Four Clear Questions Chicago Cubs Must Answer During MLB Offseason

The Chicago Cubs are staring at missing the playoffs again and these are just some of the issues they’ll have to address this offseason.

Nov 13, 2023; Chicago, Illinois, USA; Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell as new Cubs manager during a press conference in Chicago. / Kamil Krzaczynski-USA TODAY Sports

With every passing game, the Chicago Cubs are getting closer to missing the postseason once again.

The Cubs have not played a playoff game since the COVID-19 shortened 2020 season. Coming off an 83-79 season in 2023, Chicago has fallen short of its own expectations.

So, where does Chicago go from here? Whether the Cubs pull off a miracle and charge toward the playoffs or not, here are four clear questions Chicago will have to answer this offseason.

Closing Time

The Chicago Cubs ended the Hector Neris experiment earlier this week — and he led the team in saves with 17. Adbert Alzolay is out for the season after he had Tommy John surgery and likely won’t be back until 2026. He was the Cubs’ top closer in 2023.

So, yeah, Chicago needs a closer. Do the Cubs already have a closer? Is he in the minor leagues? Is he a pending free agent? Can they trade for one?

Chicago will need an answer to that question. It may be the most important question the Cubs need to answer to be a legit contender.  

The Cody Bellinger Question

If Cody Bellinger triggers the opt-out in his contract after the season, should the Cubs pursue him or let him go?

In 2023, he was named the NL Comeback Player of the Year. All it got him was a three-year deal with Chicago that featured two player options. If he stays, that’s $30 million on the books next season.

He isn’t having quite the season he had a year ago, but he could finish this year close to .300 with more than 20 home runs. That might be enough to prompt him to trigger that option.

If Bellinger goes, should the Cubs give chase? Will dealing with what will certainly be higher contract demands from Bellinger’s agent, Scott Boras, be worth the trouble? He’ll be one of the market’s top free agents once again.

Last offseason Chicago benefited from his soft market and didn’t have to overpay. The Cubs won’t get that lucky twice.

Managing the Coming Youth-quake

Who is ready and who isn’t to make their case for the 2025 Chicago Cubs? President of baseball operations Jed Hoyer and his staff will have to sort that out.

The Cubs’ top six prospects are ranked among the Top 100 prospects in baseball, according to MLB Pipeline. All six are at Triple-A Iowa — third baseman Matt Shaw, pitcher Cade Horton, outfielder Owen Caissie, catcher Moises Ballesteros, infielder James Triantos and outfielder Kevin Alcántara.

Within the next year, all six of these players could be ready to help Chicago at Wrigley. The Cubs expect Horton to compete for a spot, even though he’s out for the season with an injury.

Standing in the way is a Chicago roster in which the vast majority is either under long-term deals, in arbitration or in pre-arbitration. That’s good news for cost control, but bad news for prospects knocking on the door.

Will the Cubs allow them to develop at their own pace, push them to see who can help now or even use them to make the Major League team better via trade?

Justin Steele’s Future

Should Chicago spend the offseason trying to get left-hander Justin Steele into a team-friendly, long-term deal that bridges his arbitration years?

By the numbers, this certainly wasn’t the season Steele or the Cubs were hoping for. Injured for the first month, he is 3-5 in 20 starts. But, for the third straight year, he’s pointed toward an ERA just above 3.00 (3.10 as of Thursday). His strikeouts per nine innings is nearly the same as a year ago and his hits allowed per nine innings is down. So is his WHIP.

His 2023 wasn’t a fluke. This appears to be who Steele is. The longer Chicago waits to extend Steele through his arbitration years, the harder it will be to keep him at a reasonable cost.