Letter From Milo: Facebook Games

February 16th, 2020

A few months ago, Big Mike, the Barn Boss of this scabby, befuddled outfit, asked Benny Jay and I to attend a meeting in the conference room of our Michigan Avenue corporate suite. He wanted to discuss the sorry state of The Third City’s finances. According to the spread sheets Big Mike had tacked to the walls, readership was down, advertising was down, interest was flagging and, worst of all, revenues were nearly non-existent.

“Boys, we’re in trouble,” Big Mike said. “Unless we find more readers and crank up our cash flow, you two might have to take salary cuts.”



“But I’ve got the solution to our problems, “Big Mike continued. “We’re all going to get on Facebook.”

“Great idea, Big Mike,” Benny Jay said. “That’s why you’re the Barn Boss.”

“Good thinking,” I added. “But, ah, what the fuck is Facebook?”

“Facebook is a social networking site.”

“What’s networking?” I asked.

“Networking is something people do to stay in touch with like-minded individuals. They help each other find jobs, romantic partners, etc.”

“Sounds like a bunch of homely, unemployed losers fucking around on the internet.”

Big Mike called me a few choice names and then went on to explain our Facebook goals.

“The thing to remember,” he said, “is that we’re going for quality over quantity. We want to befriend movers and shakers, people in the media, people who can help promote The Third City. Don’t waste time making friends with just anybody. The whole point of this exercise is to promote our blog site and get obscenely rich. We’ll get together next month and evaluate our Facebook progress.”

When I got home that evening I poured a big glass of wine and sat down at the computer, ready to join the world of Facebook. To be completely honest, I actually had heard of Facebook before, but always figured it was something for kids. Not knowing any better, I imagined that an adult spending time on Facebook was odd, even creepy, sort of like a grown man spend time watching MTV. I quickly learned different.

Anyway, once I logged on to the site, I discovered that I needed help. So, I called on the services of the Facebook experts in my home, my daughters, Nadia and Petra. They quickly got me set up and explained the basics. The only thing lacking was a photo of me.

“Why do I have to put up a picture of my ugly old ass?”

“Duh, Dad, it’s called Facebook for a reason.”

“I’ve got an idea. Let’s put up a picture of Steve McQueen and tell everybody it’s me.”

“That would be, like, false advertising. Don’t worry, Dad. We’ll find a nice picture of you.”

The girls rummaged through some old photo albums and found a 20-year-old picture of me. They scanned it, did a bit of Photoshop work, and imported it into my Facebook profile. I was in business. Two minutes later, someone sent me a message asking to be my friend, and I was off to the races.

Every night I would sit at my computer, a couple of bottles of red wine in easy reach, and do my Facebook duty. I’d request friends, confirm friends, comment on links, become a fan of sites and post shit on my wall. I wasn’t doing it because I enjoyed it. No. If anything, it was becoming a chore. I was doing it for a greater good. I was doing it for The Third City. I was doing it for all the people that counted on us to keep their spirits up in these desperate times. I was doing it for all the good folks that see us as a bastion of decency and civilized discourse in an increasingly rude and hostile world.

Mainly, though, I did it until the wine ran out. I was usually as drunk as a pre-rehab Mel Gibson by the time I logged off of Facebook.

About a month later, Big Mike, Benny and I reconvened in our corporate offices.

“Well, boys,” Big Mike said, “we’ve staved off disaster. We live to blog another day. Our readership has increased by 38.4%. And it’s all due to Facebook. But, I have to tell you, I’m puzzled.”

“Why’s that?”

“If you remember, I asked you both to befriend movers and shakers, people with influence in the world of media and communications. Well, according to my printouts, you two did no such thing.”

“We did our best, Barn Boss,” Benny Jay said.

“Benny, the only people you befriended are Bulls’ fans and the guys on your bowling team, and most of them are illiterate. They need a calculator to keep score at the bowling alley.”

“What’s your point?”

“And Milo, you’re a disgrace.”

“So, what else is new?”

“I checked your friends’ list and the only people on it are young women who show a lot of cleavage in their profile photos.”

“It’s still a work in progress, Big Mike.”

“On top of that, you’ve become a fan of Madame LaFarge’s Whorehouse, Manny’s Pool Room, two off-track betting parlors and a guy named Nickel Bag Bernie. Who’s that?”

“Ah, let’s just say he’s an old and dear friend.”

“Whenever you comment on someone’s link, the only thing you say is ‘Go fuck yourself.'”

“That can’t be right.”

“And who’s this Elaine Soloway broad?”

“I’m not sure. I believe she was my third or fourth wife.”

“Well, I guess it’s not important. What matters is that our readership is up and the dough is rolling in again. Now, have either of you ever heard of something called My Space?”

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Letter From Milo: Annie & Willie

January 23rd, 2020

It was late Sunday morning and I was sitting at the kitchen table, drinking coffee and trying to write a blog piece that was due the next day. It was going to be the greatest blog piece ever written, one that would change the fate of the world.

You see, the evening before, while deep into a bottle of Jack Daniels, I had one of those revelatory visions that very few people have the great fortune to experience. In a moment of absolute clarity, I had discovered the secrets to solving world hunger, the economic crisis and the Arab/Israeli conflict.

Unfortunately, I had neglected to take notes.

That Sunday morning, as I was hunched over a yellow pad, desperately trying to reconstruct my brilliant ideas from memory, the lovely Mrs. Milo walked into the kitchen and said, “Milo, honey, are you going to mow the lawn today?”

“Hadn’t planned on it.”

“The lawn’s starting to look pretty bad..”


“The neighbors might start complaining about it soon.”

“Fuck the neighbors.”

“Oh, quit being such a grouch.”

“I’m not a grouch.”

“Yes, you are. You’re always grouchy when you have a hangover.”

“What makes you think I have a hangover?”

“You always have a hangover.”

I decided not to argue with the missus. As I mentioned before, she’s got a mean streak. It’s not a good idea to argue with her in the kitchen, where there’s cutlery in easy reach.

As I was mowing the lawn, I wondered if all writers had to put up with this sort of shit. Did Anne Hathaway interrupt William Shakespeare while he was writing Macbeth and tell him to go out in the pasture and shear a couple of sheep? Did Mrs. Hemingway interrupt Ernie while he was writing The Sun Also Rises and ask him to run down to the corner and pick up a baguette? Did Mrs. Stiglitz interrupt her Nobel Prize winning husband, Joe (arguably Gary, Indiana’s third or fourth greatest writer), and ask him to wash the car? I doubt it!

When I went back into the house, I told my wife exactly what I had been thinking. She stared at me in disbelief for a few moments then burst into laughter.

“If you’re comparing yourself to Shakespeare, Hemingway and Joseph Stiglitz, then you really have lost your mind. I doubt if there’s 10 people that read The Third City blog. The only money you’ve ever made from it is when you cheated your old friend, Tony Patellis, out of 20 dollars with that ridiculous fund raising scam.”

“Wait a damn minute! Big Mike and Benny Jay have personally assured me that we have a lot more than 10 readers. We’re huge in the New Hebrides.”

“Benny Jay and Big Mike are even bigger idiots that you are.”

“Damn it, Sharon. I don’t want to argue with you. I’ve got to finish this blog. It could be the finest blog piece ever written. It’s about world hunger, the economy and…”

“Okay, go finish your blog. But can you fix the screen door first? It’s sticking again.”

“Didn’t you hear what I just said?”

“It’ll only take a few minutes. Just do it.”

It took a lot longer than a few minutes to fix that fucking screen door. The cost in blood and sweat was dear, too. I gashed my hand with a screwdriver and nearly lost an eye when a drill bit snapped and bounced off of my forehead.

Somehow I survived and made it back to the kitchen table where my writing tablet and pens were waiting. Sadly, the thread of the idea for my great blog piece had unraveled. I could not recall the great breakthrough I had made in the wee hours of the previous evening. The world would have to limp along without my help, wallowing in the mire of hunger, economic instability and never-ending armed conflict.

And it was all my wife’s fault.

Still, I couldn’t give up on the blog bit. The writers of The Third City blog are blooded veterans of the QWERTY wars. Big Mike, the Barn Boss of this scabby, hygienically-challenged outfit is meaner than a wolverine. Benny Jay is tougher than a pack of pit bulls. And I’m meaner and tougher than both of them.

Besides, the world is counting on us. People all over this planet are relying on The Third City to provide the leadership, common sense, and compassion that they can’t get from their elected leaders. In essence, the world knows that The Third City may be its last and best hope. We are the caped crusaders of the blogosphere.

The ideas of the previous evening began coming back to me in dribs and drabs. I was beginning to reconnect the dots that would restore harmony to this sorely abused planet. Maybe I could salvage the situation. Maybe all was not lost. I had just starting jotting down some notes when my wife walked through the kitchen toward the back door, on her way to teach a Pilates class. Just before she closed the door behind her, she said, “If you get a minute, will you start the laundry?”


That, my friends, was the last straw. I was a broken man, defeated, with nothing to look forward to but pain, despair and a lingering death. When my wife came home, later that evening, she took a knowing look at me, shook her head, and said, “Will you do me a favor, honey?”

“What the fuck do you want now?”

“Will you be a dear and open a bottle of Pinot Noir?”

“Now, you’re talking, babe! Maybe I’ll open two.”

Maybe there is hope after all.

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Letter From Milo: Bank Robber

January 15th, 2020

I wasn’t always a famous, wealthy and beloved figure in the blogging world.

I know it’s hard to believe, but before I was overwhelmed by fame, fortune and the paparazzi, I was just a regular guy. By regular guy I mean I was an average Joe, shuffling along in obscurity, content to make a living, raise a family, get drunk once in a while and get laid on occasion.

Then, the feces got into the central air. Like regular guys everywhere I got hit hard by the Great George Bush Economic Meltdown. The small business I had owned and mismanaged for many years, the Dumbass Advertising Corporation, Ltd, LLC & Sons, nearly went under. The cash stopped coming in. The lovely Mrs. Milo had to shoulder the main burden of keeping us afloat. I had to do something, anything, to crank up the cash flow.

So, I got a night job.

It wasn’t a great job. I had never done anything like it before. I won’t even mention what it was except to say it wasn’t anything I’d care to post on my resume.

The best thing about it was the hours, six hours a night, four days a week. It allowed me to keep my normal activities going during the day and it provided much needed cash. It was what I needed at the time.

The business wasn’t exactly a fly-by-night enterprise, but it was real close. The workforce was a mixed bag of characters. There were middle managers who had been downsized, college kids working their way through school, retirees who couldn’t make it on their pensions, whores who were too old to make a decent living, a number of young men with crude jailhouse tattoos, musicians who had wasted their youths trying to get record deals, a few people who were obviously junkies, and of course, an aging, burned out advertising man.

It seemed that anyone who wanted that job could have it. The only requirements were the ability to read and write and minimal computer skills. None of the employees stayed long. Turnover was ferocious. After a month there were only two of us left out of a group of 12 that started with me.

The other guy was a man named Teddy, who, as a young man, had made a living as a bank robber in Mississippi.

Of course, he didn’t blurt out this information at our first meeting. We had to become friends first. And that wasn’t easy. I wasn’t looking for friends and I doubt if Teddy was, either. All we were looking for was a paycheck, preferably one that didn’t bounce.

But as new faces kept showing up week after week, and the people we knew drifted away, Teddy and I began spending more time with each other. We’d eat lunch and take smoke breaks together, and after work we’d walk to the El train together. Teddy generally carried a half pint in his jacket and had a drink or two on the walk to the train. He was a gentleman and always offered me a drink. And I always accepted.

It was while walking to the El one evening that Teddy said, “Man, you don’t know how good it feels to be walking down this street.”

“It’s a beautiful night.”

“It’s more than that, Milo. You see, I spent 22 years in prison, in Mississippi. Got out eight months ago. Just getting on this El train and going anywhere I want is sweet.”

“Damn, man. 22 years?”

“Yeah, robbed four banks. I should have stopped at three.”

When I got home that evening, I opened a bottle of wine, poured a hefty drink and thought about Teddy. I would have thought someone who had served so much prison time would be bitter and angry. But Teddy was just the opposite. He was one of the sweetest natured men I’d ever met, always smiling, always genial. I never heard him say a bad word about anyone. He even had a playful side, which he allowed me to see.

He had begun greeting me at work by giving me an ugly look and saying, “Motherfucker, where’s my money?”

And I’d reply by saying, “Spent it, motherfucker.”

Teddy always laughed at my reply and said, “Shit, man, I would have done the same thing.”

One evening as we walked to the El train, I asked Teddy, “It must have been tough being a black man in a Mississippi prison?”

“It wasn’t easy. The funny thing is that my own people made it tough on me. You see, most of the trustees and guards at the prison are black men. But they have to answer to white men. So they can’t look like they’re taking it easier on their own people than on whites. Motherfuckers can make your life miserable, sometimes.”

“How’d you get this job, anyway? The application form asked about felony convictions.”

“”They just asked if you had been convicted of a felony in the last seven years. Shit, man, I been in prison a lot longer than seven years.”

Another time, Teddy said, “Stolen money don’t last long. This short money we making here last longer than bank money. My biggest hit was $30,000 and it was gone in a month. Course I had to split it with a partner. If you a criminal you got a lot of expenses. Plus, you get crazy with the money. When you work for your money, you watch it closer.”

About a month later, Teddy came in late to work, which was unusual. He never missed work and he was always punctual. He was also disheveled and smelled of alcohol, another unusual occurrence. He never drank at work.

“Are you okay, man?” I asked.

“My woman put me out. I had to move all my shit into my brother’s place.”

“Damn, man, that’s rough.”

“Bitch went crazy. Accused me of all kind of shit. I swear, Milo, I ain’t even looked at another woman since I been out of jail.”

About an hour later, Teddy abruptly stood up at his cubicle, raised his face toward the ceiling and hollered something I couldn’t quite make out. Then he rushed toward the exit door.

That was the last time I saw him.

Word on the street was that Teddy had broken parole, either a domestic dispute, something to do with a car or a concealed weapons charge. I was pretty sure he didn’t go back to robbing banks because I didn’t read anything in the papers about any local banks being robbed. He might be in prison in Illinois or maybe they sent him back to Mississippi. Who the hell knows?

One thing I do know is that I miss him. He was good company and always cheered me up when I saw him.

Sometime in my life I’d like to see Teddy again. If I do, I’ll throw my arms around him, give him a big hug and say, “Motherfucker, where’s my money?”

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Letter From Milo: Mr. Exercise

December 31st, 2019

The other day my wife got on my ass about the state of my physical fitness, or rather, my lack of it. I had just awakened from a pleasant afternoon nap when the lovely Mrs. Milo came home after a hard day of selling real estate, lunching with her slutty girlfriends, and teaching Pilates classes.

“Have you been lying around in your underwear all day?”

“Ah, no, dear. I was just in the process of…”

“I wish you’d be more active. You’re starting to look sloppy. You need to start exercising once in a while.”

“I took a nice walk today.”

“Yeah, I know. You probably walked down to Swillagain’s and spent the afternoon drinking with all the bums that hang out there.”

“That’s a harsh thing to say. I know for a fact that two of the guys have regular jobs.

“Since when is pot dealing considered a regular job?”

“So, what’s your point?”

“The point is that you’ve got to start taking better care of yourself. You have to start exercising. I don’t care for you that much anymore, but your daughters are still somewhat fond of you. They wouldn’t mind having you around for a few more years.”

“Okay, sweetie, I’ll give it some thought.”

Physical fitness is important to my wife. When I first met her she was a touring dancer, in as good a shape as it’s possible for a human to be. Dancers take strenuous, exhausting classes every day, and often put on even more tiring performances those same evenings. They have to stay in shape. Their bodies are their instruments. I doubt there are many people on this planet, aside from professional athletes, who are in better shape than professional dancers.

When my wife retired from dance, she had a hard time giving up the physicality of the dancing life. She tried taking an occasional dance class but old injuries – knee, neck, ankle – kept flaring up. She fretted for years about her physical conditioning. I mean, God forbid that she should gain a pound or two. Then she discovered Pilates, which, as I understand it, is something the Communists invented to replace sex. She liked Pilates so much that she became a Pilates’ teacher. Now she’s happy. She’s found a physical regimen that can keep her busy and in great shape until she’s 112 years old.

One the other hand, I don’t give a rat’s ass about exercise, physical fitness or anything else that distracts me from the important things in life, like drinking, smoking, drug abuse, eating red meat and entertaining impure thoughts.

That said, I know my wife will make my life miserable unless I start some sort of fitness program. And once the kids start in on me, well, let’s just say things will get interesting, in the Chinese sense of the word.

So, the next afternoon I went down to Welles’ Park, a Chicago Park District Fieldhouse on Sunnyside by Lincoln Avenue. They have a well-equipped gym there which, since I am of a certain age, I can use for free.

The guy behind the counter was a typical Chicago Park District employee – gruff, overweight, with a pack of smokes in his shirt pocket. I thought I smelled liquor on his breath, too, but I wouldn’t swear to it. After I filled out the paperwork and received a laminated Welles’ Park membership badge, the guy offered to show me around the fitness area.

“You ever use any of this shit before?” he asked, pointing out all of the exercise equipment.

“Can’t say that I have. What’s that?”

“That’s called a stationary bike. You gotta watch yourself on that thing. We had a regular customer, used to come in four or five times a week. He’d ride that thing nonstop for an hour. Last week he was riding on it and just keeled over.”

“Was he okay?”

“Fucker died.”

“That’s too bad. How old was he?”

“About your age.”


“That’s a treadmill over there. It’s like a walking machine. A couple of months ago a guy was on it and had a heart attack. He died, too.”

“How old was he?”

“About your age, I guess.”

“What the fuck!”

“That thing over there is a rowing machine. Last month a guy…”

“Don’t tell me. He was about my age, right?”

“No. I believe he was a bit younger than you.”

I had heard enough. I handed the Park District guy the laminated badge and said, “You can take this badge, give it back to Mayor Daley and tell him to stick it up his fucking ass. This place is a death trap. I’m getting the fuck out of here.”

I was a bit shaky when I left Welles Park. There’s no telling what terrible things would have happened to me if I had stuck around and tried a few exercises. Fortunately, I had to pass Swillagains on the way home, so I stopped in for a few drinks and enjoyed a hand-rolled smoke with my friend, Nickel Bag Bernie, just to calm down.

When I got home, a few hours later, I was in the physical and mental shape that I prefer above all others. The lovely Mrs. Milo, sipping a nice white wine, was waiting for me. “Well, how did it go?” she asked.

“How did what go?”

“Your trip to Welles Park.”

“It went okay.”

“Did you try any of the equipment?”

“Let’s say I checked things out.”

“So, do you feel any better?”

“Honey, right now, I feel great.”

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Letter From Milo: Toilet Prose

December 17th, 2019

Early on I discovered that I could not move my bowels unless I had something to read. There seems to be a direct connection between my eyes and my ass, a sort of optical/lower intestinal tripwire that, once engaged, releases the fecal floodgates.

The problem with being a shithouse reader is that I tend to spend more time in the bathroom than is absolutely necessary for conducting my, ah, personal business. Now, most reasonable people would consider bathroom reading to be a harmless habit, like farting at inappropriate times. Unfortunately, I am surrounded by unreasonable people — my family.

You see, over the years I’ve had the misfortune of acquiring a mean, hot-tempered, violence-prone wife and two spoiled, ungrateful daughters. Still, despite their obvious failings as spouse and offspring, I’ve grown to tolerate their presence. I have even become somewhat fond of them. Most of the divisive issues that have plagued my family – smoking, drinking, drug abuse, gambling, etc. — have been solved or made peace with years ago. The one issue that has never been properly settled is access to the bathrooms.

Regretfully, I am a man of modest means. Due to a lack of skills, ambition, and a spotty employment history I can only afford a home with two bathrooms. And, as I have painfully learned, having a home with more occupants than toilet facilities is a situation that often leads to some rather “frank but encouraging discussions,” as diplomats tactfully phrase it.

“Dad, are you in there?”


“You’ve been in there a long time. What are you doing?”

“I’m taking a dump. What do you think I’m doing?”

“No you’re not. You’re reading one of your stupid books.”

“God damn it, can’t a man take a shit in peace around here.”

“Quit hogging the bathroom.”

“You ungrateful brat, go use the upstairs bathroom.”

“Mom’s using it.”

“Then go pester her and leave me the fuck alone.”

“I’m telling Mom you’re cussing at me again.”

At the time, I was probably reading James McManus’ “Positively Fifth Street,” a wonderful book that’s held a place of honor in my bathroom book stack for a long time. As McManus himself put it, becoming bathroom reading material is, “…one of the highest honors a book can achieve.”

Other books that have held places of honor in my bathroom for long periods of time are, “Drinking, Smoking & Screwing,” a anthology edited by Sara Nickles, “A History of Torture,” by George Riley Scott, “Straight Life: The Story of Art Pepper,” by Art and Laurie Pepper, “The Collected Stories,” by Isaac Bashevis Singer, “Fanny Hill,” by John Cleland, “Down and Out in Paris and London,” by George Orwell, “Class,” by Paul Fussell, just to name a few.

The secret to good bathroom reading material is that the books have be easy reads yet compelling, with passages that you want to read over and over again. I doubt that many people have James Joyce’s works stashed in their lavatories, although I’m sure there are a few professional Irishmen who have dog-eared copies of “Ulysses” or the collected works of Samuel Beckett stacked up next to the toilet paper roll. That’s why I always…

“Dad, are you in there?”

“What do you want?”

“I need to use the bathroom.”

“Damn it, can’t you see I’m using it.”

“You’ve been in there a long time. You’re probably just reading some dumb book.”

“Why don’t you try the upstairs bathroom?”

“Nadia’s using it.”

“Jesus Christ! Show some fucking initiative. Go down to the corner and use the gas station bathroom.”

“Dad, I can’t believe you said that.”

“I suggest you avoid the Citgo and go straight to the Mobil station. Bring your own toilet paper.”

One of the newest additions to my shithouse library is the “U.S. Army Survival Manual.” This is a terribly written book, probably put together by a group of barely literate PFCs in the Pentagon basement. The book offers all sorts of incomprehensible advice on how to survive horrible situations, like being lost in a jungle or marooned on a desert island. It tells you how to trap animals for food, find edible plants, build shelters, start fires, and locate drinking water – all written in stiff, government-issue prose that has me yawning after a couple of paragraphs.

The only reason I like the book is that it has a section on poisonous snakes that I find fascinating. It has several dozen color plates of poorly photographed venomous serpents and offers advice on how to avoid them, how to treat snakebites and how to kill, butcher and eat them. This is very useful information. If I ever run into a Gaboon Viper or a Black Mamba on the streets of Chicago, at least I’ll be prepared to…”

“Milo, are you in there?”

“Yes, dear.”

“The girls tell me you’ve been cursing at them again.”’

“Heh, heh, perhaps they misunderstood me. The acoustics are lousy in this part of the house.”

“Did you tell Petra to go use a gas station bathroom?”

“Now, now, dear, you know the girls have overactive imaginations.”

“Have you been drinking today?”

“Of course not.”

“Are you telling the truth?”

“Honey, have I ever lied to you?”

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Letter From Milo: Ad Man

December 8th, 2019

I was awakened from a sound sleep, about three in the afternoon, by a phone call from Big Mike, the Barn Boss of this scabby, talentless blogging outfit. The Barn Boss sounded uncharacteristically agitated.

“Milo, we’ve got a problem.”


“This time it’s serious. The Third City is broke.”

“Jesus! How can that be? When you hired me you said we had hundreds of thousands of readers.”

“Well, heh, heh, I may have exaggerated a bit.”

“How many readers do we actually have?”

“Ah, seven.”

“Seven! You’re shitting me.”

“Well, I’m still waiting for the numbers to come in from New Zealand. But, never mind that. The point is that we’re in a jam and the only way out is by advertising. We’ve got to sell ads on our site.”

“What kind of idiot would even consider advertising with us?”

“I’ve given it a lot of thought. See, advertising is a lot like writing. You write about things you know. In advertising, you sell ads to people you know, people you do business with on a regular basis, people whose products and services you buy.”

“I guess that makes sense.”

“Right now, Benny Jay is out on the street selling ads to all the fried chicken joints and Chinese restaurants in town.”

“Benny does like his chicken.”

“So, all you have to do is visit your favorite business establishments and sell them ads. Trust me, it’ll be a piece of cake.”

“Okay, I’ll give it a shot.”

I had spent quite a few years in the ad game, and I had hoped never to go back to it. I worked as a copywriter and creative director for several small and midsized agencies. I was a professional bullshitter, the person who comes up with catchy headlines and informative copy that are supposed to convince you that the products or services I’m writing about are things you can’t live without. I was, in essence, a salesman with a keyboard.

I’ve met a lot of interesting people in the advertrising world. The industry is filled with talented, driven, ambitious people who could succeed in almost any other fields they set their minds to.

On the other hand, I’ve also met a lot of raging assholes, unscrupulous people who were either borderline psychotics or shameless thieves. Sadly, the ad game seems to attract nutcases. It is an industry driven by creativity, the almighty dollar and merciless deadlines, a combination that’s guaranteed to bring out the absolute worst in people.

Still, as much as I hated getting involved in advertising again, I owed it to Big Mike and Benny Jay to help keep The Third City going. Besides, Big Mike was right. If I stuck to soliciting business from people and companies I knew, I figured I could sell a few ads and keep this fine blog site afloat.

A phone call from Big Mike woke me up the next afternoon.

“Well, how’d you do?”

“About what?”

“Selling ads, asshole.”

“Oh, I did real good. Sold three ads.”

“That’s great, man! I knew you could do it. Who’d you sell ad space to?”

”I sold one to Nickel Bag Bernie…”

“The pot dealer?

“Yeah, he wants to expand his business.”

“Ah, okay. How much did you get?”

“50 bucks.”

“Jesus, that’s great. We can use that 50 bucks.”

“There’s one little hitch, though. Bernie got in a new shipment of fine weed from Hawaii.”


“I bought a quarter ounce for a hundred bucks.”

“Are you saying that you sold an ad and lost 50 bucks on the deal?”


“Great fucking job.”

“Thanks. After I left Nickel Bag Bernie’s I stopped by Madame LaFarge’s Whorehouse and sold her an ad for 100 bucks.”

“That’s more like it.”

“Except, there was another little hitch.”

“Oh, Christ!”

“You see, Madame LaFarge hired a new girl, a cute little thing from Sri Lanka. She’s double jointed and does this weird thing with her hips that…”

“How fucking much?”

“250 bucks, plus a tip.”

“Let me get this straight. You sold Madame LaFarge an ad and only lost 150 bucks on the deal?”

“Plus the tip. Then I stopped at Swillagain’s and sold an ad for 25 bucks.”

“Don’t tell me.”

“Well, I had few drinks, then bought the boys a round…”

“I get the picture.”

“By the way, how did Benny Jay do selling ads to fried chicken joints and Chinese restaurants?”

“I don’t know. He’s still in the hospital getting his stomach pumped.”

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Letter From Milo: Troubling Mistress

November 13th, 2019

It must be contagious. Mistresses all over the world are coming out of the woodwork and revealing their affairs with famous married men. You can’t open a magazine or newspaper, get on the internet, or watch a TV talk show without reading or hearing about yet another woman claiming to have frolicked with a well-known, wealthy and very wedded man.

The reason that all of these mistresses are coming forward is, of course, the almighty greasy dollar. Magazines and TV shows routinely write huge checks to any woman willing to dish the dirt on a married celebrity. For many mistresses of the rich and famous, this has become something of a retirement plan, sort of a mistress IRA.

Tiger Woods and Sandra Bullock’s husband, Jesse James, are two of the most recent victims to be pilloried in the pages of People, US Weekly, Star and other check-out line publications. It breaks my heart to see fine young men like Tiger and Jesse having their good names and stellar reputations being dragged through the mud. And for what? All they were doing was what any other red-blooded American male would do, given the opportunity. After all, cheating on your wife is as American as apple pie (apologies to H. Rap Brown).

Poor Tiger even had to undergo the time-honored charade of calling a press conference and blatantly lying to the world about how sorry he was for nailing all that fine pussy.

Any real man will tell you that the only regret Tiger has is that he didn’t nail more women before he got busted.

Sadly, mistress trouble isn’t restricted to movie stars and athletes. Even famous and wealthy bloggers, like those of us at The Third City, can be led astray.

In our case, the feces has, indeed, gotten into the duct work. According to Leopold & Loeb, our attorneys here at The Third City, several of my mistresses have decided to rat me out. Apparently they can’t resist the fat checks that the Chicago Reader, the Ravenswood Homeowners’ Association Newsletter, the Wicker Park Shopper & Coupon Book and WXRT are offering.

This news couldn’t have come at a worse time. My wife and I are at a delicate stage in our marriage. The other day I caught her Googling Family Therapists. I have a hunch she’s going to drag my ass off to marriage counseling again. Feeling just a touch of a panic, I called Big Mike, the Barn Boss of this scabby, flatulent and barely literate blogging crew and asked his advice.

“Hey, Big Mike, it’s me, Milo.”

“Make it quick, asshole, I’ve got a blog to run.”

When I explained the problem to the Barn Boss, he sighed deeply and said, “Shit, Milo. I’ve got the same problem, my girlfriend, Coco LeFarge, is threatening to go to the media unless I buy her a new Mercedes.”

“That sucks. What are you going to do?”

“I don’t know. Maybe she’ll settle for a new Chevrolet.”

“That should do it.”

Benny Jay’s girlfriend is giving him a bad time, too.”

“That’s a shame.”

“She claims Benny’s spending way too much time and money on his other girlfriend. If Benny’s wife finds out she’ll kill him.”

“Yeah, Benny’s wife has got a mean streak. But what am I supposed to do about my three mistresses?”

“Well, we’ve got to have a plan to deal with all these ungrateful women. You and Benny come down to The Third City corporate office on Michigan Avenue tomorrow morning and we’ll…”

HOLD IT! This is Mrs. Milo. I just noticed what Milo was writing and threatened to mace him if he didn’t get away from the computer immediately. He is SOOOO full of crap. Here he is, looking and smelling like a sick dog, sitting around in a ratty bathrobe, hasn’t shaved or showered in a few days, plus, he’s still half drunk from all the wine he drank last night, and he’s bragging about what a ladies’ man he is. Three mistresses! I’d laugh if it wasn’t so pathetic. Listen, any women that wants his worthless old ass can have him. I should have dumped him a long time ago. I’d trade him in for a new washer and dryer right now.

Those two idiots that Milo associates with, Big Mike and Benny Jay, are almost as bad as he is. I doubt if there are three uglier or less appealing men in the City of Chicago. They’re just three over-the-hill burnouts with nothing better to do than write those stupid blogs. They’re lucky if they get six or seven people to read their nonsense. The corporate office they talk about is actually the Sanka House, the low-rent coffee shop on the corner. Swear to God, if either of them so much as approached a woman, the poor thing would probably call 911. Jeez, what a bunch of losers.


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