A few months ago, a friend mentioned they were curious about when the Cubs would be good again. It’s a good question. We don’t know how long this rebuild will last.
It’s rather safe to say that this is not the year the Cubs will be actively “good.” They could make the playoffs. They could win the division. They could even make some noise in October. But the probability of them achieving a winning record is, per FanGraphs, less than 1-in-4, and the probability of them winning 90 games—an old baseline, from the recent good days—is much, much lower. More realistically, we’re looking at a point more distant than this season. Let’s do this year by year.
2023
Who’s still here:
- Seiya Suzuki
- Marcus Stroman
- Kyle Hendricks
- Nick Madrigal
- Jason Heyward
- Ian Happ
Who should be emerging:
- Brennen Davis (OF)
I’m limiting the first list above to expected key contributors, which excludes a lot of players, a few of them recently good. The reason for doing this is not to say those players won’t be good, but to say that you can’t count on them being good enough to hold down a roster spot. Patrick Wisdom is on the wrong side of 30. Frank Schwindel will be on the wrong side of 30 in a year. Nico Hoerner is full of question marks. These are the guys the Cubs are building around, and while we wouldn’t use that term to describe the situation with Jason Heyward, the Cubs are very much building around him, specifically around his $22M salary.
I’m limiting the second list to FanGraphs ranked prospects (top 116). Not all of these guys will pan out, but others who are not ranked will, making this a way to reflect, generally, what kinds of players will be emerging from the Cubs’ farm system in each of these next few years and what value they hold.
Altogether, the Cubs are committed to roughly $87M in salary for next year, a number that doesn’t include what they’ll pay arbitration-eligible players with MLB value, like Happ and Madrigal. To give this number some context, the Cubs are at around $127M this year in committed, non-arbitration-or-league-minimum salary, meaning that even if spending were to remain flat, they could go get something in the range of $40M worth of free agents. It’s a comparable haul to the Stroman-Suzuki combo this year, and at the median, it’s probably what to expect. The Cubs will beef up the rotation a little more, beef up the lineup a little more, and do other small things around the edges. Will it be enough to be good? I’m not sure. On paper, $40M is only worth five wins or so, but couple in Davis’s debut and expected improvements from Suzuki and Madrigal and you could have a decent team. Crucially, it might be close enough to a good team (and depending on what happens elsewhere in the division, the setting may be advantageous enough) for the Cubs to commit to more salary, which wouldn’t at all be surprising. The expectation should be, based on the Cubs’ spending history in the Ricketts era, that the Cubs will be near the top of the league in payroll when they’re ready to contend again. In short, being good in 2023 is a very real possibility, either due to strong growth from young players, an aggressive free agency period, a good start followed by an active trade deadline, or some combination of the three. On the other side of that, though, we might be looking at just a .500 year in 2023. The median is for a win total in the low-to-mid 80’s and wild card contention. That’s just the median, but that’s where it is.
2024
Who’s still here:
- Seiya Suzuki
- Marcus Stroman
- Kyle Hendricks?
- Nick Madrigal
- Brennen Davis
Who should be emerging:
- Kevin Alcantara (OF)
Kyle Hendricks’s 2024 option is vesting, and I don’t know the specifications on that, but the theme of this is that Suzuki is the new core, flanked by Stroman through ’24 and Madrigal through ’26. Madrigal is higher-risk than Suzuki or Stroman, but he’s the closest thing the Cubs have to a core piece aside from Suzuki, with hopes high on Davis but a lot of uncertainty remaining there.
Alcantara, acquired in the Anthony Rizzo trade, is currently expected to arrive in ’24, and now’s probably a good time to talk about the farm system. The farm system’s best assets are position players, yet again, and it’s a lot of high-upside, low-certainty pieces. The Cubs have a good farm system, but its strength is in its depth and its diversification, not in a collection of can’t-miss studs, like in the old days. They’re working on improving their pitching development, and that effort is bearing a little fruit, but it’s not showing up in broader evaluations of the farm just yet. Justin Steele looked great on Saturday, but that was one start.
Pivoting from that down note, though: The thing about 2024 is that the Cubs should have both 1) more free agent acquisitions and/or breakout guys forming a new core, from 2023, and 2) a lot of pressure on them to contend if they haven’t contended yet. If the Cubs don’t make the playoffs this year or next year, the drought will be three years long, and while that’s only half what it was at the end of the last teardown and rebuild, the Cubs are better-positioned for a quicker rebuild than they were in 2009, or even in 2012. Also, expectations have changed, and that matters. The expectation is that the Cubs will again one day soon be a powerhouse, and while that includes some down years (the Cubs are trying to be more like the Red Sox than the Yankees), it doesn’t include too many down years. Aggression should be expected prior to 2024 if 2022 and 2023 don’t work out.
The downside to this is that if 2023 doesn’t work out, and if it’s actively a bad situation, the gap the Cubs will have to cover to get to contention in 2024 will be larger, and building through free agency is risky (see: Heyward, Jason). For as fun as huge free agent signings are, the better scenario for the Cubs is to add five to ten wins a year these next three years, and to be adding free agents before 2024 to fill in holes rather than to form a core themselves. Win 80 games this year. Win 85 next year. Win 95 in 2024.
2025
Who’s still here:
- Seiya Suzuki
- Nick Madrigal
- Brennen Davis
- Kevin Alcantara
Who should be emerging:
- Owen Caissie (OF)
- Reginald Preciado (3B)
Remember Yu Darvish? He is Caissie and Preciado now, and a few others.
The Darvish trade stunk when it happened, but it stunk more because it signified a white flag than because it was a bad trade. It was a good trade, really. Not a trade we’d hoped the Cubs would be in a position to have to make, but a good trade given the situation in which they’d placed themselves.
Again, we don’t know if Davis, Alcantara, Caissie, and Preciado will be part of the core in three years. We can hope, though, that four current or soon-added minor leaguers will be part of the core, and these four are our current best guesses. If the rebuild isn’t going well at this point, the Cubs will likely be flailing in free agency and/or cleaning house in the front office, but realistically, it will probably be going at least decently well. Jed Hoyer is a smart man with a heck of a track record, with the Cubs and elsewhere, and again, spending should return to high levels, meaning two big free agent signings per offseason won’t be outlandish, especially with few clear big arbitration contracts on tap. By 2025 we could realistically be looking at a rotation with two homegrown arms and three mercenaries; a lineup anchored by Suzuki, Madrigal, Davis, Alcantara, and an acquired bopper; and a filthy bullpen of developed talent and aggressive short-term signings. Another 100-win Cubs team is not only possible in 2025, but it’s the center of the sights. A lot has to go right, and a lot has to be done right, but this franchise is in a very open position, with resources in the bank and a strong front office that’s rather transparently focusing on its biggest weaknesses, which are minor league pitching development and major league hitting development.
***
In total, there are probably three ways for this to go. The first is to go just as these last paragraphs had it mapped out: Contend for a Wild Card berth next year, contend for a division title in 2024, contend for a World Series in 2025 and enter a new window around the top of baseball. The second is to kind of scuffle and claw the whole way up there, potentially having to lean more heavily on free agent signings and trades but still getting to ’24 or ’25 with playoff expectations, just with a more fractured foundation and less certainty around them. The third is for this to fail—to sign more flops and to get none of the value out of the farm system that seems to lie within it. The first is likelier than the last two, but the last are real, which makes the titular question here a bit tricky. The shortest answer I can give would be, “2024.” The longest answer I can give is written out here. The best answer is, “Probably 2024, in terms of being a clear playoff team again. Hopefully from there it’s another blossoming, and this time one that doesn’t end up so firmly on the ash heap.” A great thing about having Hoyer running the show is that he did a lot of the running over the last one, and he was with Epstein all the way back in Boston. Hopefully, he’s a good learner.
