Ranking the Cubs' Biggest Offseason Needs After Wild Card Disaster

There is no easy way to put it: The Chicago Cubs failed.

They didn’t meet expectations, and it was a waste of a special season. The Cubs could be playing in the NLDS against the Milwaukee Brewers right now. But, to be frank, it would be an arduous challenge. Even if they did surpass the surging San-Diego Padres, the Brewers are a much different beast.

Their divisional foes are a team that hasn’t won a World Series but is always able to build a playoff threat every year. They're a team that continues to develop a solid farm system and churn out dependable talent every year. If the Cubs want to regain control of the division and make a deep playoff run, they need to take some notes from the team up north.

With that in mind, let's rank the organization's Top 3 needs heading into the 2027 season. I bet you can guess what is at the top of the list!

1. Starting Pitching

Oct 3, 2026; Los Angeles, California, USA; Los Angeles Dodgers pitcher Tarik Skubal (29) throws during the sixth inning of game one of the NLDS against the Atlanta Braves for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | IMAGN IMAGES via Reuters Connect

President of Baseball Operations Jed Hoyer was blunt at his season-ending press conference: Pitching is going to be the focal point of the off-season.

The Cubs will enter next season with many new guys, including most of the starting rotation. So many questions need answering. Will Justin Steele and Cade Horton return and make an immediate impact? Will the Cubs re-sign Shota Imanaga, Kevin Gausman, and Clay Holmes? What should the Cubs expect out of Edward Cabrera?

Even if the Cubs get all positive answers, the pitching will still lack a true No. 1 starter. Cade Horton has the potential to become that guy, but expect him to slowly but surely return to the high level he was at before the injury. So why not go after the No. 1 free agent this off-season?

Tarik Skubal was rumored to be traded at the deadline, and he was dealt to the Dodgers. He’s arguably the best pitcher in all of baseball. The Cubs will have a massive amount of cap space, but do they have a real shot at landing the superstar? It’s possible, as long as they're willing to get into a bidding war.

The Cubs signed Alex Bregman last year, and it did wonders for the team. Skubal would no doubt make the Cubs immediate World Series contenders. The contract will be tricky, but doable. Experts broke down the contract situation over on ESPN. The Cubs were not one of the teams mentioned in the article, but it’s hard not to look at the endless possibilities if he signs with the Cubs. The Cubs could potentially have a rotation led by Tarik Skubal and Cade Horton. Skubal, Horton, Steele, Gausman, and Holmes? The possibilities are endless in the minds of Cubs fans!

2. Bullpen

Sep 14, 2026; Phoenix, Arizona, USA; Miami Marlins pitcher Pete Fairbanks (29) throws in the ninth inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Matt Kartozian-Imagn Images | IMAGN IMAGES via Reuters Connect

The Achilles' heel of the Cubs was the bullpen — an endless rotation of guys who did not stay consistent. Jed Hoyer approached the bullpen as he usually does, but it did not pan out. He took flyers on numerous bullpen arms, including Holby Milner, Phil Maton, Jacob Webb, Hunter Harvey, Shelby Miller, and more. All either spent the majority of the year on the IL or struggled when it mattered most.

Hoyer at least blamed himself for the bullpen failures. But will he actually make the significant changes that need to occur, or will Hoyer rely on the same approach that he has used for the past few seasons? The Cubs need to target guys who can make a huge impact. It’s time for the Cubs to land several big-fish free agents. Raisel Iglesias of the Atlanta Braves, Pete Fairbanks of the Miami Marlins, and A.J. Minter of the Minnesota Twins are some names the Cubs should consider.

3. Catcher

With the Cubs expected to make major changes to their pitching staff, will they also revamp the catcher position?

Carson Kelly has a mutual option, but whether the Cubs will spend what it takes to retain him is unclear. Catching is an important skill to master, but it helps when a team has two or three reliable guys. Look at 2016, when the Cubs had a well-balanced catching group. Miguel Montero was the veteran left-handed hitter. Willson Contreras was the young up-and-comer. David Ross was the old grizzly leader. The Cubs should try to approach things with a similar mindset this offseason.

For instance, can the Cubs re-sign Kelly and call up top prospect Owen Ayers? A catching group of Kelly, Ayers, and Amaya gives the Cubs the depth they need. However, the Cubs can also try to upgrade the position. If the Cubs do not re-sign Kelly, options include Cincinnati Reds catcher Tyler Stephenson and Minnesota Twins catcher Ryan Jeffers.

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