After a less-than-stellar end to the 2023 season, the Chicago Cubs are going into the new year with a lot to prove.

While the dismissal of manager David Ross proved the Cubs’ front office is taking the team’s contention window seriously, new manager Craig Counsell can’t be the biggest signing they make this offseason.

Chicago lost ace Marcus Stroman when he opted out of the last year of his contract at the end of 2023, so they have a crucial spot to fill in their starting rotation. Left-hander Cody Bellinger also opted for free agency, making power in the batting lineup another top priority.

Still, the Cubs are yet to spend a single dollar in free agency this winter.

Free agent spending this winter, by team:

Dodgers: $717M
Phillies: $172M
Diamondbacks: $122M
Giants: $113M
Royals: $105M
Cardinals: $99M
Reds: $87M
Tigers: $42.75M
Braves: $30M
Rangers: $26.5M
Mets: $18M
White Sox: $16.75M
Orioles: $13M
Astros: $12M
Brewers: $10.25M
Angels:…

— Jeff Passan (@JeffPassan) December 17, 2023

There are still plenty of big names that would fill holes in Chicago’s roster, but having already missed out on Shohei Ohtani, Juan Soto and Tyler Glasnow, the team’s front office has work to do.

Can the Cubs Win Back Cody Bellinger?

After an underwhelming stint with the Los Angeles Dodgers, Bellinger reinvented himself with the Cubs last season, becoming an unexpected bright spot on an otherwise shaky offensive lineup. Still, is the apparent effectiveness of Chicago’s hitting coaches enough to make the NL Comeback Player of the Year re-sign for 2024?

On a one-year, $17.5 million “prove-it” contract in 2023, Bellinger slashed .307/.356/.525 with a career-topping 20 stolen bases, ranking fifth in the NL in slugging and sixth in OPS (.881). His 26 home runs, 97 RBI, and 153 hits were the best he’s recorded since 2019 and earned him a Silver Slugger Award, so it wasn’t particularly surprising when the 28-year-old declined his deal’s mutual option at the end of the season.

But it’s not over ’til it’s over, and a new agreement makes a lot of sense for both parties.

Without Bellinger, Chicago has no clear option for first base or even close to enough left-handed power in their batting lineup. Without the Cubs, Bellinger could easily fall back into his Dodgers-era mechanics and once again find himself struggling to prove he could hit water if he fell out of a boat.

Still, with ESPN’s Jesse Rogers reporting that Bellinger and his agent, Scott Boras, are looking for a contract well over $200 million, the Cubs will have to loosen the purse strings if they want to get a deal done.

Is Jordan Montgomery the Starting Rotation’s Missing Link?

Just a few months after being traded at the deadline by the St. Louis Cardinals, 30-year-old Jordan Montgomery took home his first World Series ring as part of the Texas Rangers’ unstoppable starting rotation. Now a free agent for the first time in his career, could the left-hander be just what Chicago needs?

In 32 regular-season starts between St. Louis and Texas in 2023, Montgomery posted a 3.20 ERA with a 1.19 WHIP and 166 strikeouts. He made six appearances (five starts) in the Rangers’ ultimately successful postseason campaign, recording an ERA of 2.90 and 17 strikeouts.

Without Stroman, the Cubs’ starting rotation is essentially being carried by Justin Steele, so Montgomery’s strong and reliable arm would slot in very nicely. Even with Blake Snell still on the market, Montgomery is one of the most consistent starting pitchers available in free agency and definitely the most likely to fit Chicago’s budget.

Still, the Cubs will have to move quickly if they don’t want to see yet another top free agent sign with a competitor.