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Chicago Cubs set for a spending spree to restock depleted roster?

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Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel.

The Chicago Cubs are currently sporting a bare-bones 40-man roster, with a staggering nine open slots currently available.

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That didn’t change after Wednesday’s Rule 5 Draft, when the Cubs had a chance to pick up a MLB-able fringe asset or two to add to the roster (Although they DID pick up three minor league players).

The team’s inactivity in the draft and their relative inactivity so far this offseason is leading to speculation that some big things are about to happen. Realistically, though, big things pretty much HAVE to happen pretty soon as a 40-man roster consisting of 31 players is not exactly a recipe for regular season success (By comparison, the team with the second fewest players on their 40-man roster is the Texas Rangers, with 34).

Filling the Chicago Cubs’ barren 40-man roster

Alex Bregman, Chicago Cubs
Sep 24, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) hits a single against the Toronto Blue Jays in the first inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images

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Matthew Trueblood of Northside Baseball recently wrote that the team “is setting itself up for a spending spree in free agency—but also leaving themselves no other choice.”

If the stories are accurate, the Cubs have actually been dipping their big toe into the deep end of the free agent talent pool this offseason. They’ve reportedly made plays for Dylan Cease, Emilio Pagan, Pete Alonso, and Devin Williams while still, supposedly, being in the mix for Alex Bregman, Robert Suarez, Zac Gallen, and Japanese pitching import Tatsuya Imai.

The likely plan

MLB: San Diego Padres at Chicago Cubs
MLB: San Diego Padres at Chicago Cubs Apr 4, 2025; Chicago, Illinois, USA; Jed Hoyer President of the Chicago Cubs prepares to throw balls to fans before a game against the San Diego Padres at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

But, obviously, the front office won’t be looking to fill nine roster slots from the premium section of the free agent market. Reliever Phil Maton has, so far, been the Cubs’ biggest free agent pickup, coming aboard on a 2-year, $14.5 million deal. One would assume that a good chunk of the remaining roster slots will go to pitching, as Chicago is still in the process of rebuilding a bullpen drained by outgoing talent.

Most probably, the team will go “big” on one player, “biggish” with two players, and then fill the rest of the openings with fringe assets and bargain buys. Whatever the case, the Cubs’ roster will definitely get to around 40 before the start of spring training.

Where’s the homegrown talent?

Syndication: The Des Moines Register, Chicago Cubs, Owen Caissie
Syndication: The Des Moines Register Iowa Cubs’ Owen Caissie (17) makes his way to the dugout on Friday, March 28, 2025, at Principal Park in Des Moines. © Cody Scanlan/The Register / USA TODAY NETWORK via Imagn Images

Perhaps the bigger issue, however, is why the Cubs’ minor league system isn’t producing enough roster-ready talent to stock up the 40-man.

Brett Taylor of Bleacher Nation also touched on that point of interest:

“…It’s not necessarily a good thing to have so few players in your organization that have reached a point in their careers, and an ability level, where you have to place them on your 40-man roster. This is absolutely a reminder how things have quietly (but quickly) gotten a little dire down on the farm.”

The Cubs’ farm system has been top-heavy the last couple years, with much of the top talent sitting at the Triple-A level. As those players make the major league roster or leave the organization, they are not being replaced by rising talent. That’s a major issue that will impact the big league product in a few years.

For now, though, the Cubs’ wide open 40-man roster is a big opportunity that affords the front office with a crazy amount of flexibility. Expect lots of movement relatively soon.

The post Chicago Cubs set for a spending spree to restock depleted roster? appeared first on ChiCitySports.


Source: https://www.chicitysports.com/chicago-cubs-free-agents-winter-meetings-roster


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