Inside The Cubs

Jed Hoyer Admission Will Change Cubs Fans' Winter Meetings Expectations

The Chicago Cubs offseason continues with nothing major to report on down in Florida.
Jul 3, 2025; Chicago, Illinois, USA; Chicago Cubs president of baseball operations Jed Hoyer speaks before a baseball game between the Chicago Cubs and Cleveland Guardians at Wrigley Field.
Jul 3, 2025; Chicago, Illinois, USA; Chicago Cubs president of baseball operations Jed Hoyer speaks before a baseball game between the Chicago Cubs and Cleveland Guardians at Wrigley Field. | Kamil Krzaczynski-Imagn Images

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Baseball's offseason is where the chess match begins for the upcoming year, as teams compete to patch holes and fill gaps on their rosters.

The Chicago Cubs are one organization that hasn't made much of a splash since free agency started, but that doesn't mean it won't come. Everyone involved with the organization is thrilled to have been a 92-win team last year, but not so thrilled to be sent home in the NLDS.

And while many deals are made during MLB's Winter Meetings, it's important to note that the time is more often used to lay the groundwork for future deals, rather than to negotiate and close them in just a handful of days. And Cubs President of Baseball Operations Jed Hoyer remembers that fact crystal clear.

“I’ve made a lot more deals in the week after or a couple weeks after based on things that happen here, than [I've made] here. If you don’t have close to a deal coming in here, sometimes it’s hard to get there," said Hoyer to MLB insider, Jordan Bastian.

Jed Hoyer
Jed Hoyer | Kamil Krzaczynski-Imagn Images

After the Cubs signed Jon Lester in 2014 during the Winter Meetings, there has always been a bit of an unrealistic expectation from the fanbase to make a significant signing that might lead to a World Series title. And many fans across all of baseball believe this is when the biggest deals of the year happen.

But nine times out of 10, that's not how things play out for any team, not just the Cubs.

Post-Winter Meetings Cubs Acquisitions In Recent Years

Kyle Tucker raising his arms to the sky as he celebrates a home run at Wrigley while running the base
David Banks-Imagn Images

It's hard to forget the blockbuster deal that brought outfielder Kyle Tucker to the Cubs just last season. Tucker was traded by the Astros days after the organizations had met, and even though he was criticized by many for his performance this year, he still performed well enough to take home a Silver Slugger Award.

Tucker slashed .266/.377/.464 with a .841 OPS alongside 73 RBI, 22 home runs and 25 stolen bases.

A year prior, a pair of key players were secured just after the New Year, including starting pitcher Shota Imanaga and outfielder Cody Bellinger (re-signed). Both Imanaga and Bellinger were free agents at the time, and both were excellent additions to the 2024 roster.

Imanaga went 15-3 with a 2.81 batting average to complement 174 strikeouts in 29 starts in his first season with the Cubs. Bellinger made an impact at the plate with a near-identical slash line to Tucker's, with a .266 batting average while slugging .426.

Shota Imanaga
Shota Imanaga | Benny Sieu-Imagn Images

Just because Chicago hasn't been seen in the headlines for signing an elite player yet doesn't mean they won't when all is said and done. The Cubs and Hoyer have said the team will be aggressive this offseason, and considering the players they have been linked to thus far, that appears to be the case.

The current roster is extremely competitive, but needs the final pieces to the puzzle. Fans should trust that both Hoyer and manager Craig Counsell have a plan to get back to the World Series.

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Maddy Dickens
MADDY DICKENS

Maddy Dickens resides in Loveland, Colorado. She grew up with two older brothers, where their lives revolved around sports. She earned a master's degree in business management from Tarleton State University while simultaneously playing basketball and competing in rodeo at the collegiate level. She successfully parlayed a reserve national championship into a professional rodeo career and now stays involved in upper-level athletics by writing for On SI on several different MLB teams' pages, along with some NCAA sites.