We recently asked whether Dodgers fans had a preference as to which playoff seed (between top and second) they preferred. Overwhelmingly, the easier path on paper looks to be through the second seed. For most of the year, no one would have questioned this logic. However, as September has unfolded, an interesting wrinkle has become possible, if unlikely, involving both Chicago baseball teams.
At first, I only noticed it with the White Sox, but as the Cubs have dropped five of seven games to the Milwaukee
Brewers over the past two weeks, all but conceding the NL Central to the Brewers, who clinched on September 15, a question now must be publicly asked.
What on Earth is happening in Chicago?
We’ll start with the moribund American League, which has looked mediocre, to be generous, for most of the year.
The Pope’s Baseball Team
Interestingly enough, there are scenarios where current American League division leaders Chicago and Houston end up watching the postseason from home if things go sideways over the next two weeks, adding to this essay’s theme of chaos.
While no one in these parts will bang on about the Astros season ending up in the trash can, a White Sox collapse would be a sour ending to what has otherwise been a fun story.
As is well known, the White Sox have been nothing short of a dumpster fire over the previous two seasons, setting the record for losses in the modern era in 2024. It’s said that every team is guaranteed to lose a third of its games and win a third of its games, and it’s the remaining third that tells the story.
If a team can’t even win its “guaranteed” third of games, that’s how you know you’ve sunk into baseball hell. What a time for some divine intervention, no?
It is still mind-boggling that the current Pontiff is both American and a lifelong White Sox’s fan. The White Sox have clutched on to this unexpected event with gusto, with both a mural of the Pope in Rate Field to commemorate the fact that he went to Game 1 of the 2005 World Series and an official miter giveaway day.
The 2026 White Sox are not what I would call a good team, but the turnaround is remarkable. When I first visited Rate Field, it was a drab and joyless experience, only made memorable by a decent chocolate milkshake.
Rate Field is still bad, but when the locals have something to cheer about, the facility is less drab.
The White Sox are the figurative C-student doing their best in a remedial class where all of their classmates are either going through issues at home (Minnesota), spectacularly underachieving (Kansas City, Detroit), or have skinflint parents (Cleveland). Accordingly, the White Sox have held the division lead since June and currently have the second seed in the American League.
However, the wheels have started to wobble and come off since the All-Star Break. As of the start of play on September 18, the White-Sox are 28-30 since the break, which is middle of the road, and 20-24 since August 1. As we recently covered, the Dodgers and White Sox have generally feasted on sub-500 opponents in 2026. The Dodgers have since rebounded against over-500 opponents, but the White Sox have started to lose to teams that a contending team should beat.
A final three-game series with then-second-place Cleveland just concluded with the White Sox falling out of the division lead for the first time since June. As the White Sox now are looking up at the Guardians, the precipice for flights to Cancun looms because the gaggle of mediocre teams clamoring for the sixth seed is right there, including Toronto, Texas, and, in the distance, Baltimore.
Yes, it would be the most Blue Jays thing ever for them to be basically unwatchable all year, having their fanbase whine that they should have won last year’s World Series, literally not be two games above .500 since the first week of the season, just to sneak into the sixth seed due to the sheer ineptitude of the American League.
Vlad Guerrero, Jr. hit his first home run at Rogers Centre on Game 150, which made the following near-miss from Game 7 even more darkly funny and emblematic.
The only way this scenario could get worse is if the Blue Jays end up in the ALCS, because they somehow waltz over the “happy-to-be-here” second-seed AL Central Winner.
Dodgers/Blue Jays 2: Poutine’d (Again)!, which would hopefully end in five games in Toronto with a third consecutive title, would be the sequel nobody wanted, but everybody in Los Angeles needed.
Yes, the American League has generally been a disappointment in 2026, but that fact should not obscure the renaissance happening in the South Side of Chicago.
Meanwhile, at Wrigley…
I understand losing to the Brewers in the regular season.
The Dodgers rolled over in spectacular fashion last year and in the home half of the matchup this year. Apparently, the Brewers changed their win song at the request of Manager Pat “Pocket Pancake” Murphy. I would not know, as the Dodgers took care of business while I was in attendance in 2026.
It happens, and when the Brewers are right, their brand of baseball makes most teams look slow and silly. Where most, including me, predicted that this year would be the year the Cubs finally won the NL Central, the Cubs were hell-bent on proving everyone wrong through what can be generously described as manic swings in quality of play.
Originally, I saw the Cubs start to wobble, but then over the last week, just about every lower seed but the Padres (really?!?) decided to go ice cold. For a split-second, I thought we might get both Chicago clubs staying home this October.
Now it just looks like potential heartbreak in the Southside and maximum chaos for the Wild Cards in the National League.
As of the start of play on September 18th, there is a 4-game gap between the fourth seed and going to Cancun.
- 4) Cubs – 85-68, +1 game over the sixth seed, 4-6 over their last ten
- 5) Phillies – 85-68, +1 game over the sixth seed, 5-5 over their last ten
- 6) Padres – 84-69, 9-1 over their last ten
- 7) Diamondbacks – 80-73, 4 games back of the sixth seed, 5-5 over their last ten
This essay started while trying to answer the question “Are the Cubs really going to cough it up?” Now, one must openly wonder whether the matchups we have considered a given for about a month are going to fall by the wayside.
Before anyone in San Diego starts preparing a coronation ceremony for the Padres, it’s helpful to remember who the Padres have played over their few series:
- New York Yankees (at home), 2-1
- Washington Nationals (at home), sweep
- San Francisco Giants (in SF), sweep
- Colorado Rockies (in Denver), 3-1
I see one decent test and ten games against opponents any playoff contender should win. (See also, the Seattle Mariners who somehow went 3-9 against the Sacramento Athletics and Anaheim Angels — yikes).
Whether we are witnessing the Cubs or Phillies slowly crashing out, or the Diamondbacks crashing in, will be resolved in the next week and a half.
Even while hoping for maximum chaos, Arizona needs to either find another gear or get some significant help from some mediocre also-rans while navigating the Yankees, Rockies (in Denver), and Padres (in San Diego). Yes, the Padres and Diamondbacks conclude the regular season by playing each other in San Diego.
The Padres play the Dodgers for their final road games of the regular season just before this showdown with Arizona, but that’s just one more element of this unfolding chaos.
