Four Paths Cubs Could Take to Build 90-Win Team as They Embrace ‘Emotionless Strategy’

In their pursuit of sustainable competitiveness, the Cubs are moving further toward a model-based approach that favors data over scouting. Sahadev Sharma and Patrick Mooney went into great detail on the “rational, emotionless strategy” that some criticize as eschewing the organization’s financial might in favor of a small-market mentality. As anyone who’s been following the club for a while knows, however, Jed Hoyer has often expressed an affinity for the way teams like the Rays, Guardians, and, yes, even the Brewers do things.

That’s a big part of the reason Carter Hawkins was hired as GM after spending nearly a decade and a half in Cleveland’s front office. It was also a factor in handing David Ross a pink slip and making Craig Counsell the game’s highest-paid manager. Counsell, who spent time working with the front office before assuming the reins as manager, is perceived to have a more elevated view of overall baseball operations than his predecessor.

While there’s understandably going to be some pushback to this seemingly small-market strategy, particularly from those scouts whose livelihoods are impacted, it reminds me of what Theo Epstein did with the Red Sox and Cubs. He took a lot of what is now generalized as Moneyball and threw more resources at it than what the A’s were ever able to, creating a great deal more margin for error and, ideally, shortening the timeline between competitive peaks.

Most small-market teams have a finite window within which to compete, then they’ve got to trade off players before they get too expensive and start the cycle all over again. Organizations with massive revenue streams should theoretically be able to maintain that competitiveness by spending through mistakes, something the Cubs have stubbornly refused to do since about 2019 or so. And no, I’m not going to launch into yet another diatribe about how Bryce Harper should be playing on the North Side.

How the continuation of their model will play out into a future Hoyer and Hawkins may not even be involved in remains to be seen, though I get the sense it would take a disastrous result in 2025 for the pair not to be extended. With that in mind, I want to look more closely at how the Cubs can go about attacking this offseason to put them in position to generate what they hope will be the first of many 90-win seasons in a row.

Despite all the talk — and actual action — around using models to extract the best value, I do believe Hoyer is going to have to be more aggressive with his moves over the next few months in order to jumpstart the cycle. It’s pretty much like priming and choking the engine on your lawnmower, as long as Hoyer has the strength to pull the cord with enough force to get it to turn over. Then he’s got to turn off the choke, which you can feel free to take either figuratively or literally.

Anyway, here are four paths the Cubs could take this winter. Keep in mind that these are pretty binary on the surface.

Run it back, but lean heavy into pitching upgrades

As things currently sit, all nine regular position players (that includes DH) are back for at least the 2025 season. That means Hoyer has very little ability to affect significant upgrades via outside additions and will need to depend heavily on players outperforming their projections. We recently looked at how that’s possible based on more consistent offensive production, but the likelihood of getting multiple hitters to have career seasons is quite low.

Where the Cubs do have room for significant improvement, both in terms of depth and top-end potential, is the pitching staff. Does that sound odd given how well the unit performed as a whole? Maybe, but it’s their clearest avenue for improvement given the state of their primary hitters. I can see the front office targeting Max Fried, Shane Bieber, and/or Walker Buehler for the rotation while also looking to solidify the back end of the bullpen.

After years of treating the relief corps as more of an afterthought, it sounds like Hoyer is serious about investing more money on it this season. That means at least one multiyear deal and a higher-cost short-term contract or two. As I noted in an earlier piece, I could see them being interested in Carlos Estévez and Clay Holmes, both of whom have significant closing experience.

Even if they get the same exact production from the offense and similar collective performance from the starters, think about how many more wins the Cubs could get just by not blowing so many games late. This is a very passive approach on the surface, which is more in keeping with Hoyer’s pedigree, so perhaps we can turn the volume up a little.

Addition by subtraction

Cody Bellinger‘s decision to return removed a whole lot of flexibility, especially when it comes to calling up one or more of the top prospects who should be in Chicago quickly if not immediately. As such, Hoyer may want/need to shop his right fielder in order to clear payroll and roster space. The Yankees might be interested in a lefty-batting first baseman after declining their team option on Anthony Rizzo, and Bellinger’s power numbers would likely benefit from Yankee Stadium’s short porch.

The most popular name in trade proposals had been Nico Hoerner, but his recent forearm surgery should table that for the time being. Isaac Paredes is another possibility, especially knowing how his pull-heavy approach is hurt by Wrigley Field and other NL Central parks even if the weather isn’t as detrimental next season. If the Cubs are comfortable enough with Matt Shaw‘s ability to play third base — hell, look how much time they gave Christopher Morel — Paredes could be moved.

They could use Hoerner’s potential early absence as a trial run for Shaw before making any firm decisions.

Scorched earth, let the kids play

I don’t think there’s any way in hell this happens given it runs contrary to their desire to compete, but the Cubs could move Bellinger, Paredes, and Jameson Taillon. Then they could take diminished returns on Ian Happ and/or Seiya Suzuki just to get them to waive their no-trade clauses. Rather than trade for a veteran catcher to operate alongside or ahead of Miguel Amaya, they could promote Moises Ballesteros and let him learn on the fly behind the plate while his bat plays.

Shaw would play third, Owen Caissie and Kevin Alcántara would alternate between one of the corners and DH, and Cade Horton would take a spot in the rotation. James Triantos may need a little more time in Triple-A just to figure things out, but he can come up by midseason at the latest.

This would be the most fun option even if it’s detrimental to the team’s performance because at least we’d know they’re not really trying to win. Hoyer has created a maze for himself by building a team replete with good-not-great players who can’t readily be replaced by prospects that can definitively be said to represent an immediate upgrade. Over time, sure, but not right away in 2025 when a baseball boss on an expiring contract needs to win in a meaningful way.

Blockbuster trade for superstar

This is the one where the Cubs part with two of their top prospects and an MLB player to acquire a middle-of-the-order bat who puts butts in seats and baseballs in the bleachers. The most obvious name here is Vladimir Guerrero Jr. because he’s got the cachet to go along with the possibility of elevating the team offensively. You figure Triantos, Michael Busch, Alexander Canario, and someone else would be in play for such a deal.

Guerrero has just one year of club control and could earn close to $30 million via arbitration, though, so that increases the risk. What about targeting Brent Rooker, who isn’t a free agent until 2028? He’s entering his age-30 season and has hit 69 (nice!) homers over the last two years, giving the Cubs a massive power upgrade from the right side. He’s almost exclusively a DH at this point, so something would have to be done on the Suzuki/Bellinger front to accommodate him, but the pop is legit.

I think the most likely course of action is something between the first two paths, with a milder version of the fourth thrown in. The Cubs are almost certain to prioritize pitching and they have to make a little room for some of their top prospects, but they can’t accommodate everyone from the farm system. After all, prospects exist to either contribute to the big club directly or to be traded for players who can.

Let’s hear your predictions for how the Cubs will proceed in the coming weeks, whether it’s specific free agent and trade targets or general philosophies. Have at it.