Cubs Named Among ‘Most Desperate’ Teams at Winter Meetings, Shohei Ohtani Decision Expected This Week

Repeating an otherwise powerful adjective over and over removes a great deal of its impact, so it doesn’t mean much when Bob Nightengale uses “desperate” five times in the preamble of his Winter Meetings preview. When it comes to the Cubs, however, it’s at least fair to say they’re very driven to follow through on Jed Hoyer’s stated desire to continue the momentum from their winning season. We can debate just how much momentum 83 wins really built, but their first big move of the offseason certainly spoke to aggressive plans.

“You don’t fire your beloved manager, steal manager Craig Counsell from your rival, pay him a record salary, shout from the Chicago rooftops that it’s Ohtani or bust, and sit back and tell your fanbase that at least you tried if you don’t land him,” Nightengale wrote. “Uh-uh. It’s not good enough. The Cubs have to go big, and at least win the NL Central, or heads will roll in their front office, too.”

For what it’s worth, Nightengale also listed the Padres, Dodgers, Blue Jays, Giants, and Yankees among the most desperate clubs heading into the Winter Meetings this week in Nashville. Four members of that group are finalists in the Shohei Ohtani sweepstakes, one is trying to make a big splash by trading for Juan Soto, and the other needs to slash payroll by trading Soto away. There’s also at least one mystery team in the hunt for Ohtani, because of course there is.

The very obvious reality here is that having so many teams pursuing the most coveted free agent in history means several are going to need to pivot in a big way once he makes his decision. That means the Cubs — and presumably all the other teams, but we don’t really care about any of them — are being forced to operate with at least two different plans, one that sees them landing Ohtani and another that sees them offsetting their disappointment.

Even landing the two-way superstar means still having to shore up the roster in other spots, so Hoyer isn’t putting all of his eggs in one basket. The Cubs should be in the market for two starters since Ohtani can’t pitch in 2024, plus they’ve got to address their corner infield spots. It would make sense for them to look at several one-year options like Tyler Glasnow, Shane Bieber, Justin Turner, and Rhys Hoskins in order to buy a little more time for prospects without adding more long-term dollars.

As for the non-Ohtani plan, well, it may not look all very different. That probably sounds odd on the surface, but this isn’t a situation in which Tom Ricketts has allocated a specific budget for Jed Hoyer to spend no matter what. While that would be the case in normal years, Ohtani is anything but normal. His singular star power is such that he alone is worth making the largest financial commitment in MLB history, so removing him from the equation naturally lowers the budget significantly.

I still believe the Cubs will spend plenty of money if and when Ohtani signs elsewhere, they just aren’t going to blow the whole world away. Depending on timing, losing out on the biggest fish could see them throwing a little more on the hook for Yoshinobu Yamamoto. Or maybe they’d be willing to be more aggressive in trying to bring Cody Bellinger back. It’s just such a big drop from Ohtani to the next tier of acquisitions in terms of both cash and cachet.

Nightengale doesn’t believe Ohtani will sign during the league summit in Nashville, though he said a decision is expected “certainly before the Christmas holidays.” Jon Morosi reports that it could happen “within the next week,” which is very welcome news to anyone who’s been following this saga. That means Hoyer may only need to keep those dozens of plates spinning for another few days as he explores myriad options for the fallout, hence the Cubs being connected to all manner of free agents and trade targets.

Before closing, I want to repeat once again for the folks in the back that signing Ohtani would not mean the Cubs are done for the winter. In fact, the willingness to spend that much on someone who wasn’t able to win in Anaheim even alongside another elite player is very clear evidence that Hoyer knows it’ll take a lot more work. At the same time, knowing Ohtani won’t be at full strength until at least 2025 means it’s not a matter of trying to build a World Series team in one year.

So are the Cubs desperate? Nah, they just know they need to take a big step forward out of mediocrity and they have to figure out how to do it soon.