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The well-rewarded bootlicker has always been the mainstream character of New York, exemplified in many, including New York hero Alexander Hamilton, so lauded that he has a play named for him and his bootlicking existence. I will take a gutsy John Kass any day.

The Best Political Writer You Never Heard of

By Allan Stevo

One day, Mike Royko was all done. Mike Royko was on the second page of The Chicago Tribune. Boy did he write some good politics. He cut down the Daleys in his writing like nobody’s business.

He played softball — 16 inch, like a true Chicagoan. 16 inch is the kind of softball you can play with no mitt on one hand and a can of  Old Style beer in the other hand. The ball is soft. The home runs are fun. The thing just lobs off the bat through the air.

He was culturally of Chicago — a Polish mom and Ukrainian dad. Though he was a journalist, he was very much a working class man. And through a combination of playful characters, telling snapshots of life, and observations on Chicago corruption he wove together a world that his readers could enjoy.

There was a Saturday Night Live skit in the 1980s about a place they called the Olympia Cafe on the show. “Cheezborger. Cheezborger. Cheezborger! No fries, Cheeps! No Pepsi, Coke!”

Look it up and watch it if you don’t know what I’m talking about.

This skit was about the real life Billy Goat Tavern. It was (and still is) located on Lower Michigan Avenue, an underground street in Chicago, that I can’t imagine anyone wanting to open a business on. You had to step past bums in cardboard boxes to get there. It was steps away from the two headquarters of the two rival newspapers in town, so the Billy Goat was where the rough-around-the-edges Chicago journalists would often hang out.

Saturday Night Live has a history of being a New York City show that relied on edgy Chicago talent. Wealthy Manhattanites have a long history of slumming it in Chicago when they want a truthful slice of life. They just couldn’t get that the same way from their fellow New York bootlickers, which gets to the heart of why Saturday Night Live has become unwatchable — no guts, all bootlicking.

Before Saturday Night Live’s writers got wind of the Billy Goat and made it famous, it was Mike Royko who wrote about it and made it the thing of legends: that place, its owner Bill Sianis, “the curse of the Billy Goat” (which gave the Chicago Cubs one nightmare of a losing streak), and a lot more.

Royko knew how to write politics, but he also knew how to grab you by the heart.

Royko wrote a brutal book, called The Boss. It introduced me to a side of Chicago I never knew I was part of, but I always had a feeling I was a part of. “The best book ever written about an American city by the best journalist of his time,” said Jimmy Breslin, a New York columnist. In it Royko describes Chicago’s culture of corruption and absolutely ridicules the corrupt mayor and his henchman.

The unapologetic ridicule is the best part.

Though few today have heard of it, the book is so powerfully effective, that just this past Saturday, during a class I was teaching to about fifty conservative activists in California, a woman brought up the book to me during the question and answer session. She said it taught her so much.

Ridicule, truth, guts, and good writing is a hard combination to beat.

Royko left his job in 1984 when Rupert Murdoch bought the paper. Tokyo commented at the time “No self-respecting fish would want to be wrapped in a Murdoch paper”, and said about Murdoch, “His goal is not quality journalism. His goal is vast power for Rupert Murdoch, political power.” Royko switched to a rival newspaper to continue his writing — The Chicago Tribune. 

Boy was he a writer and one who so exposed the corruption of Chicago, shining an uncomfortable light in the dark places. But he wasn’t my guy. My guy is named John Kass. That is the best journalist you’ve never heard of.

John Kass was awarded the coveted place Royko once held, on the second page of the The Chicago Tribune, the top third of the page. For many Chicagoans, that was Royko’s place and for me that was John Kass’s place. He wrote powerful, revealing articles about Chicago culture and Chicago politics, and he did so with intelligence, bluster, humor, and working class sensibility.

And to this day, I’m not sure why someone has not yet killed the guy for some of the things he wrote — such as observations he would write while attending mob funerals. Bad enough he was even at the mob funeral taking notes in his little journalist notepad during such a private moment, observing who came to pay their respects — but he went further. He would write about it in the newspaper.

The man understood the weapon he had and used it. He continues to do so.

Far from being a Mike Royko understudy who lives in the shadow of a great man, Kass is in a category all his own. Kass is not just a political columnist, but a brilliant, hardly-known, literary figure, in an era that would never call him such a thing as literary, but that he is.

Politically, he is too far on the fringes for him to win literary accolades, but on the fringes is where the best thought and experimentation can take place. The lack of relationship with the fringes of acceptable thought is, again, exactly why Saturday Night Live has grown stale.

John Kass wrote an article one day in the late 1990s, or early 2000s, that set him in stone as my favorite newspaper writer for life. Because the era of the print journalist is behind us, I suspect he will forever hold that spot.

That article he wrote was in the style of Ring Lardner, a classic columnist of the past, a style probably not 1-in-10,000 readers of his column could appreciate, and boy did he get it spot-on. It was like an Easter egg. He didn’t overtly state that he was writing in the style of Ring Lardner, but to anyone who knew Ring Lardner, it was evident and so well done — a wonderful little surprise for the right readers. This was in the days before comments under online articles were the norm. It was in the days before internet searches were the norm. A journalist takes a lot less risk today writing such an article, because someone in the comments will inevitably explain what the writer was doing.

It wasn’t like that then.

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