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Winter Meetings preview: 4 Cubs storylines to keep an eye on

Ryan Herrera Avatar
December 3, 2023

The baseball offseason stove is about to really heat up. With the Winter Meetings beginning in Nashville, Tenn., on Monday, rumors will be swirling around the clock.

An assortment of team personnel, agents, Major League Baseball employees, media members and more will group together at the Gaylord Opryland Resort, turning the Music City into the center of the baseball world for a few days. That’s good for the Cubs, who — in hopes of having an aggressive offseason — will benefit from having everyone they need to talk to all in one pace.

But what exactly will this year’s Winter Meetings mean for the North Siders? Will they bring in any of the top free agents? Is a splash trade on the horizon?

Here are four storylines to monitor as the meetings commence.

Will they bring in Shohei Ohtani?

The baseball world has been eagerly waiting for Ohtani to make his decision.

Though there’s some disagreement on when exactly that might come, plenty of rumors out there have claimed Ohtani will be ready to make his decision sometime in the near future, potentially even at the Winter Meetings. Whether that would work in the Cubs’ favor or not is anyone’s guess, but at the very least, getting an answer sooner rather than later would be ideal.

The last time they recruited Ohtani six years ago, the Cubs were one of seven finalists and felt very good about their chances, even though the front office was aware of where they were disadvantaged. This time, the Cubs continue to be at the forefront of rumors surrounding Ohtani, even being looked at among the favorites to land his services.

This is a franchise-altering move, and not just because of what Ohtani can bring in an on-field sense.

The New York Post’s Jon Heyman reported Sunday that Ohtani ” is believed to already have received multiple bids well north of $500 million, and some speculate he could even wind up as baseball’s first $600 million man — or come close, at least.” It’s an investment that, while it will surely bring in some level of revenue that helps offset the steep cost, it still will be a hefty price to pay on an annual basis. This wouldn’t seem to be president of baseball operations Jed Hoyer’s usual path if he wasn’t absolutely sure in Ohtani’s ability to keep the organization on an upward trajectory.

Obviously, Ohtani has proven what he can bring to the Cubs if they are to reel him in. He’s one of the best hitters on the planet, and despite elbow surgery in September, he’s expected to be good to hit on Opening Day. He won’t pitch in 2024 and there are legitimate concerns about his pitching future, but it doesn’t seem like that has scared off any potential suitors.

Will the Cubs get to the finish line with Ohtani? That remains to be seen, but it will be the biggest story for the Cubs this week in Nashville.

How will they address the rotation?

Hoyer was a bit shocked when Marcus Stroman opted out of the last year of his contract, but only because he wasn’t sure which way Stroman was leaning. But after Stroman made his decision, one thing became very clear — the Cubs need to add to their rotation.

At this point, Justin Steele (fresh off a fifth-place finish in NL Cy Young voting), Kyle Hendricks and Jameson Taillon figure to be rotation locks. In-house options for the other two starting spots include Javier Assad, Jordan Wicks, Drew Smyly and Hayden Wesneski. Even Ben Brown, who has yet to make his major league debut but owns a 40-man roster spot, could find his way into the big leagues quickly, and top-pitching-prospect Cade Horton may be ready to go at some point in 2024.

Hoyer said the Cubs are looking to give some of those arms an opportunity, but the fact is that they need more. And more specifically, they need more arms that can provide top-of-the-rotation type innings.

The free-agent market has some intriguing options. NL Cy Young winner Blake Snell and Jordan Montgomery remain on the board. Japanese ace Yoshinobu Yamamoto still has about a month left in his posting window, and the Cubs have been involved in rumors regarding his recruitment.

And then there’s the trade market. As far as rumored trade candidates go, Tyler Glasnow (Rays), Shane Bieber (Guardians), Dylan Cease (White Sox) and Corbin Burnes are higher-tier arms that could be on the move. Though the price to acquire any of them varies, all have potential to produce like No. 1 starting pitchers.

Obviously, for the Cubs to really improve their rotation for 2024, it’s going to cost either money or prospect capital. Their farm system is not currently producing major league starters who can help carry this team to the playoffs. It could get there eventually, but right now, they need to be aggressive in the pitching market. It would make sense to really get the ball going at the Winter Meetings.

Sep 27, 2023; Boston, Massachusetts, USA; Tampa Bay Rays starting pitcher Tyler Glasnow (20) pitches against the Boston Red Sox during the first inning at Fenway Park. Mandatory Credit: Brian Fluharty-USA TODAY Sports

Is a reunion with Cody Bellinger still possible?

At last year’s Winter Meetings, the Cubs got Cody Bellinger to agree to come to Chicago. A year later, it’s still unclear if his time at Wrigley Field is done.

Bellinger is among the top free agents on the position player side. After his bounce-back 2023 season with the Cubs, it would make sense for both sides to want to continue their partnership. But as of now, it doesn’t seem the two sides have made any headway on a long-term deal.

Not that it’s a surprise. If the Cubs are zeroed in on Ohtani as their No. 1 target, it makes sense to have that recruitment be their main focus. And on the flip side, considering how much Ohtani’s free agency is holding up a portion of MLB teams’ offseasons, it makes sense for Bellinger to let Ohtani set the market and then go from there. Having Scott Boras as his agent would make that the likelier scenario, and if history is any indication, Bellinger’s free agency could extend far past the Winter Meetings.

A few things would hinder a potential reunion. The Cubs signing Ohtani would seem to take them out of the Bellinger sweepstakes, just based on the cost and other roster needs. There’s also the idea that a team desperate to add one of the best bats on the market would potentially overpay, and a bidding war for Bellinger doesn’t seem like something Hoyer would be very interested in.

So yeah, Bellinger most likely isn’t signing a contract at the Winter Meetings. But with the baseball world in town, expect him to be among the most talked about names in Nashville.

Chicago Cubs first baseman Cody Bellinger (24) high fives teammates after hitting a solo home run in the third inning against the Cincinnati Reds at Great American Ball Park.
Sep 1, 2023; Cincinnati, Ohio, USA; Chicago Cubs first baseman Cody Bellinger (24) high fives teammates after hitting a solo home run in the third inning against the Cincinnati Reds at Great American Ball Park. Mandatory Credit: Katie Stratman-USA TODAY Sports

How else can they add power to the lineup?

Despite having six players hit 20 home runs in the same season for just the third time in franchise history, the Cubs were much more in the middle of the pack (or worse) in various power numbers in 2023. If their aspirations are really as high as the team’s brass says they are, then improving on that is of utmost importance.

Losing Bellinger, tied for the team lead in home runs last season, doesn’t help in that, and even re-signing him would just be evening things out, really. Ohtani would be a massive upgrade (124 homers over the last three seasons, fourth most in the majors in that span), but even then, it might still feel like they’d need more.

So who else is out there that could upgrade the slugging department?

As far as trades go, Juan Soto (Padres) and Pete Alonso (Mets) are possibilities (though rumors connecting them and the Cubs have cooled in recently). On the free-agent market, Ohtani and Bellinger are clearly at the top, but Rhys Hoskins is another pretty intriguing option.

Hoskins missed 2023 with a torn ACL, and Boras (Hoskins’ agent, too) has indicated a pillow contract similar to Bellinger’s could be in play. The former Phillies first baseman has hit at least 27 home runs in each of his four full season (twice hitting 30-plus), so while he may not put up monster power numbers, taking a shot to let Hoskins re-establish his value could very well be worth it for the Cubs.

Oct 14, 2022; Philadelphia, Pennsylvania, USA; Philadelphia Phillies first baseman Rhys Hoskins celebrates after hitting a three-run home run against the Atlanta Braves during the 3rd inning in game three of the NLDS for the 2022 MLB Playoffs at Citizens Bank Park. Mandatory Credit: Bill Streicher-USA TODAY Sports

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