvall. Or maybe that means tapping into free agency for a fresh face, like Teoscar Hernández, Lourdes Gurriel Jr., Jorge Soler or even old friend J.D. Martinez. Whatever the case, the Red Sox need a right-handed bat.