3 mistakes Cubs made while boring their fans to sleep at 2025 Winter Meetings

It was far from an entertaining Winter Meetings for the Chicago Cubs. The only moves made by the North Siders were making a few selections during the minor-league phase of the Rule 5 draft and adding Collin Snider on a minor-league deal.

The main takeaway from the Winter Meetings is that the Cubs are still deciding what direction they want to take this offseason. In part, that could be tied to the fact they have been linked to a highly-coveted starting pitcher on the trade market (and you can't force the other team to make a deal on your schedule), and that they likely are at the forefront of the sweepstakes for Tatsuya Imai--who is meeting with teams next week and has to make a decision by January 2.

3 mistakes Cubs made at 2025 Winter Meetings

By and large, most of the Cubs' offseason targets are still available. On the free-agent market, they can still decide between Imai, Michael King, and Zac Gallen. Searching for offensive upgrades, Alex Bregman, Eugenio Suarez, Kazuma Okamoto, and Munetaka Murakami are all unsigned. Even the trade market has the Cubs' top targets, Edward Cabrera and MacKenzie Gore, untouched.

The Cubs can still have a very successful and impactful offseason, but that doesn't mean they were mistake-free at the Winter Meetings.

Being afraid to set the market

Gone are the days when we can expect the Cubs to set the market for a top free agent. We've had confirmation of that fact multiple times already this offseason. The Cubs weren't willing to match the money involved in Dylan Cease's and Devin Williams' free-agent signings. While they could still spend beyond their comfort zone on a starting pitcher, it won't be because they set the market.

As it pertains to someone like Bregman, it's clear the Cubs like him. Had they just ponied up and sent a Godfather offer to the All-Star third baseman, it feels like a deal could have been made at the Winter Meetings.

Not adding a player during the Major League phase of the Rule 5 draft

The Cubs currently have nine open spots on their 40-man roster, and most of those are tied to the fact that most of the relievers used in their Major League bullpen last season became free agents. There were several intriguing bullpen arms the Cubs could have grabbed in the Rule 5 draft, and it feels like they should have taken that free lottery ticket. At worst, they would have had to send the prospect back if it didn't work out.

Leaking the Pete Alonso meeting

The Cubs' leaked meeting with Pete Alonso at the Winter Meetings doesn't help their cause. For those cynical of the team's offseason motivations, it feels like it was done as a PR ploy by Jed Hoyer and Tom Ricketts.

In actuality, it may have been the Cubs trying to get some insight into the money Alonso was being offered by the Boston Red Sox. Not because they wanted to swoop in and top the offer, but because they wanted to get a sense of what Boston would be willing to spend on Alex Bregman. Regardless of the intent of the meeting, the Cubs likely would have preferred to have it kept under wraps.

These mistakes certainly aren't a reason to put premature grades on the Cubs' offseason, but if we get to spring training with no moves of consequence, we may need to revisit this discussion.