Whatever Approach Cubs Take This Winter, They Can’t Afford to Miss Again

Tom Ricketts may not have come right out and shared the Cubs’ payroll target when he made the media rounds Wednesday, but he left little doubt about the greater strategy for 2020 and beyond. Behind the delicious irony of the chairman saying “you can’t really buy teams” just days after meeting with the IRS to answer questions about his family’s purchase of the Cubs from the Tribune company was a dose of reality about how he wants to operate moving forward.

The Cubs had one of the highest payrolls in baseball this past season, an estimated $240 million expenditure that was greater than any postseason participants. On top of that will come something in the neighborhood of $11 million in “dead-weight loss” from exceeding the first two levels of the competitive balance tax threshold. Some rich folks might like throwing money away for the hell of it, but Ricketts is clearly running the organization like an investment rather than the labor of love he initially made it out to be.

“Ultimately, it’s great to have the financial resources that we do,” Ricketts said. “It’s an advantage and there’s no doubt about it, but the real key is you have to develop players. You can’t really buy teams, you have to build them. I think everybody in baseball understands that, our guys know that.

“And we have to really just re-focus on drafting well and then working on a lot of newer analytics and newer strategies for developing players to get their maximum potential. And that’s really what our challenge is now looking forward.”

While not unique or even the least bit objectionable in that context, these statements followed others about the dangers of exceeding luxury tax thresholds. So with the Cubs already projected to be over the 2020 limit of $208 million before adding so much as an aging utility infielder or a bounce-back reliever, this could all be interpreted as saying we’re in for another quiet winter in Chicago. It could even mean that the Cubs won’t just be limited in their additions, but will look to actively shed salary.

That’s all well and good if you’re simply trying to get the most bang for your buck, not so much if the goal is to make immediate improvements. With full knowledge that huge contracts don’t necessarily yield more wins, it’s both faster and easier to buy those W’s than to grow them when you’re dealing with a limited timeframe.

Listen, I get that Ricketts and others have said that a team with the Cubs’ resources shouldn’t have fleeting windows of competitiveness, but that’s not the point. Rather than look at things hypothetically, it’s necessary to weigh the reality that both the core of the roster and the front office are under contract for just two more years. So unless you think Theo Epstein is cool with merely setting the table for his successor(s), you have to believe he’s trying to go for it in each of the next two years.

Well, I guess you could be of the opinion that the Cubs should punt in 2020 and push all-in the following year. Some may even be cool with yet another attempt to squeeze a title out of the status quo. And yes, there are actually those who’re in favor of razing the whole thing and rebuilding. That isn’t possible in two years and it’s not great for the massive investments ownership has made throughout Wrigleyville, but whatever.

No matter how you believe the Cubs should or will go about attacking this offseason, every possible strategy has one thing in common: They can’t afford to swing and miss. Last winter saw them choosing to bunt, poking haplessly at a couple of pitches before fouling another off for a strikeout. Actually, it’s more like lining one right back to the pitcher for an easy double play.

Uninspired low-risk signings failed to pay dividends, then became actively negative due to injury and underperformance. That was compounded by a lack of development and the front office’s failure to build a roster that was dynamic enough to adjust to a league that had shifted dramatically beneath their feet. It’s like they followed up The Last Crusade with Kingdom of the Crystal Skull, getting stuck between old and new with a concept that failed on both levels.

Whether they end up defying expectations by splurging on a big-time free agent or they trade away one or two of their young stars, even if they just improve around the fringes of the roster, the Cubs need to hit a home run. They need to win if they stay around the $208 million CBT threshold and they really need to win if they get back up closer to $250 million. That means doing more than just picking guys up because they’re cheap.

Beyond that, it means getting aggressive with some of their prospects and having those guys work out. Maybe that’s Nico Hoerner starting at second base and producing at a higher level than Addison Russell would have at 10 times the price. Or it could be letting Brailyn Marquez prove himself at the highest level if he dominates at Double-A. Signing Shogo Akiyama to play center and provide a contact bat wouldn’t hurt, either.

Like Jon Lester pitching with reduced velocity and less deception, the Cubs just don’t have much margin for error when it comes to their offseason moves. They don’t need to be perfect, just damn close. If they can find those right fits and have a few things break the right way, the exact amount of payroll shouldn’t matter.

Of course, it’ll be a helluva lot easier to get things right if they get a few extra stacks of high society to play with. But hey, maybe all it takes is a manager willing to have the hard conversations while holding players accountable to his “winning ways.” I guess we’ll find out soon enough.

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