Chicago Cubs: Flies in the ointment, asking ‘where did it all go wrong?’

An exhaustive history of the Chicago Cubs‘ misdeeds would be so long as to fly in the face of reason, so I’m going to take a flyer on that here and instead concern myself with some of the misplays and lowlights of upper management’s history of dropped pop flies, to tell the story of what exactly happened here.

William Golding would probably recognize the scenario.

The first maggot of wisdom therefore would be the Kris Bryant service time manipulation incident, during which the Cubs held Bryant back from his major-league debut until April 17, 2015, holding forth the specter of starting third baseman Mike Olt in order to have Bryant log less days than required for a full year of service.

In fact, they did this so well that Bryant logged exactly one day less than the required total. The then-rookie logged his complaint with the designated authorities, who first swept it under the tarp, and then denied his complaint had validity, when Bryant lost his case.

Bryant played it off sometimes, but it became apparent over time that Bryant had a little sour-grape taste – and who can blame him? Of course, the team had to keep him around during the period when the case was being decided, and then they won an additional year of control in the process.

When it became clear to the team that Bryant would not re-up, the Cubs traded him to the San Francisco Giants for pitcher Caleb Killian and outfielder Alexander Canario. Both are perfectly good young players that are just beginning to ascent the ladder to the big club. They’re not expected to have any impact in Chicago until 2024 or 2025.

Chicago Cubs: Some notable swings-and-misses from management

Hindsight, of course, is 20/20 at least, and from this vantage point, it’s easy to see the Cubs might have been better off letting Jason Heyward and his pool-noodle bat play somewhere else, and signing Bryce Harper when he became available.

His reportedly amazing locker room rah-rah speech in the 2016 World Series notwithstanding, Heyward has done little at the plate to justify the expense in the eyes of fans. He’s lost his way offensively, if ever he was on the right path, and has been untradeable for the lifetime of his deal. He catches flies readily, but he lacks swat.

In 2018, when Harper was getting ready to hit the market, Theo Epstein was talking about having enough money available to do things like signing Harper, a boyhood acquaintance of Bryant. But the word seemingly came down from upstairs, and he stopped talking that way. Harper went on to sign with the Philadelphia Phillies instead.

After all, the Cubs already had Yu Darvish, who had signed in 2018 and then stank so bad that he drew flies and catcalls. It seemed that Darvish was broken, and everyone and Junior Brown wanted him out of town pronto. His flies went out of the yard.

In 2019, he turned in a Cy Young-worthy season, and leveled off but still pitched well enough in 2020 that he seemed a keeper. This enhanced his value to the point that he was dealt to San Diego with his personal catcher, Victor Caratini, for alleged major-league pitcher Zach Davies plus four prospects: Owen Cassie, Ismael Mena, Reginald Preciado, and Yeison Santana, all of who have done well enough in the low minors but are years away from the Show.

Davies was one of the worst pitchers in the Majors, and won’t be seen in a Cubs uniform again. His flies went out of the yard with frequency, but his stuff stayed the same.

Chicago Cubs: Lack of development has crippled this organization

The Cubs like to push their high draft picks through the system. Bryant, Kyle Schwarber, Ian Happ, Nico Hoerner were all first-round picks that succeeded to varying degrees. College bats. Otherwise they rarely promote from within, as their long-term development has been horrific. David Bote is likely the best home-grown product so far – which is downright terrifying to admit.

Let’s don’t even talk any more about the pitching, which is beyond bad. The Cubs haven’t developed a rotation pitcher since… Carlos Zambrano? Let’s say Andrew Cashner, who was a both a starter and reliever during his career.

So what do we have so far? The organization can’t draft or develop pitching, can’t develop position players outside of (sometimes) first-round picks, are not especially good at identifying useful free agents and don’t like to cut their losses.

They are so bungled and mangled that Theo Epstein took a powder with a year left on his deal, and has gone on to work with Rob (the poor) Manfred in hopes of somehow saving baseball.

The grim specter of the Collective Bargaining Agreement hangs over everything, and there may not be a 2022 season. There’s no light to be blinded by. In fact, it looks like the Cubs are preparing for just that. These next two months are going to be a grim slog through stagnant muck. I feel like Roger looking at the pig head, and sucks to Piggy’s ass-mar.