Chicago Cubs: What could happen at this year’s Winter Meetings

The front office knows the team is full of holes on the current roster. What can we expect during this year’s GM Winter Meetings for the Chicago Cubs?

Theo Epstein and other Chicago Cubs executives are gearing up to head to San Diego for the annual Winter Meetings this weekend. This is typically the time when rumors really start to heat up, bigger moves begin to be made and the direction of a team in the upcoming season becomes more defined. This year’s gathering of baseball executives see the Cubs in an odd spot.

It is incredibly unlikely, next to impossible really, that big free agent moves a-la Gerrit Cole, Anthony Rendon or Stephen Strasburg will be discussed. However that does not mean significant moves cannot be made. There are tons of rumors swirling around already regarding core players on the roster being dealt this winter, and the stove could very well heat up whether moves are made or discussions intensify. This is obviously just one of the many possibilities that can happen.

It is hard to believe that the Cubs will do absolutely nothing in these meetings. They know what position they are in and that they are going to have their work cut out for them to move forward both in 2020 and beyond. What can Cubs fans suspect or have strong feelings about regarding to what will happen during this year’s Winter Meetings? Here are a few strong possibilities.

Chicago Cubs: As some of the free agent dominoes have begun to fall, the value of others still without a team seem a little clearer. Who will the Cubs be able to “afford”?

Here is what we already know, the Cubs will not be opening the wallets to give out huge amounts of cash this winter. As previously mentioned the top-tier free agents are as of right now out of the question of possibility for the Cubs. But what about the next tier? What will the Cubs be willing to actually spend?

More from Cubbies Crib

• Cubs should keep close eye on non-tender candidate Cody Bellinger
• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs are giving pitcher Javier Assad a deserved shot
• Cubs: It’s time to start thinking about potential September call-ups

There are plenty of other free agents out there, including Nicholas Castellanos. The hopes in resigning him seem a bit iffy right now seeing what the likes of Zack Wheeler got and knowing who Castellanos’ agent is. Reports are still saying they are perusing him so the dream of that is not dead, but, still iffy for the time being. Especially with other teams with more open wallets interested in him.

Other names on the board like Yasiel Puig, Dallas Keuchel, Josh Donaldson, Corey Dickerson, Howie Kendrick and Madison Bumgarner, just to name a few, will be valued at different ranges.

Just seeing who the Cubs are “in-on” can say a lot about what kind of budget they are on for 2020 whether or not they actually sign someone during the meetings. Right now most of the “hot stove” rumors surrounding the Cubs are trade proposals but interest in some free agents whether bigger names like listed or much smaller ones will certainly heat up during that time.

Do not be surprised if a few cheaper players i.e. recently non-tendered ones are signed as well.

Chicago Cubs: A hypothetical contract extension could very well happen during the meetings based on reports.

While other core players are being involved in trade rumors, the likes of Javier Baez have not been. It is safe to say he is among that crowd that is practically untouchable. This is based on how much the franchise values him and the discussions regarding a potential contract extension.

Reports from NBC have stated that the two sides (Baez and the Cubs) are working towards that extension goal. These reports have originally come from Sun Times reporter Gordon Wittenmyer. On top of that, reports from Jeff Passan have also suggested they could be working on it during the Winter Meetings. To Passan’s point, it makes a lot of sense to lock up Baez sooner than later.

I myself do not have a bunch of sources or a crystal ball, but I think we will see that Baez extension come during this time. I cannot 100% guarantee it but the gut has spoken. If they have been working at this for some time and do indeed talk during the meetings it would just make a lot of sense to see it happen sooner than later. Do not be surprised if we indeed see that contract extension for El Mago happen around the time of the meetings.

This year’s Winter Meetings can be interesting without being overly exciting at the same time. Do not expect shiny new toys, but maybe an idea of which toys will be kept and which ones will be parted with.