A Cubs-Focused MLB Winter Meetings Primer

Rumor Roundup
Shohei Ohtani - Perhaps the single most sought-after free agent in the history of the sport (even if his arm injury dampened the hype somewhat), Ohtani is playing his tour of interested teams extremely close to the vest. Rumors suggest that he'll actually punish teams who leak information about his meetings, though perhaps that plays into the Cubs' hands. Jed Hoyer and company have always been stealthy when it comes to transactions (see: Craig Counsell hiring). 

Right now, everything we know about Ohtani still suggests the Dodgers are the favorite (MLB insider Mark Feinsand even said that he'd take the Dodgers over the field when predicting Ohtani's next team), but the Cubs are a "serious threat to land him". He's undoubtedly the cog that's jamming the proverbial transaction machine right now, and once he decides where he'll ply his trade for the next decade, teams can begin to chart the rest of their offseason course.

Yoshinobu Yamamato/Shoto Imanaga - Two more Japanese icons are free agents this winter, though they're coming over via the posting system from the Nippon Professional Baseball League. Yamamoto is likely to receive a contract in excess of $200 million, while many experts are forecasting a contract similar to the one Kodai Senga got from the Mets last year for Imanaga. Yamamoto is probably going to be many teams' Plan 1-B to Ohtani's 1-A, though he should have a greater volume of interested teams thanks to his age (he's currently 25), his health (no major injuries or surgeries yet), and his contract demands (the total value of his contract is likely to be less than half of Ohtani's, even with the posting fee). Imanaga is older and less dominant, though he's just as much of a known quantity, with strikingly consistent results. He's in the Sonny Gray tier of starters and should not be considered a mere "consolation prize". 

The Cubs have been heavily connected to both, though Imanaga is a much more likely target regardless of if they strike out on Ohtani. If they do land Shohei, it remains to be seen if the Cubs would even be willing to play in Imanaga's expected average annual value range. 

Shane Bieber/Tyler Glasnow - The Cubs are known suitors of two of the available aces on the trade market, with the Rays a particular fit given their desire for a young, controllable starting pitcher who has already reached the major leagues. The Cubs have Hayden Wesneski, Javier Assad, and Jordan Wicks, who all fit that mold, though Wicks is probably too much for Glasnow alone. 

The Reds, Red Sox and Braves have also been commonly-mentioned pursuers of those hurlers, and teams with deep farm systems and pockets like the Yankees and Dodgers shouldn't be ruled out if the free-agent class shows them the cold shoulder. Each pitcher only has one year of control remaining: Glasnow has a $25 million salary in 2024, while Bieber is projected at $12 million in his final year of arbitration. An extension with either would likely be a priority for whoever snags them, but their proximity to free agency should drive the prospect cost to acquire them down. 

Team Needs:
Corner Infield - With Cody Bellinger and Jeimer Candelario both free agents--and both rumored not be priorities for the Cubs heading into the offseason--the Cubs desperately need to shore up what's been a problem spot on the roster since Anthony Rizzo and Kris Bryant were jettisoned two years ago. 

Players like Justin Turner, Brandon Belt, and Evan Longoria are long-established MLB veterans who can capably play either third or first base, on what would likely be a relatively cheap one-year deal. The Cubs can offer them a legit chance to play for a playoff contender. More glamorous options exist on the trade market, Pete Alonso and Alex Bregman chief among them. They’ve both reportedly been dangled ahead of their final year before hitting free agency, and the Cubs would love to add that kind of right-handed power to the middle of the lineup. It’s been reported that the Cubs will leverage the trade market to apply pressure to free agents, so these kinds of blockbuster deals (or a Juan Soto trade) will likely have to wait until the latter half of the offseason. 

Starting Pitcher - While the Cubs need a staff ace (hence their pursuits of Bieber, Glasnow, Imanaga, and Yamamoto), they'll probably look to sign a mid-rotation arm to replace the quality innings Marcus Stroman gave them over the last two years.

The market is deep with pitchers in this tier: Lucas Giolito, Frankie Montas, Jordan Montgomery, Jack Flaherty, Hyun Jin Ryu, and James Paxton are just a few of the names on the market. Obviously, not all of those pitchers are created equal (Montas missed all of last season with injury, for instance, while Montgomery was the de facto staff ace on the World Series-winning Rangers), but they’re all veterans with upside who shouldn’t command a contract on par with Blake Snell or Yamamoto. The Cubs do have a lot of young starting pitching depth, but they have to go into next season with more known quantities. 

Bullpen Help - Under the stewardship of Hoyer, the Cubs haven't been keen to dive into the deep end of the reliever free-agent pool. The last multi-year deal they gave to a reliever was Craig Kimbrel's infamous mid-season, three-year contract, and the last one they handed out during an offseason was to Brian Duensing in 2017 (which was only a two-year, $7-million contract). However, rumors have spread that the Cubs believe Counsell has a particular acumen for maximizing his relievers, and perhaps they'd be willing to shell out big money for the right guys. 

Josh Hader is probably going to be too big of a jump for the front office (despite his familiarity with Counsell), but the fact the Cubs are even being mentioned in his market is telling. Guys like Hector Neris, Jakob Junis, and old friends Andrew Chafin and David Robertson would be good fits and shouldn't break the bank. 

Third Catcher - It’s not going to be a priority for Hoyer or GM Carter Hawkins, but finding a solid, dependable third option behind the plate is paramount, especially since Yan Gomes is heading into his age-36 season. Mitch Garver is a name that’s been thrown around, but he’ll likely receive a contract that’s too rich for the Cubs’ blood, thanks to his bat. It’s more likely the Cubs sign someone closer to Spring Training on a minor-league deal, but don’t be surprised if they sneak a veteran catcher signing onto the transaction sheet in Tennessee. 

Miscellaneous Notes: 
Coaching Staff - There are still openings on Counsell's staff, though the bench coach role was just filled by Ryan Flaherty. It may not be as big of a priority as, say, Ohtani or Glasnow, but the longer the Cubs wait, the less likely they are to get their preferred options. They retained a lot of in-house coaching talent after the transition from David Ross, but getting a few more of "Counsell's guys" in the clubhouse would only help. 

Roster Crunch - The Cubs have 37 players currently on their 40-man roster, before any outside additions are made this offseason. Those three free slots will fill up quickly, after which the Cubs will have some difficult decisions to make on roster bubble guys like Patrick Wisdom and Nick Madrigal. Who gets designated for assignment or traded first will likely point to which positions the Cubs are being most aggressive on in trades and free agency. 

International Prospect Signings - The international signing period resets on December 15th. The Cubs reportedly signed four players with their remaining bonus pool money this year, and they are currently projected as the favorites to land top international prospect Fernando Cruz once the next window opens. 

Rule 5 Draft - The Cubs left a few players exposed for the Rule 5 Draft, including catcher Pablo Aliendo and pitcher Kohl Franklin, though none are particularly likely to be selected (and if they are, it’s possible they won’t meet the requirement of sticking on the drafting team’s major league roster for the full 2024 season). It’s also unlikely the Cubs will select anyone when their turn in the draft order arrives (they haven’t done so since they picked Trevor Megill in 2019), but it’s possible there’s a versatile bench bat or power arm they believe they can work with. Or maybe they’re still scarred from the famous under-the-table Josh Hamilton deal with the Reds. 

MLB Draft Lottery - For the second time, this event will lend some automatic fun and intrigue to the Meetings. The Cubs are most likely to pick 16th or 17th, but the lottery gives them a small chance to pick in the top six. The Nationals, who had a worse record than the Cubs last year and would theoretically have better lottery odds, are excluded from the process this year because they picked 2nd in 2023 and are revenue sharing payers. The Mets and Padres will both have their positions pushed back 10 picks because of their aggressive 2023 spending, and it's likely (though not guaranteed) that that pushes at least the Padres past the Cubs in any draft order. It would take extraordinary luck for the Cubs to pick in the top six, but some chance does exist.