5 storylines for Cubs ahead of Winter Meetings

November 27th, 2023

This story was excerpted from Jordan Bastian's Cubs Beat newsletter. To read the full newsletter, click hereAnd subscribe to get it regularly in your inbox.

CHICAGO -- At some point soon, baseball’s big offseason dominoes will begin to topple and trades and free-agent signings will follow in waves. The Cubs should be plenty active on both fronts as they work to build an October-ready roster for next season.

In one week, agents and front-office members from around the league will convene in Nashville, Tenn., for the annual Winter Meetings. The event can often wind up being a tipping point for blockbuster transactions.

With that in mind, here are five storylines to monitor for the Cubs as the Winter Meetings loom:

1. Can the Cubs really be a player in the Shohei Ohtani sweepstakes?
The Cubs were among the finalists to land Ohtani when he came to the Major Leagues six years ago and have the ability to make a run at him again this winter. This is not a case of how Ohtani fits a roster. He fits any roster. This pursuit will come down to where Ohtani sees himself fitting.

The Cubs have a big-market team with a small-neighborhood feel around Wrigley Field. They have a vacant DH slot (plus a need for rotation down the road). Ohtani’s Team Japan teammate, Seiya Suzuki, is under contract for three more years. The Cubs have payroll flexibility. They have a team on the cusp of contention, just reeled in one of the game’s top managers and have a deep farm system with more talent coming.

Could that all add up to Ohtani seeing Chicago as the right fit? That’s the many-millions-of-dollars question.

2. Will Chicago reel in another player from Japan?
The Cubs’ recent history of signing Suzuki and helping him navigate through the first two years of acclimating and adjusting to the States and Major Leagues could help on another front. Yoshinobu Yamamoto and Shōta Imanaga are on the open market and Chicago has a need for impact rotation help. If the market for the 25-year-old Yamamoto climbs too high for the Cubs’ liking, the left-handed Imanaga might be a more realistic target, especially as Chicago tries to balance the cost of impact additions in other areas.

3. How serious will the Cubs be about re-signing Cody Bellinger?
Expect the Cubs to explore adding offense in other ways while waiting out the market for Bellinger, who was an integral piece to Chicago’s lineup and defense in his incredible comeback campaign in 2023. Bellinger remains a great fit for the Cubs, but his asking price will be steep after last winter’s one-year deal. And, hey, if the Cubs want to try their hand at another potentially impactful reclamation project, maybe free-agent first baseman Rhys Hoskins gets a look.

4. How far are the Cubs willing to go to swing a blockbuster trade?
One thing the Cubs liked about the trade for Jeimer Candelario at last summer’s Deadline was that it did not make much of a dent in their farm system. It cost two prospects, but the Cubs still held on to their top farmhands. Chicago will likely aim for a similar approach this winter. The ballclub has the prospect pool to make an impact trade or two, but the Cubs will try to avoid dealing away their top-tier talent. That is where rumors involving short-term adds like Juan Soto, Pete Alonso or Corbin Burnes (free agents next winter) come into play.

5. What impact will Craig Counsell’s arrival have on Chicago’s offseason?
First things first, Counsell has to finish building his coaching staff with the Cubs. There has been no official news on that front, but expect more updates to arrive during the Winter Meetings. It will also be interesting to follow how Counsell’s reputation might impact how a free agent views the Cubs. As an example, Chicago needs relief help and Counsell has a great track record for handling a bullpen.