3 Key Items On The Chicago Cubs To-Do List For The 2025 Winter Meetings

Free agency for the majors kicks off as soon as the World Series ends. Even though that was over a month ago, the Chicago Cubs have yet to make any game-changing moves towards improving their 2026 roster.

The Winter Meetings are now rapidly approaching, which will force Chicago's hand. That likely means signing a starting pitcher, which the team has repeatedly confirmed as its biggest priority this offseason.

For those who don't know, the Winter Meetings are one of the biggest events of the offseason, where things like the Rule 5 Draft and Draft Lottery take place, and general managers negotiate face-to-face. This year's will start in two days on December 7th, and run through the 12th.

Winter Meeting to-do list for the Cubs

This time of the year is arguably the most important for the success (or failure) of teams for the next season and beyond. If the Cubs don't want to end their year in the same bitter fashion as 2025, management will need to be proactive. Here are the three main things they need to focus on.

Phillies pitcher Ranger Suarez throwing a ball in a pinstripe unifor — Bill Streicher-Imagn Images

Starting rotation

At first glance, one wouldn't guess that their starting rotation is lacking, as they were tied for fourth with the best ERA in the National League at 3.79. But it was what happened in the second half of the season that is truly concerning.

Shota Imanaga might be back next year, but in his last seven starts, he went 1-3. He let up 38 hits with a 5.40 ERA and 25 earned runs, eight of which came in his last regular-season start alone. Even more concerning was the 13 home runs in those seven starts.

Since Justin Steele won't be available in the beginning months of the season as he will still be rehabbing his Tommy John Surgery, that leaves the rotation to arguably Matthew Boyd, Cade Horton and Colin Rea. It is crucial they sign one more.

The team has already been linked to numerous top free agent pitchers that are available this offseason, including Tatsuya Imao, Michael King, Ranger Suarez, and Zac Gallen.

Relief arm

There isn't a team in baseball that wouldn't value adding depth to their bullpen, but the Cubs could be losing the bulk of their most-used relievers, as Brad Keller, Drew Pomeranz, and Caleb Thielbar are all currently free agents. These three all posted an ERA of 2.64 or lower.

The Cubs did add veteran reliever Phil Maton on a two-year, $14.5 million contract with a team option for 2028. Maton's been a reliable pitcher over the past several years, and last season totaled a 4-5 record and 2.79 ERA with both the St. Louis Cardinals and Texas Rangers

However, if they don't sign back at least one or two others for 2026, they'll find themselves in trouble.

Replacing Kyle Tucker's Production

Kyle Tucker hitting a solo home run in a white pinstripe uniform at Wrigle — Mark Hoffman-USA TODAY Network via Imagn Images

The general consensus across baseball is that the Cubs won't be searching for another left fielder, as their top prospect, Owen Caissie, will be stepping in to fill Tucker's shoes, at least on defense. However, expecting Caissie to replace the 2025 Silver Slugger's production isn't realistic, as even though Tucker slumped last season, his bat was a big part of why they won 92 games.

Tucker at the plate in 2025

.266 Batting Average
.377 On-Base Percentage
.464 Slugging Percentage
.841 OPS

The team will be looking to other players already on the roster, like Michael Busch and Nico Hoerner, to help make up the difference, but they should also consider adding another bat in the coming days. They've been linked to Kyle Schwarber and Alex Bregman, though they might not have the room in the budget.

There will be a lot of moves made in the coming week, and if the Cubs are looking to win the division and be a 90+ win team again, they need to address these areas.

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