One of John Kass’s motifs is that other journalists are suck-ups and mythmakers (not all of them, but enough), so I think it’s a safe assumption that they don’t like him either. My column this week praises Kass, and when it appeared online I promptly heard from a reporter in town who called him a phony and told me to look at this video.

I did. The video—made by the Tribune, which I have to suppose is proud of it—finds Kass and Mayor Rahm Emanuel exchanging presents in the mayor’s office a couple of days before Christmas 2012. Both are in high spirits.

We see Emanuel give Kass a bicycle owner’s manual and—”because I know you never get on a bike”—training wheels. Kass and Emanuel high-five each other. Then Emanuel unpacks Kass’s gift, which is a large framed poster of the mayor as “The Rahmfather”—a poster he’d written about before and said Emanuel could never have. “Oh my God!” says the mayor as he pops the box open. They crouch beside the poster for pictures, crack a couple more jokes, shake hands, and the video ends.

So what of it? Kass isn’t deferential. They meet as a couple of high-order personages who each knows the value to himself of a cordial relationship with the other. If they also meet frequently for lunch, which I’m told they do, good for them. Kass’s journalism won’t suffer for actually knowing what’s on the mayor’s mind.

The problem is that Kass doesn’t position himself in his column as a mover and shaker in an expensive suit with easy entree to the Fifth Floor. He scolds those guys for operating as a cabal that crosses enemy lines. “What do we call this relationship, again?” he wrote in 2008. “This Illinois custom of quiet sharing of power across party lines for the benefit of a fat connected few?” He went on to say that former U.S. senator Peter Fitzgerald (a Kass favorite) provided him with the answer.

“The Illinois Combine,” Fitzgerald said. “The bipartisan Illinois political combine.”

Kass continued, “I’ve been calling it The Combine for about a decade but hardly see it referenced elsewhere, and I don’t want others to think I’m hoarding the Illinois Combine all to myself. Today, I’m sharing. I’m inviting other colleagues—political writers, editors, broadcasters and any combine suck up professors — to use ‘Illinois Combine’ particularly if they’re having difficulty explaining how two parties can be as one when there’s money on the table.”

Did Kass cross enemy lines when he showed up in Rahm’s office bearing gifts? Some readers who believed Kass stood with them as a matter of class as well as philosophy might have thought so. Kass is pretty scornful of journalists who don’t draw a line. Here he is a couple of years ago on the Washington media.

There’s no better place to witness journalists wiggly with celebrating the status quo than at two amazing gatherings: the White House Correspondents’ Association dinner and, even worse, the Gridiron Club dinner, in which reporters perform musical numbers for the Washington political establishment.

The correspondents’ dinner is about guest status. The media outlet whose table includes a new chief justice or the eye candy on the arm of George Clooney is considered a smashing success.

The Gridiron is about singing and dancing on stage, and the president applauds as the journalists put on a musical show. They wear costumes, and the lyrics of their songs are replete with witty inside jokes.

What these rituals accomplish is to wed journalists to the establishment.

In addition to the Illinois combine and journalists with their noses deep in the establishment butt crack, Kass likes to assail the “Chicago way.” “Once there were old bosses. Now there are new bosses,” Kass wrote ten months ago, in a piece I approvingly quote from in my column this week. “And shopkeepers still keep their mouths shut. Tavern owners still keep their mouths shut. Even billionaires keep their mouths shut.”

Let’s take a longer look at that piece. Kass was reminiscing about the conversations around the table when he was a kid and his extended family sat down for Sunday dinner in Chicago. “They were immigrants who came here from Greece with nothing in their pockets but a determination to work, and the belief that here, in America, no other power could roll in with tanks and put their boots on the necks of their children,” Kass wrote. “There were conservatives and socialists, Roosevelt Democrats and Reagan Republicans and a few bewildered, equivocal moderates in between, everyone squabbling, laughing, telling stories.”

But one day when Kass was 12 or 13, he asked a question that shut everyone up. “We talk politics every Sunday, we fight about this and that, so why aren’t you politically active outside? Why don’t you get involved in politics?”

“The aunts and uncles stared at me in horror, as if I’d just announced I was selling heroin after school. You could hear them breathing. No one spoke. I could feel myself blushing.”

Finally his father responded. “Are you in your good senses?” he said. “We have lives here. We have businesses. If we get involved in politics, they will ruin us.” And no one disagreed. For this, Kass would come to understand, “was Chicago. And for a business owner to get involved meant one thing: It would cost you money and somebody from government could destroy you.”

Today Kass writes as that son of Greek immigrants who has grown older, wiser, and angrier, not as a mover and shaker in an expensive suit.

I don’t know Emanuel nearly as well as Kass does, but we have mutual friends, and more than once we’ve shown up at the same parties. Also at those parties, come to think of it, was one of the most prominent muckrakers in Chicago, having as good a time as anyone else. What everyone had in common was that we owned weekend places out in the dunes. Kass is right about the status quo: reporters aren’t as eager to challenge it once their own start looking pretty good. Or maybe the thing to remember about most journalists is that, like Kass’s father and uncles, they don’t actually get involved in politics either. They talk about it endlessly, and they talk publicly, but most of them don’t really do anything. If they confuse their punditry with action, smart politicians are too polite to correct them.

Of course, Kass didn’t call on the mayor at City Hall bearing gifts strictly on his own behalf. The Tribune Company thinks of itself as one of the most powerful and enduring forces in the Chicago establishment, and that was the Tribune a step behind with its video camera to record the meeting of titans. The Tribune was doing Kass no favor.

But there he is in the video—dapper, glib, and at ease—and what’s a faithful reader to think? The faithful reader should remind himself of this: Kass would be far from the first newspaper columnist to kick back and unstrap his public personality.