5 questions facing the Cubs in the offseason

This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

CHICAGO -- The Cubs looked poised to punch their ticket to the postseason in early September. One of the culprits behind the ballclub’s tumble out of the playoff picture in the last few weeks was a pesky D-backs squad that was a thorn in Chicago’s side.

The Cubs lost six of seven meetings with Arizona in the final month, finishing one win behind the D-backs in the standings. Now, the D-backs have the National League pennant and are facing the Rangers in the World Series, proving once again that anything can happen in the playoffs.

“We want to be able to have a team that can make the playoffs every year,” Cubs chairman Tom Ricketts said on the final day of the regular season. “There's a lot more upsets and a lot more surprises in baseball playoffs. And the key to consistency is to not build like a one-year super team, but to try to get to the playoffs as often as possible.

“And you do that by finding guys that you like, giving them extensions, solidifying your core and then trying to supplement them with guys from your system and the occasional free agent. And that's going to be our strategy going forward.”

With that in mind, here are five questions facing the Cubs in this important offseason:

1. Will the Cubs re-sign center fielder Cody Bellinger?

Keeping Bellinger should be at the top of the front office’s wishlist, but expect that process to play out deep into the winter months. After making the most of his one-year contract with Chicago, Bellinger (a client of agent Scott Boras) is poised for a well-earned blockbuster contract as a free agent.

This decision will have a domino effect on other aspects of the Cubs’ offseason, too.

Above all else, the Cubs need to make sure they add impact offense, if Bellinger takes his .881 OPS elsewhere. There is also the fact that Bellinger not only played a strong center field, but he also handled innings at first base (which was an offensive black hole otherwise for the Cubs in ‘23). Without Bellinger, the Cubs do have internal options (top prospect Pete Crow-Armstrong among them), but there is not a ready-made, surefire backup plan for center field or first base.

2. Do the Cubs need to add to the rotation?

After the World Series, the Cubs must decide whether to pick up an option on veteran Kyle Hendricks (that is the likely outcome, and an extension is also a possibility). Marcus Stroman will also be letting the Cubs know if he plans on opting out of his deal, or staying put for $21 million in ‘24.

If both Hendricks and Stroman are back, they’ll be in a rotation that has Justin Steele (a Cy Young contender in ‘23) and veteran Jameson Taillon (whose final two months were promising). Youngsters Javier Assad, Hayden Wesneski and Jordan Wicks are next on the depth chart, along with veteran Drew Smyly. Prospects like Ben Brown and Cade Horton, among others, are coming soon, too.

The Cubs’ internal starting pitching depth is the best it has looked on paper in a long time, but the old baseball adage is that there is never enough pitching. Even with its solid depth, Chicago will explore whether it makes sense to add to the Major League rotation. Bringing in at least one impact starter -- helping development timetables and depth for the rotation and bullpen -- seems like a no-brainer.

3. How will the Cubs address the bullpen?

There were points in the season when the Cubs’ relief corps was a real strength, but injuries and escalating workloads took a toll on the group down the stretch. Having Adbert Alzolay seize the closer’s role is a good starting point, but Chicago needs to add volume this offseason to prevent a similar breakdown in ‘24. There are some intriguing young arms on the rise, but manager David Ross prioritizes having some established veteran arms in the bullpen.

4. Where will Christopher Morel play in ‘24?

Morel, 24, has grown into a fan favorite and boasts plenty of pop. He launched 26 homers in 388 at-bats and authored one of the Cubs’ best moments of ‘23 with his walk-off shot against the White Sox. The Cubs need to determine if Morel’s valleys (31% strikeout rate) are worth the peaks (.508 slugging percentage), and where exactly he can fit and be trusted on the field beyond designated-hitter duties. It is possible Morel gets dangled as trade bait this winter as well.

5. How will the Cubs leverage their improved farm system?

In his season-end press conference, Cubs president of baseball operations Jed Hoyer emphasized that he did not want to view the team’s growing list of prospects only as “coins to go get Major Leaguers.” That does not mean dealing from the farm is off the table -- Chicago reeled in Jeimer Candelario at the Trade Deadline for a pair of highly touted prospects -- but expect the Cubs to balance holding on to their top prospects with using the system to bring in impact players.