This gay Cubs fan dishes on how it all fell apart in the playoffs against the Brewers

Welcome back to Talkin’ Gaysball where, alas, “Go Cubs Go” is once again our favorite funeral dirge…

It was the kind of move that a catty baseball gay dreams of.

In 2023, the Chicago Cubs lost the NL Central Division title to the hard-charging Milwaukee Brewers. It was the latest of several years being frustratingly outperformed by their small market neighbors to the north.

So in response, when Brewers skipper Craig Counsell’s contract expired that offseason, the Cubs came out of nowhere and signed him to a record-setting $40 million contract.

The move was “Mean Girls”-level petty and it was delicious. At Counsell’s introductory news conference, it was a genuine upset that the Cubs didn’t unveil pink alternate jerseys to wear on Wednesdays.

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Based on Cubs President Jed Hoyer’s “This is my Leadership Face” expression of self-satisfied smugness from that day, it was clear he felt he was the new I-94 Queen Bee. At long last, the gossip table at the Mars Cheese Castle would finally whisper his name in fear.

This was a story that so many high-drama gays could relate to. A conniving villain steals your man and you resign yourself to spending the next several years watching them live it up together from afar and cursing their names every time you open you open Instagram. After years of milquetoast mediocrity, the Cubs were finally entering their villain era!

Two seasons later, after the Cubs were eliminated by Milwaukee in the Division Series, it’s become abundantly clear that the Brewers had no problem at all moving on. And once again, it’s the Cubs going home to watch them living their best lives with their new man.

All because Hoyer neglected to follow up on his managerial heist by giving Counsell anything resembling a roster that could put the Cubs over the top.

Last year, the Cubs maddeningly sat on their hands for months after the Counsell press conference, signed Shota Imanaga in late winter, and called it an offseason. Then they were somehow surprised when Counsell finished with the same 83-win season that got his predecessor fired.

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This season, after landing game-changing All-Star Kyle Tucker, things looked different. The villain-era Cubs finally appeared ready to complete their climb to the top of the Central during an impressive first half of the season. 

But at the same time, everybody in baseball knew that they needed a starting pitcher at the trade deadline to add to their starting rotation, which had performed decently but was injured and operating at least one player short. 

Instead of bringing in an impact arm, Hoyer took no risks and tried to make journeyman Michael Soroka happen.

Soroka was the baseball equivalent of matching with a torso on Grindr, asking for a face pic, and receiving a photo of an eyebrow. Technically an answer to the question but NOT HELPING ANYONE.

Hoyer’s big acquisition promptly got hurt after two innings in Cubs pinstripes and was relegated to mop-up duty.

While the Cubs were dithering, the Brewers won 14 games in a row and left them in the dust for the division title. Again.

Then when the two teams met for a taut NLDS, the winner-take-all Game 5 essentially boiled down to the starting pitcher each team chose to handle bulk innings. 

The Brewers went with phenom Jacob Misiorowski who blows hitters away with 103 MPH fastballs and disgusting sliders. The Cubs had to go with Collin Rea, a fifth starter who … probably makes his mother very proud.

With that as the match-up, Milwaukee’s clinching win felt almost preordained.

For two years in a row, the overall result has been the same. Counsell and the Cubs have continued their residence in Brewers’ fans heads, reveling in the booing crowds at American Family Field. 

But at the same time, Milwaukee’s front office has continued lapping Hoyer on less-dramatic subjects like roster construction and player development. Now yet again, it’s the Cubs checking social media in October and seeing the Brewers mocking them during their playoff celebration.

Oh, and their new man Pat Murphy quotes Shakespeare. Poorly, yes! But he’s probably at least read the Cliff’s Notes.

Under Hoyer, the Cubs have been loath to make any move if negotiations go even a fraction beyond what he has calculated is optimal value. It happened yet again at the 2025 trade deadline and made the result of the NLDS a fait accompli.

So while the Cubs signaled that they were going Full Regina George when they pilfered Counsell from Milwaukee, the reality of the experience has been more like giving fans a two-second glimpse of “Mean Girls” while flipping channels to CNBC.

It turns out that they might need a better strategy than “Get in, loser, we’re going shopping. But not for anything that makes Tom Ricketts uncomfortable.”

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