When Will the Chicago Cubs Make a Big Move in Free Agency?

The Chicago Cubs have been quiet so far this winter. Will they soon make a move in free agency to become true contenders in the NL Central?

CHICAGO, IL - AUGUST 19: Cody Bellinger #24 of the Chicago Cubs watches the flight of a home run in a game against the Kansas City Royals at Wrigley Field on August 19, 2023 in Chicago, Illinois. (Photo by Matt Dirksen/Getty Images)

Since trading away their World Series core, the Chicago Cubs have not exactly executed a typical “rebuild”. Instead of striping the roster down to spare parts, the Cubs have stayed in the middle.

Signing proven big league talent to fair market deals has not resulted in a playoff appearance. So far, the Cubs have been rumored with big offseason names, but have yet to land an impact player.

The most obvious move would be bringing back Cody Bellinger. The former MVP saw a resurgence in his lone season with the Cubs slashing .307/.356/.525 with 26 home runs.

While a reunion is still possible, the Cubs could pivot to internal options, such as prospect Pete Crow-Armstrong, and allocate money elsewhere.

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Primary areas of need include starting pitcher, first base, and third base. Patrick Wisdom is still around and could man third or first, but we are all pretty familiar with his flaws and it might be time to move him off an everyday role.

Christopher Morel has been floated in every trade rumor, and rightfully so. The streaky power bat comes with control, versatility, and a 30% strikeout rate. If the Cubs do keep Morel, they will likely use him in a super utility role instead of cemented at one position.

The Cubs currently have $172,225,000 on the books for 2024. All indications point to their willingness to add more payroll. So, who could be the realistic options?

Starting Pitcher

Marcus Stroman coming back is on the table. He was productive in Chicago and spoke highly of the organization. Finding a comfortable number for both sides is still up in the air. Chicago has Ben Brown, Hayden Wesnenski, and Jordan Wicks as young rotation options with Justin Steele, Kyle Hendricks, and Jameson Taillon as the veterans. A need is there.

We know Chicago is never afraid of the big move and there’s a fit I think is perfect. Jordan Montgomery. Montgomery has been one of the most consistent, and even underrated pitchers, for the past few years. Many teams will be after him this year.

Yoshinobu Yamamoto has slowed the pitching market, and Montgomery’s market should pick up immediately after he is signed.

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Montgomery would be an excellent one-two punch with Steele and would stabilize a rotation for years to come. Chicago would be comfortable giving him a long term deal as his style of pitching should age well. I like the fit as a pitcher who produces a lot of groundballs landing with the Cubs who have a top notch defensive infield.

Third Base

Nick Madrigal at third should not even remotely be in the plans for 2024. If the Cubs land on Wisdom and Morel at third, so be it. However, I think they are going to look to upgrade. Maybe they go the trade route, but that gets costly quickly. Going out and getting someone like Isaac Paredes will not be cheap.

Instead, the Cubs pivot and sign Matt Chapman. Now, before we go much further, I personally do not think Chapman is some can’t miss, high level free agent. You can even argue he’s not enough of an upgrade from Wisdom to justify the contract. He brings power and an elite glove, which is the difference maker for me.

Chicago has valued defense and the opportunity to get one of the best gloves at third might be tough for them to pass up. I will note, Chapman’s power dipped hitting only 17 home runs but his 93.4 mph exit velocity, 17% barrel rate, and .457 xSLG points toward more power.

First Base

Last year the Cubs tried Eric Hosmer, Trey Mancini, and Matt Mervis at first. All were brutal, and Patrick Wisdom as the starter leaves much to be desired. Of course, how the Cubs view Mervis will ultimately determine what they will do at first, but I think it is time they bring in a more proven bat.

Welcome aboard, Rhys Hoskins. Hoskins has hit 25 or more home runs in each of the past four full seasons. Coming off an injury that robbed him of his 2023 season, Hoskins could look to take a shorter deal and hit free agency again once healthy. Chicago really could be a player in his market for a short term, or longer term deal making Mervis a trade candidate.

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Finding the answer at first has been an issue since Anthony Rizzo departed. Hoskins could be that answer and perhaps at a slight discount due to his injury. The issue would be too many righty hitters. Right now, Ian Happ (switch-hitter) is the only non-righty that’s clearly in the lineup on Opening Day.

Because of that, I would say one of either Chapman or Hoskins is more likely instead of both.

Either way, if Chicago added Montgomery and Hoskins/Chapman that is two big fixtures at two areas of need. That would be drastic upgrades from Mervis/Madrigal and the various unproven rotation options. Would this be enough to push the Cubs to the top of the NL Central? Time will tell.