Chicago Cubs: Winter Meetings open under shadow of payroll questions

The Winter Meetings have begun in San Diego and expectations have already been tampered when it comes to the Chicago Cubs and potential signings.

This time last year, we knew the Cubs weren’t about to blow anyone out of the water with a major signing. That didn’t stop us from dreaming of Bryce Harper or Manny Machado playing at the Friendly Confines, but we knew it would be minor tweaking and additions for a team coming off a 95-win season and a fourth straight postseason appearance.

Here we are, 12 months later in an even less desirable position. Chicago missed the postseason for the first time since 2014 and are in more of a financial bind than at any point in recent memory. A report from Ken Rosenthal of The Athletic (subscription required) 

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“Club officials are telling representatives of even low-budget free agents that they need to clear money before engaging in serious negotiations.”

Wonderful. That really puts this week’s Winter Meetings in a different light. While teams like the New York Yankees are willing to drop a quarter-billion dollars on the best free agent starting pitcher in years, the large-market Cubs are apparently ready to take an entirely different course of action this winter.

It’s not like Chicago doesn’t have needs. The starting rotation isn’t getting any younger. Center field and second base are big question marks, to say the least. First-year manager David Ross has a bullpen that, as it’s currently comprised, isn’t likely to inspire a lot of fans next season.

Instead, it’s looking more and more likely the team will have to shed payroll – likely in the form of someone like former NL MVP Kris Bryant – via trade before addressing any of those concerns. That’s a tough pill to swallow given the team’s recent run but it is what it is at this point.

I look at these payroll restrictions in a bit of a different light than most fans. I generally agree that the Ricketts family has a cash cow on their hands and being a major market club, should spend as such. The luxury tax implications matter very little to me this winter. But, it’s also not my money – so there’s that.

Then again, it’s not like Epstein and Jed Hoyer are batting 1.000 when it comes to big signings, either. Sure, the Ben Zobrist and Lester deals back in 2015 stand out as big wins. But Jason Heyward is yet to live up to his eight-year, $184 million mega-contract and guys like Yu Darvish and Tyler Chatwood have left plenty to be desired, as well. Let’s not forget that last year’s midseason signing of Craig Kimbrel didn’t exactly go as planned, either.

So knowing all that, it makes sense that Ricketts would want the Cubs to once again focus on drafting and prospect development rather than throwing tens of millions more dollars to fix evident holes in the roster. But in the meantime, you’re getting closer and closer to seeing your current competitive window (call it what you’d like) shut and your big-name talent hit free agency.

We’ll keep an eye on things this week – but it seems more and more like if the team does make a big splash in San Diego, it’ll be a move focused on the long-term success rather than a win-now play that puts all the chips on the table next season.