I have a confession to make.
I’m cheating on the Chicago Cubs.
There. I said it.
I’m a little embarrassed. I feel slightly dirty. Somewhere, a Cubs flag may have just lowered itself to half-staff.
But after watching the Cubs basically forget they were supposed to show up for the postseason, I have decided to temporarily cross I-55, head to the South Side and send some of my baseball juju to the Chicago White Sox.
TEMPORARILY.
I need that word entered into the official record.
I’m not changing teams. I’m not buying a White Sox tattoo. I still bleed Cubbies Blue.
Think of this more as a brief October baseball affair.
And honestly?
The White Sox have earned it.
First, About Cubs…
I have said for years that pitching wins championships.
Maybe that comes from being a baseball purist. Maybe it comes from growing up loving the game when pitching, defense, moving runners and manufacturing runs mattered a little more.
Greg Maddux, aka The Professor, remains my favorite pitcher for a reason, if not my favorite player of all time.
The frustrating part about the 2026 Cubs is that they were actually fun to watch until September.
Their defense was outstanding. Their offense spent much of the season covering gaps and putting runs on the board. In fact, the Cubs finished with baseball’s highest-scoring offense and best defense.
Then October arrived.
Apparently the offense had other plans.
The Cubs lost 8-0 and 4-1 to San Diego and went home.
That’s three runs in two postseason games.
Actually, let me correct myself. That is one run in two postseason games. See? I’m apparently still trying to give them extra runs out of sympathy.
San Diego swept them, and just like that, a season with legitimate expectations ended before I could really settle into my postseason complaining.
Yes, pitching matters.
Yes, injuries mattered.
Yes, there will be plenty of time this winter to talk about the rotation, bullpen, roster construction, and what Cubs President Jed Hoyer does next.
But sometimes baseball is much simpler.
You have to show up.
The Cubs didn’t.
So what is a disappointed Cubs fan supposed to do with all this unused October baseball energy?
Apparently cheat.
Hello, South Side
I have been watching this White Sox team, and I have to admit something else:
They’re fun.
Really fun.
That might be the strangest sentence I have written about Chicago baseball in a while.
Think about where this organization has been.
The White Sox came into 2026 after three consecutive seasons with at least 100 losses. In 2024, they lost 121 games.
Now?
They’re still playing baseball in October.
Not only did they make the postseason, they just swept Houston and advanced to the American League Division Series against Cleveland. It was their first postseason series victory since 2005.
That is one darn good turnaround.
This is a young team playing with the kind of energy that makes baseball fun to watch.
Maybe that is what I like most about them.
Baseball has a funny way of doing that.
A team can look hopeless one year and become one of the best stories in baseball a couple of years later.
A team loaded with expectations can dominate offensively for six months and score one run when October arrives.
Baseball doesn’t care about your preseason predictions.
Or your feelings.
I have approximately 50 years of Cubs fandom that can confirm the second part.
So Yes, I’m Cheating
Until the White Sox postseason ends, I’m sending some baseball old-school vibes toward the South Side.
Go ahead.
Judge me.
I can take it.
Cubs fans, consider this a temporary separation rather than grounds for divorce.
I’ll come back.
Probably.
Okay, definitely.
But right now, Chicago still has a baseball team playing meaningful games in October, and I want to enjoy the ride.
Besides, I spent part of my childhood around Joliet.
Crossing I-55 feels almost natural.
Crossing baseball loyalties?
That requires a little more explanation.
Then Comes the Long Winter
When the White Sox run ends—whenever that happens—I’ll turn my attention back to the Bears.
Which, as any Chicago sports fan knows, is an entirely different form of emotional risk.
Then baseball’s collective bargaining negotiations will become one of the biggest stories of the offseason.
The current agreement expires December 1, and there are already significant differences between Major League Baseball and the players over the economics of the game.
As someone who remembers 1994?
Please.
No sequel.
Losing the World Series that year because of a labor dispute was enough for one lifetime.
For now, though, I’m not worrying about December.
I’m watching October baseball.
And apparently I’m rooting for the White Sox.
I cannot believe I just typed that.
So here is my question for Cubs fans:
Once my Cubs are out, am I really cheating if I cross I-55 for a little South Side October baseball?
You’re still here? You made it to the end. Thank you for spending a little time here. I appreciate it.
Northern Illinois roots. Finger Lakes perspective. Cubs bias fully intact.
I write about baseball, history, mobility, public policy, AI, personal stories, and the beautiful mess of being human. My mind bounces between Pete Rose, politics, Taylor Swift, transportation, memory, mistakes, and whatever else helps me make sense of the world.
Writing helps me slow that down.
Most of my work will stay free. If this piece meant something to you, a paid subscription helps support deeper research, longer pieces, and future projects I’m building with care.
Free or paid, I’m glad you’re here.