How the Chicago Cubs can win the Winter Meetings?

The Winter Meetings are always an important mile-marker for Major League Baseball's offseason as it often is the catalyst for the major free-agent signings and trade.

On the free agent side of things, all eyes are on Juan Soto. There is a growing expectation that Soto will sign at the Winter Meetings, with the latest reporting being that all offers have exceeded $600MM and Soto has begun to eliminate teams from the process. If you're keeping track of things at home, the Cubs were eliminated when the bidding was at $0.

The trade market could be where the Cubs plant their flag at the Winter Meetings. The latest reporting would suggest the Cubs are in the middle fo the sweepstakes for Chicago White Sox starting pitcher Garrett Crochet. The White Sox are expected to move Crochet before Opening Day with there being a strong chance he is moved by the end of the Winter Meetings.

With the Winter Meetings coming into focus, how can the Cubs come away as winners?

The Cody Bellinger trade

The idea of the Cubs trading Cody Bellinger is no longer a what-if scenario; it has moved to be an expectation once Soto finds his new team. Once the news breaks that Bellinger has been traded, it will be a polarizing day for the Cubs fanbase.

The early messaging surrounding the Bellinger trade reads as if the Cubs are desperate to get out of that contract while giving an extended runway to the team's top prospects. That isn't a reassuring feeling from an organization in a major market that has not reached the the playoffs in a full-season since 2018.

The Bellinger trade can't be a pure salary dump by the Cubs. Whether that means the Cubs take back another inflated contract but a player who can help the Major League team elsewhere, or use the money saved in free agency; the Cubs can't just trade Bellinger for the purpose of getting out of the contract.

Shock the industry

Following the 2023 season, the Chicago Cubs shocked Major League Baseball's landscape at the GM Meetings when they signed Craig Counsell to the largest managerial contract in baseball history. If the Cubs are truly going to win the Winter Meetings this offseason, it will take a move to their Major League roster that rivals their hiring of Counsell last winter.