A Hyde Park man named Chester appears in one of Airbnb’s ads attacking the mayor. Credit: The Internet Association

At around the same time that Alderman Ameya Pawar was blasting Governor Bruce Rauner last week, former alderman Will Burns was lighting into Mayor Rahm Emanuel. Well, not Burns directly, but Airbnb—the company he works for.

The point is, you effectively had one old mayoral ally undercutting the efforts of a current ally, who was trying to make the mayor look good in his fight with Rauner.

If you’re confused, I don’t blame you. It’s always hard to keep up with the shifting alliances in this town.

A little background might help.

In my mind, Pawar and Burns will always be linked as the smart guys Rahm turned to in the first years of his reign, when he needed a surrogate to offer a little progressive spin on his policies.

As such, I had many conversations with Pawar and Burns that went a little like this:

Me: Why are you pimping for this schmuck?

Them: What you don’t understand is, if you want stuff for your ward, you got to play the game.

Pawar is still at it, more or less. On Thursday he released a statement in which he blasted Rauner as a “terrible person.”

This statement came a few days after the mayor ripped Rauner—his old business partner and wine-drinking pal—for vetoing his police- and fire-pension bill.

Pawar tells me there was nothing choreographed about his comments. It’s just a coincidence that he delivered them on the same day other Emanuel allies—Alderman Howard Brookins and CPS official Janice Jackson—were also ripping into the governor.

OK, Alderman. And sometimes a cigar really is just a cigar, as Mr. Freud once said.

Pawar says he was set off by Rauner’s comments—the governor blasted house and senate Democrats, accusing them of “competing” to see “who can spend more to bail out Chicago with . . . tax dollars from southern Illinois and central Illinois,” the parts of the state full of “hardworking families” who “pay their taxes,” according to the governor.

As if Chicagoans aren’t hardworking and don’t pay their taxes.

Yes, Alderman Pawar, I share your outrage—Rauner really is a royal ass. But it’s not as though Mayor Rahm had no hand in his creation. In some ways, Rahm is Dr. Frankenstein and Rauner is his monster. Back in the early days of the mayor’s tenure—when he was trying to position himself as the kind of Democrat that Republicans could work with—Rahm put Rauner’s wife on his transition team and named Rauner to World Business Chicago, an advisory group. That gave him the credibility to run as a bipartisan businessman who could save our state.

That was what Rauner promised, remember?

Noticeably absent from the Rauner-blasting chorus was Burns, who might have been leading it had he not stepped down in February. During his stint as Fourth Ward alderman, Burns was one of Emanuel’s closest allies. In the last mayoral race Burns oversaw Emanuel’s campaign in three south-side wards. And Emanuel rewarded Burns for his loyalty by putting him in charge of the City Council’s education committee, where he dutifully bottled up proposals that the mayor didn’t want adopted.

But things have changed since Burns stepped down as alderman to take a job as director of midwest policy for Airbnb.

If Chuy Garcia had been able to saturate the airwaves like Airbnb, he might be mayor today.

Soon thereafter, Airbnb began negotiations with the city over an ordinance that would regulate the home-sharing industry.

Residents in the Gold Coast and Lincoln Park—the mayor’s political base—called for restricting the number of units Airbnb can rent in the city. Naturally, Airbnb wasn’t a fan of that idea.

So the mayor had to choose between the company that employed Burns, his old ally, and the wards that gave him roughly 80 percent of their vote.

As Airbnb sees it, the mayor’s sided with the Gold Coast with his ordinance, which is set to come for a council vote later this month.

In response, the company counterattacked. In an attempt to rally a majority of aldermen against the mayor—good luck with that—the Internet Association, a trade group of companies including Amazon, Facebook, and Google, unleashed a series of radio spots and TV commercials blasting Mayor Rahm on behalf of Airbnb.

Let me tell you, as a guy who was bashing mayors long before it was fashionable, this is pretty good stuff.

The radio spot goes like this: “Do you think wealthy special interests downtown deserve another sweetheart deal from the city?”

Sounds like one of my privatization stories.

“They are pushing the mayor’s office to pass a special law at the expense of people in our neighborhoods.”

Or one of my TIF stories.

“Those downtown special interests want to make it really hard for people in our neighborhoods to rent out their homes for short periods of time.”

As though the only reason Airbnb’s in business is to look out for the little people.

“What we need is a revolution of the proletariat!”

Oops. That may have been an e-mail I recently got from one of my friends. My bad.

Here’s the real ending: “Tell your alderman and the mayor not to put the special interests downtown ahead of our neighborhoods.”

The company is also running two TV commercials, with more to follow.

My favorite stars a cool cat named Chester. He’s a jazz guitarist who also works as a substitute teacher and high school wrestling coach for CPS.

As Chester tells the story, the mayor’s ordinance would force him to give up renting his apartment, and thus cut him off from the cash he needs to stay in Chicago.

“If he’s the mayor, he should be the mayor of every street corner all over the city,” says Chester. “I would say to Mayor Emanuel, ‘Leave the little guy alone.'”

Great line. Wish I’d thought of it.

Burns has no comment on the ads other than to remind me that city law prohibits him from having anything to do with lobbying the council or the mayor for a year after leaving office.

The mayor’s spokesman has slammed the commercials as unfair and counterproductive.

Coming at a time when the mayor’s trying to depict himself as the friend of Chicago who’s standing up to Rauner, the commercials hit him where he’s most vulnerable—they make him look like a tool of rich guys who doesn’t give a shit about ordinary Chicagoans and remind people why he’s known as Mayor 1 Percent.

Hell, if Chuy Garcia had been able to saturate the airwaves with a similar message, he might be mayor today.

You know, it’d be interesting to see how Chuy would deal with Rauner’s lunacy. v

Correction: An earlier version of this story mistakenly stated that the mayor had appointed Rauner to his transition team. It was Diana Rauner, the governor’s wife, who had been appointed to the transition team.