Things were different here. Royko (RIP) said as much, back when this city was still Second City (now best known as some shit improv troupe; I’d rather visit Bedlam), something Chicagoans took pride in. Things change.

Now Royko’s column is occupied—like a meth-head squatter—by the biggest TruCon Boomer in the Northwest: John Kass. Fitting. We get the columnists we deserve. “We Don’t Want Nobody Nobody Sent” was the old motto. For the Trib (Tronc?), now it’s “you get what you pay for.” I met Kass’ son once at IU. Complete cunt. Couldn’t handle his liquor. Greeks…

Most of you probably haven’t heard of Kass. There is a God. But I digress.

Things change. Read your Parmenides: panta rhei. We have the gangs still, but the machine ain’t what it used to be. Instead of Boss Daley, it’s Ms. Preckwinkle—a bucktoothed marm turned pol—running the show. Alderman Burke used to be a gatekeeper. Now some chump like Gery Chico can run for mayor and renounce his endorsement (all over a silly little Fed indictment). That being said, Boss Madigan is still the King of Illinois (that’s not me, that’s Chicago Mag speaking, as well as every disgruntled Republican in a suburban dive), and Governor Pritzker (the world’s first billionaire-henchman) will play ball. But Chicago’s the fiefdom: something that needs to stay in machine hands.

But as I sit in this Mick bar, and I look at the bronze busts of JFK and Mayor Daley (Boss to you), I see a glimmer of hope. Not of any meaningful political change, of course. That’s not what this city’s about. I close my eyes and think of this beautiful city where all the mayoral front-runners are connected to a machine-pol with fed indictments. Yep, I’m thinking the boys are back in town.

Let’s look at the 2019 mayoral candidates, starting with the chumps and leading to the legit.

John Kozlar

A millennial nobody. King of the chumps. No endorsements. Less than two grand in the purse. I took a look at his campaign website, “Enough of the elitist and machine politicians running our city…it’s time to take Chicago back.” Need I say more?

Neal Sales-Griffin

He’s black, so he has that going for and against him. He’s also got $150,000 in the purse to buy a Trans Am when he loses, spinners and all! Also no endorsements. Apparently, the Sun-Times had a poll: he didn’t get a single vote. Hey, he might be top of the table in the Defender!

La Shawn Ford

90 grand down the drain. No endorsements, either. What does he think a candidate is supposed to do with $90,000? Also, Chicago will never have a mayor called “La Shawn.” We had a race row when we elected our first negro mayor. His name was Harold Washington. Pack it up, son.

Bob Fioretti

Bob’s been trying to get one over on the establishment ever since John Arena and Pat O’Connor double-teamed his wife and (worse) redistricted him out of his ward in 2015. $700,000 worth of cash would be better spent getting his wife into Kegels.

Jerry Joyce

A nobody who somehow got a shit-ton of treasure (his wife gave it to him). $2 million is nothing to sneeze at, especially if he promises $40,000 to each of his potential voters.

Garry McCarthy

A man reliant on white conservatives, so much so he proposed Chicago annex the inner suburbs. Unfortunately for McCarthy (and BAP), you can’t annex lands to make yourself king (yet).

Willie Wilson

I won’t lie: I’ve got a soft spot for Willie. He won’t win, but you gotta love him. Some excerpts, courtesy of the Mag:

MIKE FLANNERY: “Name your favorite book, other than the Bible.”
TONI PRECKWINKLE: “American Pharaoh.”
SUSANA MENDOZA: “Team of Rivals.”
GERY CHICO: “Master of the Senate.”
PAUL VALLAS: “The Guns of August.”
WILLIE WILSON: “My own, because it’s not corrupt.”

He also famously said, “If I closed 50 schools in the white community, you’d hang me at State and Madison.” Slick Willie is where we move from chump to plain-old “won’t win” territory. God bless him.

Amara Enyia

Presented without comment.

Paul Vallas

A career bureaucrat who thinks he can kill a Daley. A damned fool. Lacks the money, lacks the charisma. (Sorry @2cb, but I know you know better.)

Lori Lightfoot

She’s recently gotten some praise as a trailblazing queer politician, and she’s not connected to the Burke-Madigan machine (she’s endorsed by the Sun-Times, even). She’s hip, she’s exciting, she not bought and paid for! She will lose, of course.

Our next installment will cover the Burke Four, the four pols who are too close to Alderman Ed Burke, who’s facing some serious charges. They are, of course, the frontrunners: Mendoza, Chico, Preckwinkle, and Big Bill Daley. They also all have the biggest war chests: a little under $20 million when you add it all up. Welcome to Chicago.

It’s when I consider all this that I realize a pol’s necessary art is grift. What was amateur shit for the Tammany micks became an art in Chicago. Perhaps I could learn this art from Alderman Miyagi. Wining and dining is key to this. Here’s my advice: learn wine, and learn grift. I can picture it now:

I grow rich through a combination of classic Chicago political grifting and serendipitous profits from investments I would be wise not to discuss with strangers. Retiring from “fighting for the working man,” I buy a Napa vineyard and live a life of Bacchanalian decadence. I’ll buy a Porsche, even! Sitting at the head of a long dinner table in my wine estate manor, I’ll regale my Croatian wife and ten children on the finer points of the geomorphology of our terroir. They will beg me, “Papa, please, no more!” but their cries for mercy will go unanswered. “You know, I am told our Cru is reminiscent of Château Margaux’s!” My wife will wonder if I have discovered her affair with the assistant estate manager, and if this is the punishment I have decided upon. Oenological tidbits will shoot from my mouth like artillery salvos, and like Napoleon at Austerlitz, my enemies will have no recourse. Take no prisoners: that’s the Chicago way.

Until then, it’s Old Style.


For all installments of “Transmissions from Chicago,” click here.