McCuddy’s, then Comiskey, if at all

The Sox are in the playoffs. And winning? That’s not nothin’.

Chicago · 3 October 2026

My dad used to bring me to McCuddy’s with him before we went into Comiskey. Harry Caray was still calling @whitesox games then. The neighborhood was alive.

Camaraderie and being packed like sardines is what I remember about McCuddy’s. And loud. We missed a lot of games staying at the bar. Some of the best memories I have are in that neighborhood.

The neighborhood will be alive this week. The Sox are in the playoffs. And winning? That’s not nothin’.

My dad never hated on the @Cubs, or anyone for that matter, and I don’t do it today. It’s annoying. It’s barely tribal, and in 2026 it’s bullshit as far as I can tell. The ’70s and ’80s saw so many players move across town, Sox to Cubs and back. Even Harry went across town. So what. My dad taught me the business side, so it seemed weird to hate on anyone outside the owners.

I’m sober these days. Pete Hamill said it best when people asked him why he quit drinking. “I have no talent for it.” That won’t change what a winner feels like to the South Side.

This became a South Side piece by accident. I hope all of Chicago appreciates this time of year, if not the Sox.

These weeks in general are some of the best of the year. The air is lighter and crisper, the sun feels perfect, and it can be easy to miss if you’re in a hurry, preoccupied or on your phone. Like I am now, writing about it.

If you live on the North Side of Chicago and haven’t figured out how to get lost in the magic of the trees, the foliage, the pathways, the beaches and the parks, you’re not doing it right. And if you’re taking a Lime scooter when you could be walking across neighborhoods, you’re missing the plot too.

Nelson Algren wrote that loving Chicago is like loving a woman with a broken nose. You may find lovelier, he said.

“But never a lovely so real.”

Nelson Algren, Chicago: City on the Make, 1951

It sums up Chicago better than anything I’ve ever read. Honestly, it’s why I always came home. I never found the realness anywhere. New York had it if you were deep in the generations, I’m sure, as do others. Twenty years in SF, in Silicon Valley, and I feel lucky I never lost touch with that.

I’ve had a broken nose. My wife loves it. Says the bump added character.

Chicago has never been short on character.

See you out there. I won’t be on my phone.

Sources

The RulesThe RecordArchive