What went wrong?
Updated: Oct 4, 2019
For the first time in four years, we won't get to see the red, white, and blue bunting at Wrigley Field. We didn't know it at the time, but the last time 'Go Cubs Go' rang out into the Chicago night was September 16th. The Cubs were 2 games back with 12 to play, 7 against the St. Louis Cardinals. We had them right where we wanted them, except we didn't. The Cubs lost 10 of the next 12, missed the playoffs, and let their Hall of Fame manager leave. So, what in the hell happened?
Honestly, I don't think it was just one thing that led us here but rather death by a thousand cuts. Let's look into the three main areas that I think steered the runaway train that was the 2019 Cubs.
Roster Construction:
It's my personal opinion that the failure to replace Dexter Fowler's production at leadoff is the greatest single failure of the Cubs post 2016. Fowler posted an amazing .393 OBP for 2016. Like his leadoff homer in Game 7 of the World Series, Dexter Fowler clearly set the tone for the Cubs and its been sorely missed.
Let's look at the lead-off production from 2016-2019:

In a case of WHAT IF's Zobrist posted a .368OBP in 23 starts there and maybe if he was with the team all-season we're writing about a 5th straight postseason appearance. No one could have foreseen Ben's situation and we certainly do not hold him responsible in any way. Family is first, but it leads us to the second part of the roster issue, Depth. The Cubs had no depth and it showed. Centerfield and Second Base were offensive black holes, and the first half bullpen was even worse. That leads us directly into my second reason for the 2019 collapse.
Front Office Mistakes:
Following the offseason losses of Jesse Chavez and Justin Wilson the Cubs replaced them with Brad Brach, Tony Barnette, and Xavier Cedeno. On paper it was a solid plan, relief pitchers are volatile by their very nature. Most of the high priced arms end up faltering (see Wade Davis, Andrew Miller, Craig Kimbrell, etc), so grabbing a few, cheap intriguing arms made a LOT of sense, it just backfired spectacularly.

Lacking a bat since Fowler's departure, AND needing a backup shortstop (due to Russell's domestic violence case) the Cubs only got Daniel Descalso and some minor league filler.
Another big Front Office mistake was depending on the growth of young players to sustain and grow the offense. Happ, Almora, Russell, Montgomery, and Edwards Jr. all took massive steps backward.

Okay, so maybe Happ didn’t take a massive step backwards but he was in Iowa for most of the season.
You'd have a strong argument that their big roster additions are also a part of the problem as well. Quintana, Heyward, Morrow, and Darvish (before 2019 2nd half) all took significant resources to acquire and they've returned less than expected results. Finally, the unexpected struggles of Pedro Strop sealed the deal. At the beginning of the season, Pedro was BACK! His first 11 games produced 2.53ERA, .559 OPS against and 11k (vs 2 walks) in 10 1/3 innings. Once he got hurt it started a domino effect and the bullpen never truly got right again.
Joe:
I really hate to put any of this on him because he could only play the cards he was dealt. He gave Almora 80 starts,15 at leadoff, because he legitimately had no one better. (Sidenote: Almora should've been shut down after that Houston game. He wasn't the same after that) When guys like Robel Garcia, CarGo, Mark Zagunis, Jim Aducci, and hell even Nico Hoerner see starts during a Championship Run things have gone very wrong. It the same story in the bullpen as previously reliable arms became very unreliable and there was no good option. My only real gripe comes with hindsight, I wish Rizzo was moved to leadoff sooner. Having said all that, considering the transgressions listed above Joe had the team within 2 games of the Cardinals with 12 left to play (7 against the Cards). He managed his ass off this year but even he couldn't overcome the flawed roster he was given.
So, how do the Cubs attempt to fix everything? Well, even though there has been a Front Office shakeup already, they aren't going to fire themselves so that leaves Joe and the Roster. We already know Joe is gone and we expect there will be some significant roster changes before Opening Day. It's ironic that the Cubs offseason 'fix' is looking a lot like a Meatloaf, because that was a specific point of contention for the club in 2019. I could write all night about this, but that ain't getting us nowhere. Let's just hope the new manager and roster changes are enough, two out of three ain't bad.