Chicago Cubs winter to-do list: All the tough decisions Jed Hoyer faces and more

When the Chicago Cubs hired Craig Counsell as manager, and re-signed star outfielder Cody Bellinger to a short-term contract, the message was to win championships. Plural.

But it has been anything but that for Counsell in his first year in Chicago, with the Cubs at 77-74 and in second place in the National League Central. For much of the season, the Cubs were a resounding disappointment. Their roster was largely the same as it was in 2023 when they went 83-79, which sounded good in theory, but the lack of bullpen depth and high-end talent and depth ultimately cost the Cubs.

Which makes this offseason pivotal for the Cubs. The good news is that president of baseball operations Jed Hoyer should have financial flexibility to improve the roster this winter. But in handing Counsell the richest contract for a manager in baseball history, Hoyer put the pressure squarely on himself. And if the Cubs don’t make the postseason in 2025, then it’s entirely possible that the Cubs will look for someone new to run their front office.

Here’s three things that the Cubs need to do this winter.

Chicago Cubs free-agent targets

One thing that has stood out this season is the lack of star power on the Cubs’ roster. And if they want to get back to the World Series, or even the postseason, that has to change.

The two most prominent free agents this winter are Juan Soto and Corbin Burnes. There will be plenty of competition for both – Soto’s free agency is expected to exceed $500 million, with the Mets and Yankees in the bidding – so signing either player will not be easy.

Burnes, however, should be the Cubs’ top target this offseason. The right-hander has emerged as one of the best pitchers in baseball and would give Chicago a dominant ace atop the rotation alongside Shota Imanaga, among others. Burnes also has an extensive history with Counsell from their time in Milwaukee and signaled to FanSided at the All-Star Game that he holds Counsell in high regard, saying: 

“I didn’t get a chance to talk to him because I threw the middle game and both teams had show-and-goes on the last day. … I shot him a text afterwards to let him know that I missed him and to keep doing well.

“Couns is obviously a guy I was pretty close with. I talked to him a lot throughout this offseason. He’s someone I’ll always be in contact with because he’s someone who gave me a chance. I became pretty close with him over the years.”

Like Soto, Burnes will be expensive in free agency and it’s entirely possible the bidding exceeds $200 million. After all, it isn’t often that a pitcher as dominant as Burnes – 3.22 ERA in seven seasons, including a 3.06 ERA in 30 starts this season – becomes a free agent. But one thing to keep in mind: Burnes turns 30 years old on October 22.

Will the Cubs be active in the trade market?

The answer is yes. The Cubs are usually active in the trade market and one thing that Hoyer should be applauded for is being creative.

After all, no one expected Hoyer to trade Christopher Morel to the Tampa Bay Rays for Isaac Paredes. No one expected Hoyer to acquire Nate Pearson, a former top prospect with the Toronto Blue Jays, who has posted a 2.57 ERA in 14 appearances since the trade. And no one expected Hoyer to make a push for Logan O’Hoppe at the trade deadline. The Angels rebuffed the Cubs’ inquiries at the deadline, with one source telling FanSided that the Angels have “no interest in trading O’Hoppe.”

Can’t fault Hoyer for trying. But it would come as no surprise to see Hoyer and the Cubs attempt to upgrade the bullpen through the trade and free-agent markets this winter. Upgrading the catcher position, and finding a long-term solution, is expected to be a high priority for the Cubs as well.

What free agents should the Cubs keep?

Here’s the list of the Chicago Cubs’ free agents: Kyle Hendricks and Shawn Armstrong. David Bote has a $7 million club option for the 2025 season and it’s likely the Cubs decline it. Drew Smyly has a $10 million mutual option for 2025 and considering that the Cubs placed him on outright waivers in August, it would appear likely they plan to decline their end of the option.

The most difficult one to forecast is Cody Bellinger, who holds a $27.5 million club option for the 2025 season.

If Bellinger picks up the player option, that would be a massive development for the Cubs. And it’s a realistic scenario. After all, when Bellinger became a free agent following the 2023 season in which he hit .307/.356/.525 with 26 home runs and 97 RBI, he received little long-term interest in free agency. This season, he’s hitting a lesser .270/.332/.438 with 18 home runs and 69 RBI.

Still a strong season, of course, and being another year removed from the devastating shoulder injury he suffered in Los Angeles could give him confidence that this free agency will be different. If he does opt out, re-signing Bellinger needs to be a high priority for Hoyer and the Cubs. But it’s not that simple, and makes Bellinger’s opt out decision one of the most intriguing decisions looming at the beginning of the regular season.