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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Letter From Milo: Auto Theft

November 6th, 2019

I haven’t stolen any cars in the last few years, but I’m planning to steal one this weekend. This is going to be a tricky theft, one that’s going to take cunning, nerve and brass balls. The car in question is a rare vehicle, prized for its symbolism as much as its transportation value.

To do this job right I’m going to need a partner, someone ruthless, meaner than a snake and without a shred of conscience. I need someone who is heavily armed and willing to resort to violence, someone who won’t faint at the sight of blood. I want some serious muscle on my side in case things get ugly. My partner has to be cruel, nasty, devious and cunning. Fortunately, I found the perfect accomplice, a savage cutthroat with a long and brutal criminal history.

It’s my sister.

And the car we’re going to steal belongs to my 85-year-old mother.

Now, technically, we’re not actually going to steal my mother’s car. What we are doing is taking the car away for her own good. At least that’s what my sister tells me.

“She’s a menace. Her mind is slipping. Her doctor told me she shouldn’t be driving. And that was a year ago.”

“I don’t know. She loves that car.”

“I’m telling you, she’s dangerous. What if she gets in an accident and kills herself?”

“At least she’ll die in the saddle.”

“Even worse, what if she runs over some kid playing in the street?”

“Teach the little fucker a lesson about playing in streets. He’d be better off hanging out in a pool room like a regular kid.”

“Sometimes you sound like an idiot. Are you drunk?”

“Ah, not yet.”

I’m well aware that my mother’s mind is slipping – and it’s breaking my heart.

She used to be as sharp as Joseph Stiglitz, but time has eroded her keen faculties. Now she’s inching toward the Shemp Howard end of the gray matter scale (no offense, Mom). As much as I hate to say it, sometimes having a telephone conversation with the dear old lady can be a chore.

“Is your furnace okay?


“Your furnace. You know it’s very cold outside.”

“The furnace is fine, Mom.”

A few minutes later…

“Is your furnace okay? Maybe you should have it checked.”

“Mom, you already asked me about the furnace.”

“I did? Is it working okay?”

“Works real good, Mom.”

“That’s a relief.”

Another few minutes later…

“Have you had your furnace checked recently? It’s very cold outside.”

Ever since the Old Man packed his bags and checked into Graceland, more than 20 years ago, my mother has relished her independence. She lives in a small apartment about a quarter mile from my sister in Munster, Indiana. Although my sister regularly asks my mother to move in with her, Mom always refuses. She loves her little apartment. She likes the freedom to do whatever she wants and not have to answer to anyone. She says she enjoys the peace and quiet (the Old Man had an aggravating fondness for the Old Rip ‘n Roar). Mostly, though, she likes to get in her car and drive. “As long as I can drive,” she says, “I can take care of myself.”

The car is more than a means of transportation to her. It is a symbol that allows her to believe she is still a strong and vital woman, someone who lives her life according to her own rules. The sad truth is that she can no longer maintain that fiction. She is now a little old lady who needs help.

The next thing to consider, of course, is her housing situation. Soon she’ll have to give up her apartment and move into some sort of housing for the elderly. My sister has already been researching Assisted Living facilities. She found one not too far from her home and has begun negotiations.

My mother will, no doubt, put up a fight about giving up her apartment. She may not be as sharp as she once was, but she’s as feisty as ever. My sister and I will have to plan this next step in Mom’s life very carefully. This could very well be trickier than stealing her car. I just hope I don’t have to blackjack her, toss her in the trunk of my car and drive her to her new home in the middle of the night.

Ah, fuck it, might as well add kidnapping to my long list of felonies.

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Letter From Milo: Looking Very Good

October 15th, 2019

You can’t tell it by looking at me, but I used to be a very handsome man. There was a time when I had a full head of hair, all my teeth, a trim belly and fewer scars. Not only was I, arguably, the greatest writer ever to come out of Gary, Indiana, I was also, hands down, the best looking man ever to come out of that fine metropolis.

Inevitably, time has had its cruel way with me. I’m a shell of my former handsome self. Whenever I look in a mirror I feel a terrible sense of sadness and loss. I imagine Michelangelo felt the same way when the first cracks appeared in the ceiling of the Sistine chapel.

A great writer, whose name I don’t recall, once said, “By the age of 50, every man has the face he deserves.” If that’s the case, what the fuck did I do to deserve this?

The reason I’m bringing up this subject is that I’ve recently been under a lot of pressure to get on Facebook. Big Mike, the Barn Boss of this scabby, barely legal outfit, has been especially tough on me about Facebook. After dozens of abusive emails and several threatening letters from The Third City’s attorneys, I decided to give Big Mike a call.

“Hey, Big Mike, it’s me, Milo.”

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

“What’s this shit about me getting on Facebook?”

“We need more readers. My investors are getting antsy. There’s a lot of Arab and Japanese money behind this blog site.”

“When you hired me you said we had, like, 15 million readers a day.”

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

“How many readers do we actually have?”

“Seven. But I haven’t got the numbers in from Europe and Asia yet.”

“Seven! That’s it!”

“Yeah, but we can easily double that number if you get on Facebook.”

“Ah, okay.”

Which brings me back to the beginning of this blog. You see, according to my daughter, who set up my Facebook account, I had to have a photo of myself on the site. But I was hesitant about posting a recent photo because, as I had mentioned, my present appearance is not up to my usual lofty standards.

There you have it. My daughter went through some old photo albums, found a 25-year-old photo of me, scanned it, doctored it up, and posted it on the site.

So, if any of you ladies are thinking of contacting me for a little fun and games, you might want to think twice about getting in touch. Instead of spending quality time with a young Al Pacino, you’d end up frolicking with an aging Bela Lugosi.

Don’t say you haven’t been warned.

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Letter From Milo: Bag Man

October 6th, 2019

A few years ago I started carrying a shoulder bag. I had been considering getting a shoulder bag for a long time, but there was something keeping me from getting one. That something was stupidity.

You see, I always thought that carrying a shoulder bag was an affectation, something a real man would never do. A shoulder bag, it seemed to me, was a sure sign of effeminacy. I mean, how much shit did a person have to haul around? You had your wallet, keys, cash, cigarettes and lighter, half pint of whiskey, extra-large, industrial strength condoms, and perhaps a concealed weapon, generally a straight razor or snub-nosed pistol.

All of those things could easily fit into the four pockets that traditionally come with a pair of pants in the Western World. Anything else was just extraneous bullshit.

But as time went on and life got more complicated, I found that four pockets were no longer enough to contain the things I had to carry around on a daily basis.

For example, when I got hired by Big Mike, the Barn Boss of the scabby, hygienically challenged crew that writes for The Third City, I had to start carrying notebooks and pens to write down the great thoughts that occur to me on a regular basis. And how was I supposed to haul around my paperback books, crossword puzzle books, sunglasses, vials of uppers and downers, bags of weed and other necessities of life? There was no way all of that crap could fit in my pockets.

As much as I hated to do it, it was time to get a shoulder bag.

The first bag I got was a funky old canvas bag that I found at a thrift shop on Roscoe Avenue. It cost about three bucks and served my purposes admirably. The problem was that it was an ugly old thing, covered with stains and falling apart at the seams. When my wife, the lovely Mrs. Milo, saw it she started laughing.

“Do think you could have gotten a nastier looking bag?”

“What’s wrong with it?”

“It’s covered with spaghetti stains.”

“I’ll throw it in the washer.”

“It stinks, too. Smells like a cat peed on it.”

“That should wash out, too.”

“Honey, you can’t wash out ugly.”

A few weeks later, Mrs. Milo came home and presented me with a brand new, black leather shoulder bag.

It was beautiful. The bag was made of deep, rich cowhide that shone like patent leather. It smelled like the interior of a brand new Buick Electra 225. It had shiny snaps and buckles and it was roomy enough to carry all of my essentials. Best of all, it was a manly looking bag. There was not a hint of effeminacy about it.

I’ve never cared about fashion. To quote the great Howlin’ Wolf, “I dress for comfort, baby, I don’t dress for speed.” I always considered people who made a fetish of fashion to be shallow, frivolous individuals. With so many problems in this world, with so many evils and injustices to contend with, spending time thinking about what to wear is a huge waste of time. Spending great amounts of money on clothes strikes me as the height of irresponsibility.

That said, my new shoulder bag affected me in ways I would never have imagined. I started paying more attention to what I wore. I started paying attention to what other people wore. And if I saw someone carrying a shoulder bag, I immediately compared it to mine. I wasn’t turning into a fop, by any means, but I will admit that the potential was there. I was becoming a changed person, a Milo 2.0.

But some things never change. The other day my youngest daughter asked if I had a pen. I told her to look in my shoulder bag. After looking through the bag, she asked:

“Dad, why do you carry that ugly knife in your bag?”

“Well, honey, “I explained, “if you ever need to cut somebody up, a knife is a good thing to have.”

“I see,” she said, nodding in understanding. “By the way, Dad, can I have some money? I need to buy some new clothes.”

“Sure, sweetie. That’s money well spent. How much do you need?”

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Letter From Milo: There Goes The Nobel

September 29th, 2019

I did it again. I used this blog space to air personal grievances, which is strictly against corporate policy. Not only did I disparage Joseph Stiglitz, the esteemed Nobel Prize winner, but I also attacked Alfred Nobel, the hypocritical bastard who introduced dynamite to an unsuspecting world and then had the gall, the unmitigated audacity, to name a peace prize after himself. The man had brass balls. I bet you could have heard him coming a mile away.

Still, everything would have been just fine except that I made one little bitty error in judgment. I took one tiny step over the line. I made the mistake of calling Alfred Nobel a “Swedish cocksucker.”

Within minutes of posting that blog, our corporate office on Michigan Avenue was flooded with thousands of emails, phone calls, telegrams and faxes, all from outraged Swedes and all demanding my head. Here are a couple of the tamer missives:

“Yah, der is no sucking of cockers in Svenska. Dis bad man Milo is telling many lies.”

“Yah, I am understanding that there is much sucking of dicks in Norway, but, I am assuring you, it has never happened in Sweden.”

“Yah, Alfred Nobel is a true hero and a saint of my people. He would never think to shame his country by blowing somebody’s job.”

I thought the whole thing would blow over in a day or two. After all, what the hell do the Swedes have to bitch about? They’ve got themselves a nice little country up by the North Pole. They have a high standard of living, universal health care, a reputation for open-mindedness, good beer, safe cars and an abundance of long-legged, busty blonds. Despite foisting lutefisk and ABBA on the world, Swedes seem like decent folks.

Like I said, I thought things would settle down in a day or two, but I was wrong. That afternoon, I got an email from Big Mike, the Barn Boss of this scabby, lice infested outfit. When I opened the email I read the words:

“You are suspended indefinitely – without pay.”

Shit! I didn’t mind the time off, but I would dearly miss the money. I have a family to support, two mistresses with expensive tastes, plus six or seven child support checks to mail out every month. I need that money. I have a lifestyle to maintain. I have responsibilities.

So, I decided to call the Barn Boss and see if I could convince him to change his mind.

“Hey Big Mike, it’s me, Milo.”

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

“Damn it, why are you suspending me this time?”

“For one thing, you insulted the national hero of Sweden. We have tens of thousands of readers in Sweden. That country is a cash cow for us. Now the Swedish Parliament is going to revoke our blogging license.”

“It was just a lapse of judgment on my part.”

“Lapse of judgment my ass. What about the time you called the Queen of England an ugly old whore?”

“I had just come out of surgery. I was heavily sedated.”

“What about the time I suspended you for calling the Pope a senile old pedophile? Cost us a lot of Catholic readers.”

“I was drunk.”

“And that time you called Barbra Streisand a addle-headed, talentless slut? Cost us a lot of gay readers.”

“Okay, okay, I’m sorry. But this suspension without pay comes at a damned inconvenient time. I’ve got some expenses coming up. Can you loan me twenty bucks to see me through the week?


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Letter From Milo: Gary’s Greatest

September 16th, 2019

This guy, Stiglitz, is starting to piss me off. Just because he won a Nobel Prize in Economics he thinks he’s some kind of Big Shot. If you want to know the truth, the reason he turned to Economics was that he was a complete failure as a bookie in Gary, Indiana. All the good math students in Gary aspired to be bookies. Joe, unfortunately, couldn’t cut the mustard. When Bears and Bulls were mentioned, Stiglitz immediately thought of the stock market. What a huge waste of talent.

Anyway, the reason I’m pissed at Stiglitz is that he snubbed Benny Jay, my good friend and fellow blogger here at The Third City. You see, when we were having a raging debate on this site over who was Gary’s greatest writer, the esteemed Morry Frank, the immortal Monroe Anderson or the well-hung Milo Samardzija, Benny insisted on including Joseph Stiglitz in that distinguished group.

Benny even wrote a piece on the subject, saying that anyone who had been awarded a Nobel Prize should, at the least, be given some consideration for the title of Gary’s greatest scribe. After giving it a great deal of thought, while at the same time consuming a joint and a couple of bottles of wine, I grudgingly agreed.

After writing the piece, Benny decided to forward the article to Stiglitz, thinking that the “great” man would be flattered to be mentioned in the same breath with me, Morry and Monroe – at least that’s what Benny told me. But I know his real motivation. He just wanted to correspond with a Nobel Prize winner so that he could have something to brag about at fancy dinner parties.

“I just got an email from Joseph Stiglitz.”


“Joseph Stiglitz, the Nobel Prize winner in Economics and, arguably, Gary’s greatest writer.”

“You know the fucker?”

“Well, heh, heh, we’re not real close, but we do exchange emails on occasion.”

“What did he send you an email about?

“Nothing important. Just small talk. Mainly, we discussed, ah, the Bears and Bulls.”

Sadly, Stigliz never replied to Benny’s email. All he got was an automated response, saying that Stiglitz was available for personal appearances, speaking engagements, shopping center openings, Bar Mitzvahs, and throwing out opening-day baseballs. Further correspondence should be addressed to his agent.

That’s what you get for fucking around with Nobel Prize winners. Except for Saul Bellow and Mother Teresa, they’re mostly a bunch of elitist bastards with nothing going for them except a freakish sort of Rain Man intelligence.

By the way, did I mention that I hate the Nobel Prize? Well, not the Prize itself, just the man who endowed them, that low-life Swedish cocksucker, Alfred Nobel.

Alfred Nobel made his fortune by inventing dynamite, which, at the time, was the most powerful explosive known to man. Dynamite was responsible for killing untold numbers of human beings on battlefields all over the world. The death toll in World War I was appalling. Millions of people died in the last of Europe’s dynastic wars. And a huge amount of those deaths were directly attributable to Alfred Nobel’s diabolical invention.

I won’t even mention the toll that dynamite has taken on our planet. Check out some areas in Kentucky and West Virginia, where dynamite was used to level mountains and denude native forests in the frenzied search for coal. Some of those coal fields look like especially bleak parts of the moon.

After foisting dynamite on the human race, Alfred Nobel seemingly had an attack of remorse. He established the Nobel Prizes to salve his rotten conscience. And, get this, the most notable of the Prizes is the Nobel Peace Prize. What gall! What fucking nerve!

A peace prize from someone who has the blood of millions on his hands. Why not give Charles Manson a star on the Hollywood Walk of Fame while you’re at it.

Just thinking about that damned old dynamiter put me in a terrible frame of mind. I had to talk to someone to calm me down. I called Big Mike, the Barn Boss of this scabby, debt-ridden outfit.

“Hey, Big Mike, it’s me, Milo.”

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

“I just wanted to tell you that I’ve got my blog ready for Monday.”

“What’s it about?”

“It’s about the Nobel Prize.”

“What! Are you fucking nuts! Why are you writing about the Nobel Prize? Our numbers are down. You should be writing about porn, something that’ll bring our readers back.”

“Okay, I’ll write about porn next week. By the way, have you given any more thought to my request for a raise?”


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