Cubs Free Agency

Cubs free agency preview: The biggest questions facing the North Siders

The Cubs have missed the postseason in five of the last six seasons, and only played three total games in the 2018 and 2020 playoffs

CHICAGO, ILLINOIS – AUGUST 05: Cody Bellinger #24 of the Chicago Cubs looks towards the field after striking out in the sixth inning against the Minnesota Twins at Wrigley Field on August 05, 2024 in Chicago, Illinois. (Photo by Griffin Quinn/Getty Images)
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For the fourth consecutive season, the Chicago Cubs missed the playoffs in 2024, and the team will be looking to finally get over the hump and get back into October in the following campaign.

The biggest question, of course, is how will they get there?

To answer that, the subject needs to be broken down into a few separate pieces, and the team will have to address the future of a slew of key contributors.

Will Cody Bellinger be back with the Cubs?

Outfielder Cody Bellinger just wrapped up the first season of a three-year deal with the Cubs, hitting 18 home runs and driving in 78 RBI’s in 130 regular season games.

Bellinger came with a hefty price tag for 2024, making $27.5 million, but the big question will be whether or not he opts out of the remaining two years of his deal and hit the free agent market again.

If he opts out, he will get a buyout of $2.5 million, but more importantly for him he would be one of the top available outfielders, an attractive option for teams who aren’t going to bid on Juan Soto or who miss out on a player like Anthony Santander.

An exit would also give the Cubs a good amount of flexibility in free agency, and would also free up space for a player like an Owen Caissie or Kevin Alcantara to get more regular playing time.

What about Kyle Hendricks?

The final remaining player from the Cubs’ 2016 World Series-winning squad, Hendricks is set to become a free agent for the first time in his career after the conclusion of the 2024 season.

It was certainly an eventful year for Hendricks, who went 4-12 with a 5.92 ERA in 29 total appearances, but he also had several games down the stretch where he showcased his vintage form, including 7.1 shutout innings against the Reds and allowing just a solo home run to the Colorado Rockies at Coors Field on Sept. 15.

That being said, the Cubs are in all likelihood going to focus on the robust pool of available free agent pitchers this offseason to boost their rotation, and it’s not clear whether Hendricks will fit in those plans.

Will the team swing a big trade?

With the large number of Top-100 prospects the Cubs have, and the number of large contracts that would be difficult to move to accommodate those players, it’s entirely possible the team could use a couple of minor league assets to go out and make a big trade this offseason.

Players like Vlad Gurrerro Jr. and Mason Miller both seem like potential big-swing candidates, but it remains to be seen if the Cubs are willing to part with the assets required to get either.

The Cubs could also swing a trade involving an established player, though questions would definitely arise should they decide to part with a player like Justin Steele or Nico Hoerner, both of whom would be huge assets for a team trying to compete for a playoff spot.

What is the team’s biggest need?

Even with Miguel Amaya and Christian Bethancourt helping the Cubs’ offense in the latter stages of the season, one could easily make an argument that catcher is the team’s biggest lineup deficiency at the moment.

Adding a more established hitter for the designated hitter role could also be a fit, though the team did find some success with Seiya Suzuki in that role late in the season, with Bellinger slotting into right field and Pete Crow-Armstrong in center. That could give the team the ability to continue putting Suzuki in the DH spot while sliding Alcantara or Caissie into the mix in 2025.

Outside of lineup spots, the starting rotation could certainly use a boost, with players like Corbin Burnes and Blake Snell both potentially hitting the market. Pairing one of those pitchers with Steele and Shota Imanaga would have a massive impact on the rotation, and would make for a fearsome 1-2-3 punch for teams to deal with.

The bullpen, naturally, remains a concern, and while the team did find some success in integrating players like Porter Hodge into the mix, more arms are always on the menu.

Will the Cubs rely on prospects for 2025?

The Cubs ended the 2024 season with the top five-prospects in their system at Triple-A Iowa and called up Alcantara for the final week, so in all likelihood they’ll have a slew of players banging on the door of the big league roster next season.

One would figure that Cade Horton will find a role with the Cubs, with Matt Shaw and Caissie also being in the mix, but how are they going to fit all of these pieces into the roster that has several players locked into long-term deals?

Elevating Shaw to the MLB roster may ultimately require some creativity, with a trade of Hoerner a possibility to make that transition occur. Caissie and Alcantara could battle for playing time in right field if the team decides Suzuki should serve as a designated hitter, while a player like James Triantos may still be on the outside looking in.

Moises Ballesteros may also end up challenging for a roster spot, though if he can prove to be a serviceable presence behind the plate, he could find a role a bit more easily than the team’s other non-pitching prospects.

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