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Nov. 5: Will Cubs consider trade for Alonso, Soto?
The Cubs have said they would like to re-sign Cody Bellinger this winter. But if the open-market price for Bellinger becomes too exorbitant, Chicago might have to pivot elsewhere to fill a gigantic hole in its lineup. That could open the possibility for a trade involving a star hitter, such as the Mets’ Pete Alonso or the Padres’ Juan Soto.

According to Sahadev Sharma and Patrick Mooney of The Athletic (subscription required), a deal for either player “makes a lot of sense” for the Cubs. Both players are entering the final year of their contracts, meaning the asking price may not be too steep. Plus, it would allow Chicago to bulk up its offense while still having the resources to spend in free agency.

Whom might the Cubs have to deal in order to land one of those big bats? Sharma and Mooney think Christopher Morel is a name to keep in mind.

“Interested teams have already been doing their homework on Morel, a process that actually started at the Trade Deadline when several buyers scouted the Cubs as potential sellers,” they wrote.

The 24-year-old Morel hit 26 home runs last year and won’t be eligible for arbitration until 2026. However, he is one of the league’s more undisciplined hitters; he recorded a 31% strikeout rate and a 37% whiff rate last season. Although he played many defensive positions in 2023, it’s not clear if he excels at any particular one.

The Cubs might also have to dip into their farm system to make a deal work. A trade for Alonso may require the North Siders to give up one of their top pitching prospects to the pitching-needy Mets.

Nov. 4: As Bellinger, Stroman reach free agency, what will Cubs do?
Two of the Cubs’ most impactful players from the 2023 season are headed to free agency. Slugger Cody Bellinger declined his mutual option on Friday in wake of his resurgent year. Then, starting pitcher Marcus Stroman decided to opt out of the final year of his three-year deal Saturday, sources told MLB.com.

Well, no one is really off-limits for the Cubs. Two-way star Shohei Ohtani and Japanese ace right-hander Yoshinobu Yamamoto are considered the top free agents this offseason, and the Cubs may be in on each of them.

According to ESPN’s Alden Gonzalez (subscription required), the Cubs are among the 10 most likely suitors for Ohtani. Gonzalez writes that the Cubs aren’t afraid of going over the luxury-tax threshold, and even though Ohtani won’t pitch in 2024 following Tommy John surgery in September, the Cubs “might have enough young pitching on the way to let Ohtani take his time coming back on the mound,” he adds.

But Stroman’s possible departure does leave a pretty sizeable hole in Chicago’s rotation. That’s where Yamamoto comes in. The 25-year-old was phenomenal Saturday, striking out 14 batters in a complete game in Nippon Professional Baseball’s version of the World Series. Yamamoto, who has a 1.44 ERA across 550 2/3 innings over the past three years, is expected to be posted by his NPB club, the Orix Buffaloes, this offseason. The Cubs are one of the many clubs who have been linked to him, according to MLB Network insider Jon Heyman. 

While no one will get a more lucrative contract this winter than Ohtani, Yamamoto might end up signing the second-richest deal of the offseason. The Athletic’s Jim Bowden (subscription required) recently projected that his contract will be worth $211 million over seven years.

Oct. 28: Cubs reportedly interested in trade for Soto
On the heels of an active offseason in which they signed Dansby Swanson, Cody Bellinger and Jameson Taillon, the Cubs barely missed the playoffs in 2023, finishing one game out of the third NL Wild Card spot behind the eventual NL champion D-backs. Chicago figures to be busy again this offseason as it looks to take another step forward in 2024.

For starters, Bellinger is a free agent again. The Cubs are expected to try to re-sign the center fielder after he produced a .307 average, 26 homers, 20 steals and an .881 OPS over 130 games in a bounceback 2023 campaign. 

However, he might not be their only high-profile target. According to Bruce Levine of 670 The Score, the Cubs will be involved in the trade sweepstakes for Padres superstar outfielder Juan Soto. More >

Oct. 17: Re-signing Bellinger among Cubs’ priorities this offseason
Although they fizzled out down the stretch and ended up missing the postseason, 2023 was without a doubt a step forward for the Cubs, who bounced back from consecutive losing seasons to finish 83-79.

The performance was sparked by a successful offseason that saw the Cubs sign free agents Dansby Swanson and Cody Bellinger. What the team does for an encore could determine whether 2023 proves to be an aberration or the start of a multiyear contending window.

After signing a one-year deal last offseason, Bellinger is headed for free agency again. Re-signing him will likely be one of the Cubs’ top priorities, but there will surely be more competition for his services this time around after his stellar rebound season in 2023.

Addressing the bullpen, which faltered in September as the injuries piled up, is also a must for the club. The Cubs will probably look to add rotation help as well, especially if starter Marcus Stroman opts out. Justin Steele and Jameson Taillon are locks for their 2024 rotation, and Kyle Hendricks (club option) will likely join them. But the other two rotation spots are uncertain.