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Let’s Talk About the Cubs

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In which the author rambles on, nearly endlessly, about a team not covered by this blog.

Chicago Cubs v San Diego Padres Photo by Denis Poroy/Getty Images

Morning, all. Hope you’re having a fine Wednesday so far.

You know, over the past handful of years, one of the things which has increasingly grabbed more of my attention — and tended to show up very often in my writing as an overarching theme — is just how thin the margins are between success and failure. Or, more specifically, the lines between good and great, or good and average, and how quickly things can shift between those states. You’ve all been watching the same team I have over the past few years, and so I’m sure you understand from where my interest in this subject originates.

Over these past three seasons, we have witnessed the Cardinals hover in the land of good, but not quite good enough. It’s been frustrating, certainly. But for someone who tends to like zooming out and looking at the big picture in his writings, it has also been at least mildly fascinating. Seeing how a franchise attempts to cycle from one contending window to another, what forms the transitions take, and all the things that can go wrong and derail that process, is endlessly interesting, if also tough to watch at times when you just want to see a championship-level ballclub again, and not have to watch/think about/analyse the hows of getting there.

So let’s talk about the Cubs today.

The Cardinals are currently four games up on their rival to the North, heading out to Colorado for what feels like a trap series against a really bad Rockies team, while the Cubs are in San Diego, playing the excitingly disappointing Padres. A four game deficit is not insurmountable, of course, even with only 20 games left, and it’s entirely likely that the NL Central race will come down to the seven games (out of nine), that the Cards and Cubs play against each other to close out the season. And when the margin is close enough, and the games are all head to head, things can get crazy.

I say that to say this: what I am writing here is not meant to be elegiac in any way. As much as it will bring me pleasure when the Cardinals hopefully clinch the division, both because my tribe won and the tribe with whom we constantly war lost, I’m not trying to dance on anyone’s grave here. Rather, what I’m interested in is how thin the margin is between the dynasty the Cubs looked like they were kicking off in 2016 and the turbulent waters into which they appear to be heading now.

It is worth pointing out, of course, that it is not hard to imagine a situation in which the Cubs can climb right back into control of the division as soon as next season, and maybe the dynasty party is right back on. After all, while the Cubbies are facing down a four game deficit with less than two dozen games to go in the season, that difference in record comes down to differences in how each club has performed relative to their underlying numbers. The Cubs and Cardinals have identical Pythagorean records; the difference is that the Cubs are underperforming theirs largely due to bullpen issues, while the Cards’ bullpen has been airtight for most of the season, and they have been able to close out nearly all leads handed over. Swap a little luck or sequencing around, and the Cards could be tied with the Cubs, or even trailing by a few games, and neither team would have to be wildly out of the bounds of standard variation.

However, there is an increasingly noisome rumble surrounding the Chicago ballclub these days, and it’s not hard to see why. Three years ago, the fans on the North side were talking not just breaking curses, but winning multiple championships. Winning the division year after year, stepping on the collective neck of their longtime antagonists from Missouri, and basically establishing a reign of either perpetual bliss or perpetual terror, depending upon which side of the equation one happened to fall. And now, they’re facing a potentially very different situation going forward.

The roster is beginning to age, particularly on the pitching side. The Cubs’ primary five starting pitchers this year are 32, 29, 30, 35, and 35 years old, with Kyle Hendricks being the only one still in his twenties. The ridiculous young core of positional talent the Cubs built during the Theo Epstein teardown is still young, and mostly still very good, but they’re beginning to get not old, but expensive. Arbitration is starting to kick in for those players, and suddenly the core is no longer contributing 30 wins to the cause for peanuts. Javy Baez is only making $5.2 million this year, but will almost certainly get a huge raise this offseason, given he has a second place MVP finish on the resume and could garner some downballot votes again this year. Kris Bryant’s 2019 salary is just shy of $13 million, and that number is also due for a big bump, even as he has seen his production fall off from the MVP levels of his first couple seasons in the league. Willson Contreras will hit arbitration for the first time this offseason. Anthony Rizzo just turned 30 and has two options for 2020 and ‘21, both of which are very affordable at $14.5 million, but that’s not exactly peanuts, either. It’s more than Rizzo has ever made before, anyway. Jason Heyward and Yu Darvish are both under contract for four more seasons after this one, no matter what Al Yellon might think about renouncing their contracts to help out the team.

Opening Day payroll for the Cubs this year was just north of $200 million. That has bought them an 86-88 win club and a four-game deficit in the standings. It’s understandable there should be some consternation over the future of the club, particularly when there are so few reinforcements on the way. Yes, Nico Horner is a very good hitter, and an exciting player. He does not, however, fix a whole lot of problems on his own.

So how did we get here? This was not how things were supposed to go for the Cubs, the anointed National League counterpart to the Houston Astros as exemplars of the hard tank and rebuild as not only a viable strategy for success, but the defining strategy for creating a consistent winner in the modern environment of MLB. The Cubs were supposed to have three pennants by now, maybe two championships, and be working on a return to the Fall Classic here in 2019 with a cast of characters still almost entirely in the 20s. It is entirely possible, though certainly not a fait accompli, and maybe not even the most probable outcome, that the Cubs end up with a single championship and only one trip to the World Series out of this group built by the immensely traumatic process of a multi-year teardown and rebuild cycle. Again, not a guarantee — a few really smart moves, and maybe the Cubs see a rebound from Bryant, and hey, things are looking good again — but there are reasons to believe that the near-term future for the Cubbies resembles a storm front slowly rolling in, rather than the jersey-blue skies they believed was their destiny back in October of 2015.

Well, let’s start with that Bryant rebound thing. Truth is, Kris Bryant has basically rebounded to pretty much anyone’s idea of a star player. The 2018 season was a tough one for the star third baseman, but this year he has more or less performed as well as one could possibly expect. A .903 OPS, 134 wRC+, and 4.6 wins above replacement in 585 plate appearances is, frankly, awesome. Kris Bryant is awesome, and if the Cubs called tomorrow and said hey Aaron, we’ll give you Bryant for Nolan Gorman and anyone not named Carlson, I’d be sorely tempted to take that deal. That’s what kind of franchise-defining talent Kris Bryant is, even knowing he’s headed for a very large payday quite soon.

However, even as good as Bryant is and has been, he’s not been as good as he was at his best. He will likely end up in the neighbourhood of a five win season this year. That’s incredible. In 2016, though, when things looked like they were going to go the Cubs’ way for a long time, Bryant was worth 7.9 wins. The difference between Bryant, the fantastic 2019 version and Bryant, the surefire Hall of Fame 2016 version, is almost three wins. Those are FanGraphs numbers, by the way; if we go with the Baseball-Reference version of WAR, Bryant was a 7.4 win player in 2016, and a 3.5 win player this season. So almost a four win swing. And remember, Kris Bryant in 2016 was making right around league minimum and posting 7-8 wins, depending on the system you like. Kris Bryant in 2019 is posting 4-5 wins and costing $13 million.

Am I blaming Kris Bryant for the Cubs’ falloff this year? Absolutely not. What I’m doing is trying to illustrate that even when you’re lucky enough to have a player like Kris Bryant, you aren’t insulated completely from performances falling and taking a chunk out of your bottom line.

The real issue for the Cubs is actually three issues, all three of which are connected. One, Theo Epstein and Co. used up a whole lot of the rocket fuel they had on hand to try and bring home the franchise’s first championship in over a century. I can’t say that was a mistake, or that I would have done anything any differently; flags fly forever, after all, and even a Cardinal fan could see just how special that title was to one of sports’ most devoted fan bases. So I understand why they pushed so many of their chips in to the center of the table at the time.

The second issue is very similar to the first, but not exactly the same. This is the issue of how many further resources and assets the Cub organisation has burned through trying to keep the window of contention-slash-dominance open, rather than accepting the cost of that championship fuel burst as a couple years of cycling into some other players, rather than never missing a beat. Here I’m talking about the Jose Quintana deal. And the Yu Darvish contract. And maybe handing Craig Kimbrel a big contract for three years that covers ages 31-33.

Third is a different sort of problem, but still related. The first two have to do with the Cubs going all-in to win, which we Cardinal fans are perpetually frustrated by our chosen club’s unwillingness to do. There is certainly a commendable aspect to that willingness to throw caution to the wind and go for broke. But then again, there is another aspect to that willingness, and that is precisely what is going on with the Cubs right now. If you’re willing to go all-in, you have to be willing to live with having used up all your resources.

The last issue, however, has more to do with a failure, rather than a natural consequence. The Cubs’ front office has simply not done a great job of maximising their available talent, by which I mean they have not been as good at figuring out which players to keep as they were at accumulating all that talent in the first place.

Case in point: when the Cubs were trying to finalise their championship run roster back in 2016, they settled on the idea of trading for then and future Yankee closer Aroldis Chapman. It was widely reported at the time that the Yanks’ ask for Chapman centered around Kyle Schwarber, at the time rehabbing from a torn ACL which cost him almost the whole ‘16 season. He made an impact against the Cardinals in the 2015 playoffs, was hurt for 2016, and at the trade deadline that season was being looked at by the Yankees as a possible long-term fit at first base for them. Epstein balked, believing Schwarber was too much a part of the club’s long-term future, knee injury be damned. Instead, he sent Gleyber Torres, at the time the Cubs’ top infield prospect, to New York. Torres was only nineteen at the time, but had already shown off such precocious offensive ability from a middle infielder that future stardom was on the table.


Gleyber Torres has since blossomed into one of the best young players in baseball, posting roughly a four win season this year at just 22. His wRC+ is 131, and while he is a below-average shortstop by most measures, he’s not a complete disaster there. Certainly the aggregate production would have to be attractive to basically any team in baseball right now.

Schwarber, meanwhile, has settled in as a useful major leaguer, but really not much more than an average player. His career wRC+ in 1800 MLB plate appearances is 113, which is plenty good, but considering he’s down at the bad end of the defensive spectrum it’s not exactly crazy good. He’s actually been a really good left fielder by UZR, but plus/minus and DRS see him as being rather poor. It’s a weird split, and watching him I tend to go with the two that say he’s bad. He catches what he gets to, but he doesn’t get to that many balls. Torres has been worth about four wins this year, Schwarber about one and a half. That is not a great outcome.

Albert Almora and Ian Happ both had huge trade value at one point in time, Happ in particular. He was seen as a draft-day coup for the canny Cub cadre who drafted him out of the University of Cincinnati, and just the latest example of an organisation who made nothing but smart picks and smart decisions and were building the greatest offensive core anyone had ever seen. Almora’s OPS+ this season is 68, Happ’s is just 83. The Cub braintrust chose instead to move Eloy Jimenez, who was already a big-time prospect when traded at the 2017 deadline in exchange for Jose Quintana, but went supernova after being dealt to the White Sox, ascending to the very top of the prospect rankings, coming in with a consensus top three ranking prior to this season. Oh, and they threw in Dylan Cease, as well, who has yet to make an impact in the majors but came into the season sporting some of the most absurd strikeout stuff of any pitcher in the minors. (He was #25 on’s top 100 prospects this past offseason.)

Again, whoops. The Cubs recognised the limitations in Jimenez’s game, namely his below-average athleticism and poor defense, but didn’t seem to appreciate how bad Happ’s contact issues were in pro ball. They held on to Almora, believing the bat would be something it hadn’t really been at any point, and sent away their top pitching prospect instead.

Now here’s the thing: I can’t blame the Cubs for making the trade for Jose Quintana. From 2013-2017, Quintana was one of the most consistent producers in baseball. He was bad in 2018, but has been really good again this year. So Jose Quintana is not the problem, nor was his contract. But the Cubs gave up six years of control over Eloy Jimenez, along with six years of control of Dylan Cease, for Quintana. The real issue is that it was six years of two players whose values only increased after being dealt away, rather than a couple of the players who have basically tanked in the time since. Now Quintana is 30, will be 31 before the start of next season, and is a potential free agent. The Cubs hold a club option on him, which I have to assume they will exercise, because if not they have another big hole in their rotation to fill. And, since Dylan Cease is working through his command issues on the other side of Chicago, the Cubs are somewhat lacking in other options to immediately fill that potential hole.

It’s interesting to contrast the Cubs and the Astros, the other club who went down to the deepest depths of the sport, even deeper than the Cubs, in order to try and build a winner long term. When the Cubs arrived, they arrived all at once, and they immediately started throwing everything they could at first the problem of maximising their chance to win a title in 2016, then at the problem of staying on top, fighting off the Cardinals and Brewers, and not missing a beat. Their assets all came of age in one moment, and then the Cubs shipped off all the potential reinforcements, the Gleybers and Eloys of the world, to try and make the most of that one moment. In doing so, they absolutely did make the most of that moment, but they also basically made it infinitely harder for that moment to last.

The Astros, on the other hand, arrived as a contending club the same year the Cubs did, in 2015. They did not explode on the scene in quite the same way, admittedly; the Cubs went from a 73 win club in 2014 to a 97 win beast in 2015. The ‘Stros, meanwhile, went from 70-92 in ‘14 to 86-76 in 2015, with a somewhat more gradual rolling out of their future stars. And in fact, while the Cubs would attain even greater heights in 2016, the Astros actually took a step back that year, falling to 84 wins. The difference was that while the Cubs took their success and ran as far and fast as they could with it, Houston continued to bide its time, building up more and more and more of a foundation, trusting their pipeline to finish furnishing the core around which they needed to build.

The Cubs won in 2016 by emptying the nitrous tanks and pouring tons of assets into that championship run, then went even further to keep the good times rolling in 2017 and ‘18. The Astros won in 2017 by refusing to deviate from the plan when they got good then seemed to momentarily stall. Now, to be fair, perhaps had the Astros taken a big step forward in 2016, jumping into legit title contender status, they might have been tempted to spend more assets to try and push their window open immediately. Perhaps, in that way, Houston got lucky. They were able to stay disciplined because just when temptation might have come knocking too loudly to ignore, they were just a little bit too far away for it to grab them. Then again, maybe not. Maybe a 96 win season and championship dreams would not have changed the Astros’s approach at all. It’s tough to say.

Even when the time came to start adding big pieces to try and get over the top, the Astros were more measured and tactical than the Cubs. They did not give up their top prospect for two months of a closer. Houston did not throw money and prospects at every possible upgrade with a big name, either; instead, they made a couple of very notable, high-profile acquisitions, but managed to keep exactly the right players by targeting those assets they could get for just a little bit less than maybe the asking price could have, or should have, been. Perhaps the Greinke trade will ultimately look like the deal that cost the Astros too much. Perhaps not.

It is also only fair to acknowledge that the Cubs have been unlucky in ways the Astros have not been, or at least have not been just yet. Kris Bryant hurting his shoulder and not looking like quite the same level of player once he returned is a tough pill to swallow if you’re the Cubs. Three-plus wins of value missing is a pretty big deal. The Astros have dealt with some injuries, of course, but nothing that has limited any of their players longer term. That’s lucky, and that 100% helps. I’ve tried to communicate how much luck has affected the Cardinals’ fortunes over the past few years, but still there are those who always want to trot out the old homily about luck being the residue of design, and all that. There is some truth to that statement, of course, but there is also legitimate bad luck in the world, such as a top prospect who cannot keep his arm from breaking in one way or another every time he pitches, or another top prospect who made a very poor decision on a November evening almost five years ago now. Those are not excuses; they are things that happened, and have an effect.

Finally, look at the contracts the Astros and Cubs have each handed out. The Cubs have spent like a club at the very top of the market, throwing their financial muscle around with abandon. Houston, meanwhile, has brought in big-name players on big contracts, but they’ve also held back from ludicrous spending in favour of small, smart, marginal deals. The Cubs signed Yu Darvish, the Astros signed Wade Miley. That comparison tells you pretty much everything you need to know about how the two clubs have proceeded since each emerged from their respective rebuilds in 2015.

What has happened to the Cubs, what has likely shortened their window to the point they may no longer be the favourites in their own division, much less the dynastic force they were believed to be a few years ago, is complicated. All multifaceted issues like these are. But in another way, it’s not really that complicated. There’s some bad luck involved, certainly, in Bryant’s injury and diminished — though again, still awesome — production. In Happ and Almora both falling on their faces. In their bullpen this season managing to be fairly decent, except when they’re having hugely damaging blowups that cost games. But there are also poor decisions baked in, such as holding on to Schwarber so tightly and moving Eloy and Torres.

More than anything, though, what happened to the Cubs’ potential dynasty was that every decision and every move their front office has made since the Cubs got good in 2015 has essentially been geared toward propping the window open as wide as possible in the short and medium term, but shortening the time frame the window would remain open. The wave of reinforcements that would be arriving right around now to help extend that window are playing for other teams, mostly the Yankees and White Sox. In much the same way that the Cardinals have occasionally hurt the width of their window by refusing to ever allow it to close completely, the Cubs have shortened their window by kicking it open as wide as possible and demanding it stay there. Maybe they spend even more and make big moves this offseason and we’re right back to being terrified of the Cubs this time next year. But considering all the arbitration raises that are coming and how expensive that vaunted core is going to begin becoming soon, that may be too rich a task for even Chicago’s deep pockets.

The Cubs are still a good baseball team, and their best players are still very good indeed. But their window does not look unending now, and there are tough moves and decisions that will likely have to be made on the North side if they are going to reverse some of the more troubling trends which have crept in. In 2016, the Cubs looked like a dynasty. In 2019, they look like a very expensive 88 win team that needs help in some key areas they may have trouble addressing. In short, the smartest and greatest rebuild in the history of baseball has turned out to be smart, and pretty great, but not nearly so long-lasting as a lot of people thought just a couple seasons ago. And to me, at least, that’s really interesting. The margins really are awfully thin sometimes.