Cubs enter the new year with sights set on contending

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 -- By this point in the offseason a year ago, the Cubs had already held an introductory press conference for shortstop Dansby Swanson at Wrigley Field and announced the signings of Cody Bellinger and Jameson Taillon. The North Siders were one of Major League Baseball’s most active teams on the open market.

Outside of the hiring of manager Craig Counsell -- a move that stunned the baseball world -- things have been mostly quiet for Chicago so far this winter. The Cubs tried to lure superstar Shohei Ohtani to the North Side, but they have been left examining alternatives since his megadeal with the Dodgers.

“Winning the offseason is probably more curse than blessing,” Cubs president of baseball operations Jed Hoyer said at the end of the Winter Meetings in early December. “We'll just try to make the best decisions we can, and I think if we do that, we'll be in a good position.”

The arrival of the holiday season means Cubs Convention and Spring Training are nearly around the corner. There is still plenty of work left to be done as the Cubs try to build a playoff-ready team for 2024.

Biggest question to answer before Spring Training
Who plays center field?

The easy answer would be Bellinger, who was one of baseball’s best comeback stories in 2023. The issue, of course, is that Bellinger is arguably the top free-agent hitter available now that Ohtani is off the board. Bellinger is understandably seeking a hefty payday.

If Bellinger does not re-sign with the Cubs, the North Siders will have a puzzle to solve in center field. Chicago has center fielder Pete Crow-Armstrong -- MLB Pipeline’s No. 1 Cubs prospect and the No. 12 prospect overall -- but the club also does not want to rush him before he’s deemed ready. Mike Tauchman offers an experienced in-house option, and the Cubs could explore other short-term alternatives on the open market.

One player poised for a breakout season
LHP Jordan Wicks

When the Cubs picked Wicks in the first round of the 2021 MLB Draft, there was a strong belief that he was polished enough to move swiftly up the organizational ladder. The 24-year-old lefty lived up to that billing, reaching the Major League rotation in August in the thick of a playoff chase.

Wicks ended his campaign with a tough outing in Milwaukee (six runs in 1 2/3 innings) that skewed an otherwise strong MLB debut. In his first six starts, he went 4-1 with a 3.00 ERA, showing poise to go with a six-pitch repertoire that includes an elite changeup.

Prospect to watch in 2024
OF Pete Crow-Armstrong.

There are a handful of names to monitor closely for the upcoming season -- Cade Horton (MLB Pipeline’s No. 2 Cubs prospect), Ben Brown (No. 5) and Matt Shaw (No. 6), among them. With Opening Day in mind, however, Crow-Armstrong should be high on the radar and atop this list.

Crow-Armstrong got a taste of the Majors down the stretch in 2023, and he will likely compete for a spot on the Opening Day roster this spring. He brings elite defense and plus speed, but the Cubs will have to weigh whether their top prospect requires more development time at Triple-A Iowa before returning to the Majors.

One prediction for the new year
The Cubs will return to October baseball.

The North Siders were better underneath the hood last season than their 83-win finish would indicate. That is part of the reason why the Cubs made the surprising decision to hire Counsell. Hoyer felt Counsell could squeeze more out of Chicago’s roster, based on the manager’s track record in Milwaukee.

The offseason is far from finished and the Cubs still have multiple areas to address, but there is a solid foundation with a growing list of prospects climbing to the Majors. The Brewers look vulnerable at the top of the division, and Chicago may not be a World Series favorite, but there is definitely a path to returning to the October dance.