Letter From Milo: Secret History of The Third City, Part 91

January 26th, 2015

When Benny Jay had the brilliant idea to start a blog site, his intention was to provide a showcase for the best writers in Chicago. Unfortunately, no writer in town wanted anything to do with The Third City. Most, in fact, wouldn’t even return Benny’s phone calls. The few that responded to his calls just told him to fuck off.

Out of desperation, Benny called me. “Hey, Milo, how would you like to write for The Third City?”

“Fuck off.”

“Come on, man. This is important to me, and you owe me a few favors.”

”What’s the pay?”

“Heh, heh, we can discuss that later.”

“Okay, I’ll do it.”

“Great! Now, what are your areas of expertise?”

“I don’t have any.”

“You must be good at something. Everybody’s good at something.”

“Well, I’m pretty good at drinking, smoking and whoring. I can shoot a decent game of pool and I know a few card tricks.”

“Excellent! You’re now officially the Society, Lifestyle and Religion columnist for TTC. When will your first column be ready?”

“I don’t know, maybe in a couple of months.”

“I need it by Monday.”

“Ah, shit!”

In time, talented writers and artists began finding their way to The Third City. John Randolph gave up a lucrative career in boudoir photography to become our staff photographer. Rolando quit his day job as a para-gynecologist to become our Medical Affairs correspondent. No Blaise renounced her vows and left the convent to join our staff.

Jim Siergey, wearing only a bathrobe and slippers, wandered away from the Retired Cartoonists’ Home, in Mokena, and showed up, three days later, at our plush Michigan Avenue offices. He was immediately assigned to the Old Curmudgeon’s Desk.

Despite my misgivings about the blogging business, I discovered I had a real gift for it. In a short time, my blogs became wildly popular. The Third City’s readers came to rely on me for sound advice, brilliant insights, and spiritual enlightenment. I was doing so well that in less than a year I was promoted to the exalted position of partner.

But best of all, the money was rolling in, an obscene amount of money, more than I had ever earned honestly. I was rolling in the dough. I felt like I had won the lottery.

It was a life-changing experience. I quit shopping for clothes at Sears and started wearing bespoke suits made by the same tailors who dressed Sidney Korshak and Irv Kupcinet. I quit hanging out in dive bars and began frequenting the finest watering holes in Rush Street’s Viagra Triangle. I was able to lose a lot more money at the track than I could when I was a poor boy. I could order oysters and steak sandwiches any time I wanted. I bought a Cadillac. I acquired a long-legged, busty mistress and set her up in a Gold Coast apartment. I invested in several fried chicken franchises. I got season tickets for…


This is Mrs. Milo. I saw what my husband was writing and chased him away from the computer with the can of pepper spray I keep handy for occasions like this. I can’t believe the crap he writes for that stupid blog. The Third City doesn’t have an office on Michigan Avenue or any other place. If those other losers who write for the blog are anything like Milo, they spend all of their time in dingy basements, dressed in a ratty bathrobes, drinking Old Crow, and sitting in front of cheap computers. In fact, the only time Milo leaves the house is when he sneaks out to the garage to smoke pot. There is no Cadillac. There are no season tickets. As for the mistress, if any woman out there wants him, they can have him and good riddance.

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Benny Jay: A Fiduciary Tribute to Mr. Cub

January 25th, 2015

In honor of Ernie Banks–who died just the other day–we bring to you the following memory, most of which is probably true…

It’s a soft summer night in 1983 or maybe `84…

We’re sitting on the front stoop of Milo’s two-flat apartment in Lakeview–just a few blocks from Wrigley Field.

It’s me and Milo on the front step. And Roger–Milo’s old friend from Gary, Indiana–behind us.

As I recall, we were smoking a joint. Or Milo was smoking a joint. By this time I believe I’d stopped smoking joints.

It doesn’t matter.

What matters is that Milo was railing against the Tribune company–which then owned the Cubs–for having unceremoniously dumped Ernie Banks from his position with the team.


Mr. Cub!


Apparently, Ernie had a deal with the previous Cubs owners that obliged him to do little more than hang around the ballpark shaking hands with fans.

As Milo saw it, Ernie had earned that easy gig on account of the fact that he was the greatest Cub–ever!

Our conversation went a little like this…

“Those lousy motherfuckers!” said Milo.

“I hear you,” I said.

“How can you fire Mr. Cub?”


“Those dirty sons of bitches!”

“I’m with you 100 percent!”


Milo & Roger back in the day…


“You don’t see the Yankees firing Mickey Mantle, do you?”

“No way…”

“Right now the Yanks are paying Mickey Mantle $100,000 just to walk around the ballpark being Mickey Mantle.”

“You’re right…”

“Joe DiMaggio, too!”

“Yeah, man…”

“That’s it–from here on out, I’m through with those fucking Cubs!”

It was at this point that, from the back of the porch, came the voice of Roger, speaking his first words since Milo went on his tirade. Until then, we’d forgotten he was even there.

“Well, the Tribune does have a fiduciary responsibility to its stockholders,” he said.

Folks, let me tell you–Milo and I were stunned into silence.

This may have been the first time we’d ever heard the word fiduciary. I’m not sure either one of us even knew what it meant. But it sounded really impressive coming from Roger.

In my opinion, with that one comment, Roger established himself as the smartest kid to ever graduate from the public school system of  Gary, Indiana. Well, right up there with Milo, of course.

In any event, there and then Milo put some kind of ancient Serbian curse on the Cubs, which has kept them out of the World Series ever since.

Of course, they hadn’t been in the World Series in almost 40 years before that night on the porch. So maybe there’s more to their failure than Milo’s curse.

R.I.P, Mr. Cub!

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Rolando: Dispatch From Mexico

January 24th, 2015

When Benny Jay and Milo called me to tell me the news that they were sending me and one guest down to Mexico on the company’s dime for a job well done, well, let’s just say I was a little skeptical.

I was at home, clacking away at my keyboard, hard at work, when Benny Jay and Milo called.

“Hey, Fuck Face, it’s Benny. I got Milo on the line, too. Whatcha doing?”

“Hey, Benny, just hard at work banging out this week’s copy,” I said. “What’s up?”

“Nothing. Me and Milo been talking and we decided it’d be good if you got out of the country for a little while.”

“What? Why? Has Milo been using my name to place his bets at the bookies again…”

“Hey, asshole, that was once and you only had to spend a couple weeks in the wonderful and always pleasant, Gary, IN until I sorted things out for you,” Milo interrupted.

“Oh, yeah. I remember. Thanks for that, Milo.”

“No, no, nothing like that you ungrateful bastard,” Benny Jay said. “We’re talking about sending down to Mexico for a few days cause you been doing some solid work for us.”

“Are you serious? You’re not fucking with me, are you?”

“Nope. And bring that nice girlfriend of yours,” Milo added.

“Yeah,” Benny Jay said. “You know, the one that is way too good looking for you and obviously out of your league…”

“Ok, Benny. I know who you’re talking about. And I happen to think we’re evenly matched.”

“Whatever you say kid, you’re both going to Mexico,” Benny said. “The company car will be by to pick you up this Thursday to take you to the airport. We’ll call you with details about your return trip in a couple of days’”

“Well, shit, guys. Thanks.”

I called my girlfriend to tell her the news and she, like me, met it with skepticism. But, hell, a free trip to Mexico? Who’s going to turn that down?

The next thing we know we’re on a plane and then we’re in Mexico.

I’m talking sunny skies with warm weather and beautiful beaches.

And everything is great, only our trip is nearly over now and we haven’t heard from Benny or Milo. I’m not too worried about it. I know how the guys can be sometimes.

My girlfriend isn’t haven’t it, though. She’s knows how the guys can be, too.

“What’s going on with those motherfuckers?” She’s asks me one morning as we lounged on the beach. “Not that I’m complaining about my current situation, but this feels a lot like the time Milo used your name to place bets at the bookies and we had to stay in that shithole Gary for two weeks.”

“I don’t know if you looked around, babe, but this isn’t Gary.”

Secretly I had a feeling she was right but I didn’t want to admit it until I got word from Milo or Benny. Two days later Milo finally called: “Hey, bud, how ya doing down in sunny Mexico?”

I already knew where it was headed…

“So why don’t you and that lovely lady stay down there a couple more weeks…”

Damn it, Milo.

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Randolph Street: Argentine Abstract

January 23rd, 2015


Osvaldo–Buenos Aires









Ezeiza Airport



Memory Park–For the victims of the ‘dirty war’–1976-1983


All photos © Jon Randolph


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Benny Jay: George Pelecanos

January 22nd, 2015

This all started about seven years ago, when, by chance, I read a Janet Maslin review of The Turnaround, a novel by George Pelecanos.

I’d never heard of Pelecanos. But according to Maslin, The Turnaround was “a hard-hitting urban parable” about six teenage boys who get caught up in “an ugly race baiting incident from 1972.”

That sounded like something I had to read, so I bought the book and it was, like–holy shit, where have you been Pelecanos! I mean, it was like he wrote this book just for me.

It was page after page of nailbiting action with realistic dialogue and gritty Washington, D.C. settings. Also, pithy asides and observations about blacks and whites and movies and cars and music, especially music. Also, sex. Hey, man, I like a good sex scene as much as anyone else.

After that, I was hooked on Pelecanos. I read the books he’d already written–King Suckerman, Right as Rain, Hard Revolution, etc. Then I started reading the new ones he was churning out like What It Was and The Cut and The Way Home.

I think Hard Revolution–set during the riots of `68–is my all-time favorite. Though, now that I think about it, King Suckerman‘s pretty freaking good.

Anyway, one day not long ago I was chatting with Josh, my old high school pal who now lives in Washington, D.C.

And he asked if I could recommend a book for Ben, his teenage son.


George meets Ben…


“What’s he into?” I asked.

“Rap. Skateboarding. Washington, D.C…”

“You might want to try the novels of George Pelecanos.”


So I launched into my refrain about how a book by Pelecanos has it all–Washington, race, music, action, sex. You name it!

To Josh’s everlasting credit, he went out and bought several Pelecanos novels for his son.

And now, guess what? Josh and Ben are hooked on Pelecanos. They’ve read a bunch of his books. If this keeps up, Pelecanos’s gonna have to cut me in on some of the royalties.

Anyway, that’s where the story stood until a few days ago when I got a packet in the mail from Josh. In it was a copy of Martini Shot, Pelecanos’ latest book.

Turns out that Josh and Ben attended a reading Pelecanos gave at a local book store in D.C.

And, dig this, they got him to inscribe the book they bought for me.

“To Benny Jay–I love The Third City. George Pelecanos.”

Okay, he didn’t really mention TTC. Maybe next time.

Thank you, Josh. That’s one of the nicest things one old friend can do for another.

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No Blaise: Knitting

January 21st, 2015

Every so often my stress about my life and where it’s going will get so high that I’ll decide to pick up a new hobby. These have been knitting, juice cleanses, reading the Harry Potter series from start to finish, dating, making my own almond milk, growing my nails out, a new iphone game, and now it’s back to knitting.

My refreshed love for knitting comes at a time when I am both really stressed out and really looking for a way to procrastinate that doesn’t include being on instagram for five hours and then realizing when I’m a photo of Kylie Jenner’s page that’s 40 weeks old that I need to get off my phone and stop frying my brain. Instead of transferring my brain power to the school work I could be doing while the boys I nanny nap, I decide on one of the above hobbies. And sometimes this “hobby” means digging around the house for food I would like.

Now that knitting is my hobby I’m sure you all are hoping it sticks so that you can have an original No Blaise Scarf or pot holder. Maybe someday you’ll get a hat. According to the knitting blogs knitting just about anything is “much easier than it looks” which means that they know how to do it and so they took pictures of themselves doing it and hopefully you figure it out. After watching three youtube videos, I can finally say I know how to do a basic stitch. I am going to be satisfied with this learning for the next year.

Again, this learning power could have been utilized for grad school, but a girls gotta have interests.

The first item on my list of “to make” is a dog scarf for Belle. I chose this because I want to eventually make a real scarf for someone, mainly myself, and making a smaller version for my dog somehow works for me. I’m also a crazy dog lady, which may have influenced the decision.

I started my new hobby yesterday and it took me pretty much all day how to figure out the basics. By the time I got home from work, the boys had napped long enough that I’d been able to make slight progress on the dog scarf. Unfortunately, I messed something up that I couldn’t redo so I had to scrap my first dog scarf. Luckily, it came out at just the right size for a dog bonnet. And what dog doesn’t need a dog bonnet this time of year? Since I have the perfect dog model, I took a picture of her modeling the first item in my dog clothes line, “Classy Bitch”. Get your first look below:



Classy Bitch; SS15

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