3 Things Cubs Fans Should Hope For at the Winter Meetings

The baseball world is flocking to Orlando as the MLB Winter Meetings get underway on Sunday night.

In what has already been an unpredictable offseason — with multiple star players traded and a handful of big free-agent contracts signed — it feels like we’re on the verge of even more action. The Winter Meetings might be the spark that sends everything boiling over.

The Chicago Cubs are positioned to be one of the teams making headlines — for better or worse.

Former Cubs outfielder Kyle Tucker is the biggest free agent on the market and is expected to land the largest contract of the winter. It won’t be with Chicago, but Tucker will dominate the conversation in Orlando. And with every rumor that surfaces about his next home, one unavoidable question follows: What are the Cubs going to do to replace Kyle Tucker?

Meanwhile, the Cubs have already been circling the market for a front-line starting pitcher. They were on the doorstep of major deals earlier this offseason, and the Winter Meetings offer a natural environment for something to finally get done — or for criticism to grow louder if it doesn’t.

So what should Cubs fans be hoping for this week? In my view, there are three realistic checklist items that would noticeably improve the team.

1. Land the Coveted Starting Pitcher

It’s time for the Cubs to get a deal with a top-tier starter across the finish line.

Chicago was deep in the bidding for Dylan Cease before he signed with Toronto for $210 million, eventually getting priced out. Cubs fans then lived through the brief Zac Gallen roller coaster — from Bob Nightengale prematurely reporting a completed deal to quickly walking it back, saying the Cubs were merely “hopeful.”

It’s been quiet ever since.

Whether it’s Gallen, Michael King, or Japanese right-hander Tatsuya Imai, the Cubs need one of the premier arms on the market. And there’s no better window to finalize something than the Winter Meetings.

If the Cubs walk out of Orlando without their guy, it’s going to feel like a disappointment.

2. Sign a Third Baseman

The Cubs have had their eyes on Alex Bregman for over a year now. For the second straight offseason, they’re once again kicking the tires on a deal.

Matt Shaw’s second-half surge was impressive, but if the Cubs truly intend to compete for a World Series — which is now the expectation — adding a proven third baseman is one of the cleanest ways to elevate the lineup.

In the days leading up to Orlando, the Cubs have also been linked to Eugenio Suárez, who hit 49 home runs in 2025 and would bring instant power as a Tucker replacement.

It’s absolutely on the table that Chicago could land one of those two players during the Winter Meetings. Doing so would instantly win back a lot of goodwill from the fan base.

3. Add Another Relief Arm

Phil Maton was a strong first step in rebuilding the bullpen, but the Cubs still need at least one more established reliever.

Outside of Maton, Daniel Palencia, and Colin Rea (assuming he transitions to relief), the bullpen depth is extremely thin. Sure, smaller signings can be made as spring approaches, but adding a reliable late-inning arm now would be a wise investment.

The Cubs, Blue Jays, Tigers, Phillies, and Angels are reportedly all in the mix for a late-inning reliever. It doesn’t need to be a closer, but someone like Luke Weaver or Seranthony Domínguez would fit perfectly.

3 Things Cubs Fans Should Hope For at the Winter Meetings

Tags: