Throughout the long and colorful history of Chicago’s National League ballclub, there have been some downright terrible times to be a Cubs fan. In fact, it’s not much of a stretch to argue that any random season drawn from a hat would produce more groans than smiles. But isn’t that kind of at the core of our fandom?
Given how long the Cubs have been around, they’ve given us plenty of reasons to ask why we put ourselves through this annual rite of masochism. But in most of those cases, we knew heading into the season that they were going to be bad. Dropping nine straight and 10 of their last 12 was just…ouch.
The wounds from the 2019 season are still fresh, and the Cardinals playing in their first NLCS since 2014 rubs a little salt in it. The Brewers finishing ahead of the Cubs for the second consecutive season squeezes lemon juice on the whole mess, while the departure of Joe Maddon and the realization of potential big changes creates an existential crisis of sorts.
Rather than gloss over all that went wrong over the previous several months, it’s time to really get in there and scrub those wounds clean. Maybe then we can move on, or maybe we’ll just end up feeling awful all over again.
And so it is that I present to you, Dear Reader, my estimation of the very worst losses of the Cubs’ 2019 season.
6/2/19 — Cubs 1, Cardinals 2: Waino causes pain-o with dominant performance
The healing power of time may have wiped one of the season’s biggest duds of the year from your mind, but fear not, I’m here to put it back. Unlike some of the games to come, this snooze-fest lacked that killer hit by the opposition. Instead, it was a total slog throughout, as the Cubs were thoroughly and completely dominated by the once-but-no-longer-very-good Adam Wainwright.
It looked briefly like the Cubs would mount a late game comeback. With Anthony Rizzo at the plate and runners on base, Kolten Wong dashed those dreams by completing the kind of catch that might have made a less mature version of myself throw a TV remote across the room.
Even watching it now, I am genuinely surprised — and not just a little bit angry — that he caught that. The Cardinals went onto a 2-1 win, capping the second worst sweep that the Cubs would face at the hands of St. Louis in 2019.
6/18/19 — Cubs 1, White Sox 3: No joy from Eloy
Some losses suck on their own merit. Others suck because they promote narratives or storylines that you’d prefer not to think about. This toxic waste spill disguised as a baseball game represented the latter.
The Cubs took an early lead against the consistently ineffective Iván Nova before allowing themselves to be completely shut down. The game would go into the 8th inning before Eloy Jiménez, who — wait for it — once played in the Cubs system, took Pedro Strop deep to give the White Sox a lead that they wouldn’t relinquish.
You’ll be shocked to learn that many, many people viewed this as definitive proof that the deal that sent José Quintana to the Sox for Jiménez was in fact the stupidest thing to happen since the closing of Hot Doug’s.
7/3/19 — Cubs 5, Pirates 6: BS play leads to BS for Kimbrel
Oh no, now we’re starting to get to the back-breakers.
This list is ordered chronologically, but I’m not sure this one doesn’t stand up as the very worst loss of the year. Not only did it include a walkoff victory for the Pirates, it also featured one of the stupidest plays you’ll ever see on a baseball field.
It’s not surprising that said play was perpetrated by the same person who would go on to be demoted after admitting that he wasn’t familiar with the signs. Worst of all, he defended his decision after the game, saying that he was just “a little too far back” to get the runner at home.
Craig Kimbrel gave the Pirates a walk-off win just one batter later.
7/27/19 — Cubs 3, Brewers 5: Two blown saves in Cheesetown
It really can’t get much worse than the rare double blown save, can it?
It still doesn’t look like that ball should get out, does it?
8/15/19 — Cubs 5, Phillies 7: Harper walks off in grand fashion
Do you remember when it felt totally inevitable that Bryce Harper would be wearing a Cubs uniform in 2019? His dog’s name is Wrigley, his best friend is Kris Bryant, and it just seemed to make sense. You knew he was going to have a huge impact on the Cubs’ fortunes.
And you weren’t wrong!
In the words of Kato Kaelin, vomit vomit vomit puke!
9/10/19 — Cubs 8, Padres 9: Cishek walks the world
It wouldn’t be possible for this list to be complete without an entry from the season’s worst month, September. Among many sad affairs, the Steve Cishek walk game stood out.
Because there’s really nothing worse than a spirited comeback that falls just short and turns into a devastating loss, is there? That’s exactly what the Cubs got here. A three-run 8th inning tied the game at 8-8, but that scoreline wouldn’t last long.
The aforementioned Cishek allowed a single with one out. From there, he was inexplicably allowed to continue pitching as he walked three straight Padres to force in the winning run.
And there you have it. Whether you wholeheartedly support my particular selections, I hope you agree that I’ve picked some of the most gut-wrenching moments of a gut-wrenching season. For some reason, I thought it might be “fun” to write this article. Why? You’d have to ask the ghost of Ryan past, who is, apparently, an idiot.
Which of these was your least favorite game of the season, or were there others I missed? You know what though, maybe it’s best to just leave well enough alone on that front.