The Winter Meetings is one of the largest off-season events in Major League Baseball. Key baseball operations executives, players, agents, and media all gather in one location to discuss trades and sign free agents.
While it's not as prestigious an event as it was in the past thanks to how easily teams can communicate nowadays, it can still lay the groundwork for future trades or signings.
The 2024 Winter Meetings will take place December 9-12 in Dallas, TX. Over the next week, there will be pressure on many of the contending clubs to improve their active roster. When looking at which teams face the most pressure to build a roster capable of making the postseason in 2025, these three come to mind.
Chicago Cubs
Since Jed Hoyer supplanted Theo Epstein as the President of Baseball Operations in November 2020, the Cubs have never made the postseason. His tenure is marked with trading key players from the 2016 championship squad and failing to adequately build a team strong enough to get back in the postseason. His contract is set to expire after the 2025 season, essentially making this a "do or die" winter for him.
Looking at the Cubs' current roster, they have a lot of solid complementary players but no stars to anchor their lineup, rotation, or bullpen. According to Baseball Reference, they had five players produce at least 3.0 Wins Above Replacement (four hitters and one pitcher). However, no player exceeded Dansby Swanson's 4.0.
The Cubs need to go make a splash and land star players to put them over the hump. The National League Central couldn't be more winnable despite the Brewers seemingly having a stranglehold on the division in recent years.
The Cardinals are mired in their first rebuild in a long while, the Pirates and Reds are trying to figure out how to compete with minuscule budgets, and the Brewers are set to lose their best position player in free agency. The window to strike for the Cubs is now.
Hoyer will have his work cut out to lure a top free agent to Chicago. Whether it's a top of the rotation starter like Corbin Burnes or Max Fried, an impact bat like Alex Bregman, or a back of the bullpen arm like Carlos Estevez, that's the caliber of players the Cubs should be targeting in free agency.
If they opt to go the trade route instead, they have a solid core of players plus near-major league ready prospects at the top of their system.
To date this offseason, the biggest move they've made is signing left-hander Matthew Boyd to a two-year, $29 million deal. While Boyd is solid back of the rotation depth, he doesn't necessarily move the needle forward for them.
Given his current contract status, Hoyer simply cannot afford to do half-measures when assembling the roster. Looking at the National League playoff picture, the Cubs not only will have to contend from within their division, but they'll also have to compete with the Padres, Diamondbacks, Mets, and Braves in the National League Wild Card race in 2025. Should Chicago fail to make the postseason, they could be moving on from Hoyer.