There are certain things in life you prepare yourself for. Disappointment. Heartbreak. Watching the Cubs strike out with runners in scoring position. The occasional season where you convince yourself that next year is our year before realizing you’ve said that 47 times in your life.
But this? The Milwaukee Brewers going to the World Series?
I wasn’t prepared for this.
I’m sad. I’m furious. I’m defeated. And somewhere deep down, I’m starting to wonder if the baseball gods have decided that watching Cubs fans suffer is their favorite pastime.
Because if you had told me three years ago that the Brewers would be on the doorstep of a World Series championship while Cubs fans sat around watching in disbelief, I would’ve laughed in your face.
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Not because I thought the Cubs were some unstoppable baseball dynasty. We’ve been through enough to know better. But because we finally thought we had the one thing that was going to change the balance of power in the National League Central.
We got Craig Counsell.
And for a brief, beautiful moment, it felt like everything was about to change.
We Got Craig Counsell. Surely, This Was the Turning Point.
When the Cubs hired Craig Counsell away from Milwaukee, it felt like a statement.
Here was the guy who had spent years managing the Brewers, winning the division, getting the better of the Cubs, and generally making life miserable for anyone who bled blue and red. He knew Milwaukee inside and out. He knew the division. He knew what made that team tick.
And now he was ours.
The guy who had been the face of the Brewers was coming to Chicago. Surely, that had to mean something.
The thought was simple: All right. Now we’re going to stick it to the Brewers.
We were going to take the guy who had been beating us and make him the reason we started beating them. We were going to turn the tables. We were going to finally stop watching Milwaukee act like it owned the NL Central.
It made sense in our heads. It felt right. It felt like the beginning of something.
Instead, here we are.
The Brewers aren’t just still good. They’re not just winning another division title. They’re not just finding another way to make the Cubs look up at them in the standings.
They’re going to the World Series.
Read that again.
The team we thought we were finally going to catch is now representing the National League on baseball’s biggest stage.
And I hate how much that hurts.
Milwaukee Owns This Division. And Now It Owns the National League.
For years, the Brewers have been that annoying team that just refuses to go away.
They don’t always have the biggest payroll. They don’t always get the national attention. They don’t always have the superstars that dominate the headlines.
But somehow, they keep winning.
They develop players. They find pitching. They make the right moves. They keep putting together teams that are good enough to beat you when it matters.
And as a Cubs fan, I’m tired of giving them credit.
I know they deserve it. That’s the worst part.
It would be so much easier if Milwaukee were a fluke. If they backed into the postseason. If they got lucky for a month and stumbled their way into a World Series appearance.
Then we could dismiss it. We could roll our eyes, call it a lucky run, and move on.
But when a team keeps winning, eventually you have to admit what you’re watching.
The Brewers have built something that works. They’ve made a habit of winning this division, and now they’ve reached the World Series.
Meanwhile, Cubs fans are left trying to figure out how the hell we ended up here.
We hired their manager. We thought we were making the move that would finally swing the rivalry in our favor.
And somehow, the Brewers are the ones celebrating.
It’s enough to make you want to throw your TV out the window.
The Craig Counsell Thing Still Doesn’t Sit Right With Me
Maybe this is unfair to Counsell. Maybe he needs more time. Maybe the Cubs will eventually get where we thought they were going when they handed him the keys.
I’m willing to entertain all of that.
But you have to understand what this feels like from the Cubs’ side.
We didn’t just hire some random manager with a good résumé. We hired the guy who had spent years tormenting us from the other dugout.
We took him away from Milwaukee and thought we were taking away a piece of what made the Brewers so successful.
It was supposed to be our move.
Our big moment.
Our chance to finally say, “You had your run. Now it’s our turn.”
Instead, Milwaukee keeps rolling, and now the Brewers have a chance to win a World Series while Cubs fans are left wondering when our turn is actually going to come.
There is something uniquely painful about watching the plan you convinced yourself was going to work unfold in the exact opposite way you imagined.
And the worst part? You can’t even fully blame Counsell for everything. Baseball is bigger than one manager. Rosters matter. Player development matters. Ownership matters. Execution matters.
But emotionally? As a Cubs fan?
I would really appreciate it if somebody could explain how this was supposed to make me feel better.
Because it doesn’t.
This Is What Defeat Feels Like
I can handle the Brewers being good for a year.
I can handle them winning a division title. I can even handle them having a playoff run where everything seems to go their way.
What I’m struggling with is the feeling that they’ve figured something out that we haven’t.
They keep finding ways to win. They keep putting themselves in position to make noise in October. And now they’re going to the World Series while we’re sitting here trying to make sense of it all.
It’s exhausting.
It’s exhausting to watch your rival celebrate the things you want for your own team. It’s exhausting to watch them experience the moments you imagined your team having. It’s exhausting to feel like every time you think the tide might be turning, Milwaukee finds another way to remind you that it isn’t.
And there’s no easy comeback for this one.
What are we supposed to say? That the Cubs will get them next year? That the Brewers are due for a fall? That our time is coming?
Maybe it is.
But right now, those words feel empty.
Because every Cubs fan knows the feeling of talking yourself into the future. You look at the roster. You look at the young players. You look at the moves the front office made. You convince yourself that the pieces are finally falling into place.
And then you look north, toward Milwaukee, and see the Brewers doing the very thing you hoped your team would do.
It’s hard not to feel defeated when the team you can’t stand keeps accomplishing the things you desperately want.
Ten Years Ago, We Were on Top of the World
And maybe that’s what makes all of this so damn frustrating. It’s not like Cubs fans haven’t experienced the mountaintop. We have. We know exactly what it feels like to watch our team win it all.
Ten years ago, in 2016, the Cubs were the team everyone was talking about. We won the NLCS, punched our ticket to the World Series, and eventually did the impossible. We ended 108 years of heartbreak and brought a championship back to Chicago. We watched the final out, celebrated in the streets, and convinced ourselves that maybe this was the beginning of something special.
Who would’ve thought we’d be here ten years later?
Who would’ve thought that a decade after one of the greatest seasons in baseball history, we’d be sitting here watching the Brewers (THE BREWERS) heading to the World Series while we’re left wondering when the Cubs are going to get back to that level?
Back then, Milwaukee was the team we expected to chase us. We were the ones with the championship, the momentum, and the feeling that we had finally figured it out. We had the parade. We had the memories. We had the bragging rights.
And now? The Brewers are the ones writing the next chapter of baseball history, while Cubs fans are left looking backward at 2016 and wondering how we got so far away from that feeling.
That’s the cruel thing about sports. You can spend a lifetime waiting for one championship, finally get it, and then spend the next decade chasing that feeling all over again.
I know what the Cubs gave us in 2016. I’ll never take that away from them. But I also can’t help thinking that ten years ago, if someone had told me Milwaukee would dominate this division and represent the National League in the World Series, I’d have thought they were out of their mind.
Now here we are.
The Cubs gave us the greatest baseball moment of our lives, and somehow the Brewers have managed to make being a Cubs fan feel miserable all over again.
The Worst Part Is That I Have to Live With This
If the Brewers win the World Series, we’ll never hear the end of it.
And honestly, why should we?
They’ll have earned the right to talk. Their fans will have every reason to celebrate. They’ll get to enjoy the greatest moment in their franchise’s history, and Cubs fans will have to sit there and take it.
We’ll hear about how Milwaukee built its team. We’ll hear about how the Cubs hired Counsell and still couldn’t stop the Brewers. We’ll hear about how the Brewers own the division.
And we’ll have to smile, shrug, or pretend we don’t care.
But we do care.
That’s what makes being a sports fan so ridiculous and so wonderful. You invest your time, your money, your emotions, and your entire fall into a baseball team that has absolutely no idea who you are.
You let a game played by millionaires you’ve never met determine whether your Thursday night is enjoyable.
You allow a division rival’s success to ruin your mood.
And somehow, you keep coming back.
Because when the Cubs finally do get there again, when they finally give us another October worth remembering, none of this will matter quite as much. Every miserable season, every crushing loss, every time Milwaukee got the better of us will become part of the story.
That’s what we tell ourselves, anyway.
Right now, it doesn’t feel like a story building toward a happy ending. It feels like an endless cycle of hope, disappointment, and watching the Brewers do something else that makes us miserable.
So, What Now?
I don’t know.
That’s the honest answer.
I’m not ready to congratulate Milwaukee. I’m not ready to tip my cap and talk about how impressive their organization is. I’m not ready to sit back and enjoy the moment for what it is.
I’m a Cubs fan. They’re the Brewers. There’s a limit to how much graciousness I can muster here.
I’m angry that they’re going to the World Series. I’m angry that the division has felt like theirs for so long. I’m angry that we hired their manager thinking it might finally change things, and here we are, still watching Milwaukee celebrate.
Mostly, though, I’m disappointed.
Because three years ago, I genuinely thought we were turning a corner. I thought bringing Counsell to Chicago was going to mean something bigger than a managerial hire. I thought it was the beginning of a Cubs team that would finally make the Brewers look over their shoulders.
Instead, the Brewers are four wins from a World Series title, and Cubs fans are left looking at the same old problem: Milwaukee is winning, and we aren’t winning enough.
I want to be optimistic. I want to believe the Cubs are going to get their moment. I want to believe there’s a season coming when we won’t have to watch Milwaukee celebrate anything.
But today? Today, I’m tired.
I’m tired of the Brewers being good. I’m tired of watching them win. I’m tired of feeling like they’re always one step ahead. And I’m really tired of being told that the Cubs’ time is coming when the team standing in our way keeps proving that it knows exactly what it’s doing.
So go ahead, Milwaukee. Enjoy your moment.
I’ll be here, wearing my Cubs gear, rooting against you with every ounce of bitterness I can find.
And when it’s finally our turn, I promise I’ll remember every second of this.
Because if there’s one thing Cubs fans know how to do, it’s hold a grudge.
But seriously, Brewers? The World Series?
I hate this. I absolutely hate this.
And the most frustrating part of all is that I have absolutely no choice but to watch it happen.