Benny Jay: Courthouse Contraband
I’m walking through the metal detector in the lobby at the criminal courthouse when the alarm goes off.
The alarm always goes off. I’m starting to think the doctors embedded a piece of metal in my leg when I was born.
The guard pulls me to the side. I’ll call him Larry. He looks like a Larry. Big old white guy with a doughy face.
“Empty your pockets,” he says.
I pull a few coins from my pockets.
“That must have been it,” I say.
I smile. He doesn’t smile back.
“Go through it again,” he snaps.
But….
Alarm goes off.
Larry pulls me to the side. “Raise your arms,” he says.
I raise my arms and he frisks me.
In my back pocket, he finds a few more coins and an unmarked plastic pill bottle with a couple of brown tablets.
He holds up the pill bottle and asks: “What’s this?”
“Ibuprofene….”
“What?”
“Ibuprofene.”
The guard looked a little like Brendan Gleeson from The Guard….
I start to spell it. Like that’s going to ease his suspicion.
“I-b….”
Then I realize — I’m lost once I get past those first two letters.
“It’s either I-b-e or I-b-u….”
He cuts me off. “What’s it for?”
“Headaches.”
“You have headaches?”
“Well, it’s not a chronic thing. Just in case I get a headache.”
He’s cradling the bottle in his hand, like it’s contraband I’m sneaking into the courthouse.
“Why isn’t it in a regular bottle?” he asks.
“I keep the regular bottle at home and what I do is — I take a couple of pills and put it in this other bottle that I’ve kept from another prescription and then I carry it around with me in case I get a headache.”
Just imagine what would have happened if I looked like Omar….
He’s look at me with such disbelief that even I’m starting to doubt the story. And it’s a true story — I swear, it’s true!
His questions come fast and furious…
“Why are you here?”
“I’m a reporter — covering a case.”
“Where’s your press pass?”
“I don’t have one.”
“Why?”
“Ugh….”
How do I explain this? I start babbling.
It’s such an invconvenience. You gotta go downtown. You gotta take a picture. And who has the time?
He cuts me off. “You can’t bring these pills into the courtroom.”
“Okay….”
“You’ll have to leave them in the security room.”
“Fine….”
Then he explains it’ll cost me ten dollars to retrieve the pill bottle.
“Ten dollars for two Ibuprofen pills?”
“Yes….”
“It’s not worth it. I could buy, like, two bottles of Ibuprofen for ten dollars. Just throw it out. Or you keep it. In case you get a headache.”
And then — it’s like he sees me for the first time. I mean, actually sees me as a person, instead of some faceless guy who set off the alarm.
As I like to say — when I look in the mirror, I see a young Paul Newman. But obviously, he sees some old, harmless dufus.
He waves his hand. “Just go.”
Even let’s me keep the pills. Well, why not? Anyone can see — it’s just Ibuprofene.
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Letter From Milo: That’s My Road Game, Jack
Benny Jay, my esteemed colleague here at The Third City, has a tough day job. He is a journalist, and his beat is City Hall. In the course of his work day, Benny routinely deals with some of the sleaziest, most conniving and treacherous bastards on the planet — Chicago politicians.
Anyone that knows Benny or has seen his work will agree that he is a fearless reporter, steely-eyed, dedicated, daring and relentless. He will go to any lengths to get a story. If there is breaking news in Hell, Benny will grab his laptop, clamp a knife between his teeth, and parachute into the Inferno, just to bring us the sordid details.
Yes, Benny is as tough as they come, hardened by journalism’s school of hard knocks. He’s seen it all and lived to tell about it. Still, a lifetime spent in the company of swinish aldermen, greasy ward healers, and pinky-ringed fixers can take a terrible toll on a man.
Surviving the rigors of political journalism in Chicago is not easy. After a long day of swimming in the cesspool of City Hall politics, a reporter needs to unwind. Benny Jay is no exception.
So, what does Benny do to relax after a long day at the office? Does he drink himself senseless, like any normal guy would do? Does he spend quality time with a skilled and motivated mistress? Or does he take my good advice and spend a few pleasant hours at Mr. Choi’s Opium Den on Argyle Street?
No, he doesn’t do any of those things. What the fucker likes to do is go bowling.
Benny Jay in his younger years….
That’s right, the great Benny Jay is a kegler. He’s got his own bowling ball and bowling shoes. And he’s been involved in a bowling league for years. Every Monday evening he goes to Timber Lanes on Irving Park Road and joins his buddies, Cap, Norm, the Young One, J Dub and others for a night of riotous, unrestrained bowling revelry.
Now, I’ve got nothing against bowling. I think it’s an excellent pastime for fat, beer-guzzling, bratwurst lovers from Milwaukee. But for someone of Benny Jay’s stature and experience, someone who has stared greed, hypocrisy and corruption in the face more times than he can remember, bowling seems like a rather tame undertaking. A guy like Benny should be climbing mountains, wrestling alligators, or playing high stakes baccarat in Monaco, not fretting over a 7-10 split.
My dismissive attitude about bowling resulted in an awkward moment a few days ago. Benny and I had just finalized a brilliant new scheme for screwing The Third City’s readers out of a great deal of money when he asked if I had any plans for the weekend.
The Third City’s editorial staff has a meeting….
“Yeah, I’m going to Steve Ivcich’s birthday party.”
“Where’s it at?”
“Some kind of club.”
“What kind of club?”
“It’s, ah, a bowling alley.”
“Are you shitting me! You’re going to a bowling alley. Are you going to bowl? Do you even know how to bowl?”
Normally, when someone asks me if I know anything about a subject, my instinct is to claim to be an expert. That’s because I’m a bit of a windbag, by nature, and have a hard time admitting ignorance of any topic under discussion. If I ran into NASA scientist and was asked if I knew anything about astrophysics, I probably say something like:
“Astrophysics is my road game, Jack. I paid my way through the seminary with the money I made on astrophysics. The only reason I’m not in the astrophysics business now is that I’d have to take a cut in pay.”
So, when Benny asked me if I knew how to bowl, I said, “I can’t believe you’re asking me that question. Bowling is my road game, Jack. I paid my way through barber college with the money I made from bowling. If I hadn’t gotten into the blogging business, I’d be on the PBA tour right now.”
Benny called me a couple of days later on the pretense of talking about the blogging business, but he really wanted to know about the party at the bowling alley.
“How was it?” he asked.
“It was fun. I had a good time.”
“Did you bowl?”
“Yeah.”
“How’d you do?”
“Pretty good. I bowled about 212.”
“Jesus, that’s pretty damn good. In fact, that’s real impressive for someone that doesn’t bowl.”
“Unfortunately, it took me three games to rack up that impressive score.”
“Are you saying it took you three games to knock down 212 pins?”
“Yes.”
Benny started laughing. “Maybe you better give up bowling and take up ping pong.”
“Ping pong! Did you say I should start playing ping pong? For your information, I’m a killer ping pong player. I’ve made shitloads of money playing ping pong. That’s my road game, Jack.”
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No Blaise: Insta-Addiction
I’ve written before about my addiction to Apple (the technology giant, not the fruit. Though I do also enjoy a good fuji)
I am still very dedicated to my phone, I’ve even written a blog on it before due to my apartments lack of Internet. Now, even worse than my addiction to my phone, is my addiction to the app Instagram.
For those of you that dont know, Instagram is basically a large picture sharing venue. Similar to Facebook in that you can comment and “like” the pictures people post. But way better than Facebook because it’s all pictures, which as it turns out, makes all the posts about 100,000 times more interesting.
That really cool skyline someone was describing on Facebook? They could post an actual photo of it on Instagram.
Your adorable niece? Post a photo of her on Instagram, the crowd will love it.
Get a pair of really awesome shoes? Post them on Instagram, make everyone jealous.
Wearing a really cute new outfit on a Saturday night around town, and you’re not sure you’re gonna run into everyone you want to while wearing it? Drunkenly post a mirror pic of yourself on Instagram.
Simple as that.
If you’re saying to yourself, “Why not just upload those photos to Facebook?” Well, it’s because there’s such a stigma attached to uploading on Facebook. People don’t want to go to your Facebook and hit with three photos uploaded daily.
If you upload a picture of your dog laying on it’s back and looking adorable on Facebook, people will be like “Ugh, nobody cares about what your dog looks like.” But on Instagram, everybody cares! The Instagram community will want that dog as their own so THEY can upload cute photos of it.
Side note–anyone who is disinterested in photos of cute dogs, on Facebook or otherwise, should be immediately defriended.
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Rolando: My Big Raise
Things have been moving along for me here at thethirdcity.org. It’s been almost two years since I submitted my first post, and since then, I’ve been contributing fairly regularly to the site. So much so, that I recently received my second promotion (I was demoted several months back, so technically it’s only one promotion.)
After some careful thought, Benny Jay was offering me my old regular staff writer job back.
I was more than happy to accept his offer. I mean, hell, being a staff writer for thethirdcity.org is great gig. There’s the wild parties Milo always throws at our plush Michigan Avenue offices, the company paid trips to Vegas and lets not even get started on what it can do for your sex life.

Our trips to Vegas usually look something like this….
So if Benny Jay’s offering you a gig, you accept.
He broke the news to me during a meeting we were having at his multimillion dollar north side mansion.
“So, you’ve been doing good,” he said, as he slowly rocked back and forth in chair in his living room, his feet up on a leg rest. “I mean, you’re writing good stuff.”
“Thanks, Benny,” I said.
“I’m serious. Funny shit. Milo thinks its great.”
“Well I’m trying, man.”
He paused for moment. He looked me in my eyes, squinted, and made the offer.
“So, you want your old job back? We can give you Saturdays.”
“Do I want my old job back? Fuck yeah I want my old job back, Benny.”
And with a handshake it was settled. I thanked him again and started to make my way out his living room when it hit me. He didn’t discuss a raise with this promotion.
I decided to bring it up. I stopped and turned to him.
“Hey, Benny, we didn’t talk about money.”
“What about it?” he said with out looking up at me.
“What do you mean ‘What about it?’ I’m talking about, you know, maybe a little something extra then what you’ve been giving me.”
“Are you out of your fucking mind? We pay you a six-figure salary and you want ‘something extra?’”
Now he has a point. Writers for thethirdcity.org do make bank. But I figured the promotion should include a raise.
So I pressed him.
“Benny, this is the second promotion I’ve had in less than a year. You said your self, I’m doing good work. I want a raise.”
“You want a raise? Let’s see what Milo has to say about it,” he said as he picked up the phone and dialed.
After a few seconds, Milo picked up.
“Hey, Milo, fuck face here says he wants a raise. What do you think?”
He listened quietly for a good 30 seconds and nodded intently. Meanwhile, I tried to figure out how the hell Milo knew he was referring to me when he said “Fuck face.”
As he hung up he said:“Milo says fuck you. No raises for crazy Puerto Ricans.”
“That’s bullshit,” I said.
“Just consider yourself lucky to be getting this second premotion after that stunt you pulled last time.”
“Hey, I said I was sorry. It wasn’t my fault.”
“Not your fault? You drove the company Rolls Royce into Wrigley Field. You were actually on the field with the car.”

The company Rolls Royce….
“But, Benny….”
“When the cops got there they found you and six scantly-dressed women running the bases, laughing hysterically.”
“Benny….”
“In the car they found a case of champagne, six half-smoked joints and a baggy of coke in the glove compartment.”
“But it wasn’t….”
“You were running around in your thethirdcity.org boxers, Rolando. You‘re lucky we didn‘t fire your ass. Get the fuck out of here, asshole.”
I decided to let it go. I was fine with what I was making. But I still wanted to argue my case on what happened the last time.
So before I left I blurted out as quickly as I could manage: “All that wouldn’t have happened if Milo hadn’t thrown such a sick ass party, invited those fine ass ladies and hooked me up with his connect, Nickle Bag Bernie, and gave me the keys to Royce.”
“Get the fuck out of my house you damn maniac,” he screamed.
I ran out of his house as he hurled obscenities at me. I made it out of the door just as he was shouting: “Stupid Puerto Rican.”
Whatever. I got my job back. I’m making descent bank. Can’t complain.
Now if I can just get my hands on those keys to that Royce….
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Randolph Street: Back To Jail
These images are from a photo essay at Cook County Jail–1973.
All photos © Jon Randolph.
jonrandolph.com
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