Letter From Milo: Big Pimpin’

April 14th, 2014

There’s no Wi-Fi in the Cook County Jail, so I used my one phone call to contact Benny Jay, my partner here at The Third City, to explain why I wouldn’t be posting a new blog this week.

“Jesus! What are the charges?”

“I’ve been accused of violating the Mann Act, transporting a bunch of women across state lines for immoral purposes. It was a set-up. I was framed. They’re trying to say I was taking the women to Indianapolis to work the Shriners’ convention.”

“Isn’t that called ‘white slavery’?”

“Well, I had some black chicks in the van, too.”

“I’ve got a feeling this is going to reflect poorly on The Third City.”

“Benny, don’t worry about it. It’s all bullshit. The charges won’t stick. Next to drug dealing, trafficking in sex may be the most popular, and ignored, illegal business on earth. Nobody’s going to give a shit.”

If prostitution is the world’s oldest profession, then pimping is a close second, followed by the priesthood. From the moment humankind emerged from the mire, and women discovered they had something between their legs that drives men wild, there have been slick, fast-talking and ruthless bastards trying to make a profit from the female sweet spot.

Pimping isn’t what it used to be. The old business model – a guy wearing flashy clothes, driving a flashy car, running a small stable of streetwalkers – is becoming obsolete. The pandering business has changed beyond recognition. Old school pimps, like Iceberg Slim and West Side Wally Popovich, would be hard-pressed to make a living these days.

The big pimping money is in human trafficking, finding and transporting young women and girls from all over the globe to work in strip clubs, brothels, escort services, and satisfy the internet porn market’s insatiable demand for fresh young bodies.

A new breed of amoral character has evolved to meet the new pimping challenges. He’s no longer an opportunistic local boy, preying on the neighborhood girls, trying to find the ones who will fuck for money and give it all to him.

Now he’s an international player, often a member of an organized gang or cartel, traveling the world, exploiting impoverished young women and their desperate families. He’ll say or do anything to acquire new talent, promise glamorous jobs, marriages to kind, wealthy men, or educational opportunities. If that doesn’t work, the girls are sometimes kidnapped, or purchased outright, bought and paid for like livestock.

These new age entrepreneurs may have changed their recruiting methods, but some pimping techniques have never gone out of style. Once young women fall into their hands, pimps use drugs, isolation, intimidation and violence to control them.

The shelf life of a sex slave is generally pretty short. They get sick, become drug addicts, suffer physical abuse from pimps and customers, spend time in jail, run away, get killed, or kill themselves. Worst of all, from a pimp’s perspective, they eventually lose their looks, lessening their earning power.

That’s why a pimp with business savvy is constantly looking for new talent. He understands that a successful business man is one who rotates his stock, keeps his inventory young and fresh. And he’ll travel to the ends of the earth to keep his customers happy.

Some estimates say that as many as 30 million women a year are trafficked as sex slaves.

So, fellas, the next time you go to your favorite porn site to watch a young girl sucking cock, being gang-fucked, or taking it up the ass for your viewing pleasure, just remember, there’s a good chance she’s drugged, diseased, physically abused, scared to death, and a long, long way from home.

When they released me from jail, I went straight to The Third City’s plush Michigan Avenue office. When Benny Jay saw me, he said, “Oh, man, I’m glad you’re back. The place was falling apart without you. What happened?”

“They dropped the charges.”

“How did you explain driving a van filled with fine looking babes across the state line?”

“I told the judge I was a Mormon, on my way to a family reunion.”

“The judge fell for it?”

“Well, that, and an envelope stuffed with cash.”

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Letter From Milo: High Style

April 7th, 2014

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 as Society, Lifestyle & Religion columnist 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 check 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 handy 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: The Labors of Hercules

March 31st, 2014

We’ve got two bathrooms in our house, one upstairs and the other downstairs. My wife, the lovely Mrs. Milo, and our daughter use the upstairs bathroom. The downstairs facility is reserved for my use.

The other day, my wife asked, “When’s the last time you cleaned your bathroom?”

“I don’t know, maybe a month ago.”

“Honey, you haven’t cleaned the bathroom in at least six months. It stinks. Weird things are growing on the walls. I’m afraid to go in there.”

“I’ll take care of it.”


“I’ll get to it next week.”

“The bathroom is disgusting. Will you please clean it tomorrow?”

“I’ve got a lot of shit to do tomorrow. I have to write a blog.”


“Yes, dear.”

The next morning, after enjoying a cigarette with my breakfast whiskey, I checked out the bathroom. My wife was right. It was nasty, an epic eyesore, foul, miasmic and cruddy. It looked like a fraternity house bathroom after a toga party.

I had my work cut out for me.

Tackling a job of this magnitude requires careful planning, steely-eyed determination, and, most importantly, the right tools.

I spent an hour gathering equipment – vacuum cleaner, mop, sponges, paper towels, Comet Cleanser, bleach, battery acid, hammer and chisel, machete, a Black & Decker jig saw, safety glasses, gas mask, a pint of Old Crow – and then I put my shoulder to the wheel.

I worked steadily, but wisely, stopping often to hydrate and regulate my nicotine levels. After a few hours, I broke for lunch and took a short nap. When I woke up I went out to the garage to smoke a little weed, then went back to work.

Seven hours later, the job was done. I was proud of myself. The bathroom was immaculate. An alderman wouldn’t have minded taking a dump there.

Best of all, I had done the job without sustaining any major injuries. Other than a few cuts and scrapes, and aggravating an old war wound, the job went off without a hitch.

When I went upstairs, my wife asked, “Did you finish cleaning?”


“Took you long enough.”

“Did you want it done fast or done right?”

The lovely Mrs. Milo seemed doubtful. “I’m going to have a look,” she said.

I followed her downstairs and waited while she inspected the job.

“Well, what do you think?”

“You missed a few spots,” she replied.

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Letter From Milo: Bend Over and Grab Your Ankles

March 24th, 2014

Corporal punishment was an accepted practice in the Gary, Indiana school system. Misconduct was dealt with swiftly and painfully. The instrument of punishment was always a paddle, which was known as “the board of education.” Customarily, it was a heavy, two-foot-long piece of wood with holes drilled in it.

As explained to me by a member of the Slide Rule Club, the holes in the paddle decreased air resistance, which allowed it to achieve maximum forward momentum when it made contact with your sorry ass.

A few of the male teachers had reputations as being quick to punish students, but the worst disciplinarians were three of the brutes on the coaching staff. The three coaches, two of them cousins, who I’ll call Coach Howard, Coach Fine and Coach Howard, were the school’s go-to guys when it came to paddling boys. Teachers that were too timid to punish students on their own sent their miscreants to the coach’s office to be straightened out.

The high school I attended was a hotbed of delinquency, the classrooms packed with ruffians, thugs, hoodlums, sneaks, and greasers. It was a rare day when there weren’t at least half a dozen guys lined up at the coach’s office, waiting to go inside, bend over and grab their ankles.

“Oh, man, I hope I don’t get Coach Fine. The fucker swings that paddle like Ernie Banks.”

“I rather have him than that creepy Coach Howard. Swear to God, he acts like he gets a kick out of beating on somebody’s ass.”

I was a troublemaker in school, especially during my freshman year, disruptive in class, a wise ass. As a result of my boorish behavior, I spent a lot of time, that year, in the coach’s office.

“Oh, no, it’s you again. When are you going to learn your lesson?”

“Coach, it was a misunderstanding.”

“What kind of misunderstanding?”

“Mrs. Shimkus said to turn to page 84 of Silas Marner. I thought she said turn up my transistor radio.”

“Bend over and grab your ankles. You’re getting three.”

The first swat always hurt like hell. The worst thing about it, however, was that you knew two more were coming. The second hurt as badly as the first, but the knowledge that there was only one more to come made it easier to take. The final swat was the most painful, because your ass was stinging and sore from the first two blows, yet knowing that the ordeal was over made the pain bearable.

The only thing the coaches hated more than unruly teenage students, were teenage smokers. If a kid got caught smoking, or with a pack of cigarettes, or even a pack of matches, he’d be required to report to the coach’s office.

After school, one day, I was walking along 5th Avenue, headed for the Club, which was my favorite pool room. I was smoking a cigarette as I walked, probably a Winston, when a car pulled up to the curb next to me. When the driver cranked down the window, I saw that it was Coach Howard. He gave me a stern look and said, “You be at my office before classes start tomorrow.”

I was a senior in high school, nearly 18 years old at the time, and would be graduating in a few months. I hadn’t been swatted since I was a freshman, three years earlier.

In those three years, I had grown a bit, lived a little, and learned a few things. One of the things I learned is that people’s motivations for doing things aren’t always what they seem. Sometimes people take actions for no apparent reason and to no apparent purpose. Other times, they know exactly what they’re doing, why they’re doing it, and what they plan to get out of it.

More importantly, people are sometimes motivated by what others think of them.

Coach Howard was waiting for me when I arrived at the office the next morning. “I saw you smoking on the street yesterday,” he said. “You got anything to say for yourself?”

“Guilty as charged, Coach.”

“That’s an automatic five swats,” he said, as he rose from his chair and reached for the paddle. “Bend over and grab your ankles.”



“I said no. I consider grown men spanking boys to be sick behavior.”

“Watch what you’re saying, boy.”

“I can’t think of any normal people who make boys bend over in front of them while they slap their butts with chunks of wood. It’s what perverts do, in my opinion. Some people might enjoy this kind of thing, but I cannot, in good conscience, engage in such behavior.”

Coach Howard stared at me for a while, wondering what the hell I was talking about. Finally, he said, “Get the hell out of my office.”

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Benny Jay: Man of the House

March 18th, 2014

Editor’s Note: Benny Jay has disappeared. We believe he’s suffered a relapse and gone on another friend chicken bender, but won’t know for sure until we get the report from the private detectives. In the meantime, we are running one of his older blogs. Sorry for any inconvenience.


My wife’s the first to detect the odor.

“Benny, there’s this weird smell under the porch,” she tells me.

She tells me this while I’m on the couch reading the newspaper.

Then she says: “Check it out.”

You know, like there’s something I can do about it.

“Do I gotta?” I ask.


Aw shit, I mutter. From the couch I rise. To the porch I go. I sniff the air.

“I don’t smell anything,” I say.

“There’s a bad smell, I tell you….”

“No, there isn’t,” I say. “Now, stop bugging me about it.

And back to the couch I go, where my newspaper awaits.

My wife walks out the door. Two or three minutes of peacefulness follow. Then….

“Ewww, Benny — it’s a dead squirrel!”

Aw, shit!

“Stop being such a wuss,” I say.

“It’s disgusting,” she says.

“Pick it up and throw it away — man it up!”

“No, you man it up.”

“Why should I man it up?”

“Cause you’re the man of the house.”

I hate to say it, but she has a point.

Then I say. “Just leave it alone — eventually, it will decompose.”

Fast forward a day or two. I walk out of the house. I sniff the air. Smell something awful — like rotting meat.

“Hey,” I yell to my wife. “There’s a disgusting smell out there.”

“It’s that fucking squirrel,” she says. ”

“I thought you got rid of it,” I say.

“No, I didn’t get rid of it,” she says. “Why should I get rid of it?”

Next thing I know, she’s on the front porch, shovel in her hand.

“C’mon,” she says. “Let’s get this done.”

I approach the squirrel. The little fucker’s lying flat on its back, legs flattened against the ground.

“How did it die?” asks my wife.

You know, like I’m the coroner.

“I dunno,” I say. “Let’s do an autopsy.”

She hands me the shovel. I walk to the squirrel. It smells awful. There are flies buzzing around the carcass. The smell’s so disgusting, I close my nose with one hand and shovel up the squirrel with the other. Then I dump it into a plastic garbage bag.

Only, the squirrel hits the rim of the bag and falls on the ground with a thump.

“Ugh, disgusting,” says my wife. “Maggots.”

Clearly, this is a two-handed shoveling job. So….

Smell be damned, I scoop up the dead squirrel with the shovel, dump it in the bag, and hand the bag to my wife, who takes it out to the garbage.

It’s never easy being the man of the house.

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Letter From Milo: Otis and the AARC

March 17th, 2014

I was out on my front porch, enjoying a cigarette with my morning whiskey, when the postman came by and dropped off the mail. Most of it was the usual shit — bills, junk mail, a subpoena, a couple of magazines, and meds from my favorite off-shore pharmacy.

There was also a letter addressed to Otis, the rotten bastard of an alley cat who’s made my life a living hell for the past 13 years.

I was puzzled. To the best of my recollection, Otis had never received mail before. I wondered why anyone would send the dumbass a letter. I doubt the fucker even knows how to read.

When I told my wife, the lovely Mrs. Milo, about the letter, she asked, “Who sent it?”

“The return address says AARC in Washington, D.C.”

“Well, open it.”

When I opened the envelope, I saw that the name on the letterhead was “American Association of Retired Cats. “ There was a membership card, with Otis’ name on it, attached to the letter. There were also a lot of coupons in in the envelope. I was looking at one when my wife asked, “What’s that?”

“It’s a coupon for Petsmart. Otis can get a 20% discount on his next purchase of catnip when he presents his AARC card.”

Otis is growing older. The signs are obvious. He wakes up several times a night to urinate. He has liver spots on his paws. His hairline is receding. He’s losing interest in pussy. Years of catnip abuse have ruined his kidneys. He has a touch of emphysema. His teeth are in bad shape and he’s plagued by arthritis. And he still hasn’t recovered from the brutal beating he had taken from a feral tabby, more than a year ago.

That said, even though I know Otis is getting old, I had no idea he was close to retirement age, a senior citizen cat. In fact, I don’t know the cat’s exact age. Nobody knows.

When the mangy bastard followed my youngest daughter home, about 13 years ago, and weaseled his way into our household, my wife immediately took him to the vet. The vet’s best guess was that the cat was two or three years old, which would make him 15 or 16 now.

Letting the cat into the house was a huge mistake. He may have fooled my wife and daughters into believing he’d make a respectable house pet, but I know Otis for what he really is – a thuggish, mean-spirited, treacherous, and conniving alley cat.

Over the years, I did my best to get rid of him. I tried everything – stuffing him into the microwave, running him over with the lawn mower, digging a cat-sized Burmese tiger trap in my front yard, tossing him on the third rail at the Rockwell el stop, but nothing seemed to work. All of my efforts failed.

The closest I came to success was when I made a deal to sell him to my dear friend, Mr. Choi, who owns a very popular home-style Korean restaurant on the North Side. Due to on-going problems with the City’s health inspectors, Mr. Choi had to back out of the deal at the last minute.

When I discovered that Otis had become a member of AARC, I knew my troubles were almost over. His situation is not much different than when a person becomes a member of AARP. It means the end is near. The game is in the fourth quarter.

A healthy cat can live 20 or more years. But Otis is anything but healthy. He is a party animal, a self-destructive carouser, the feline equivalent of a heavy drinker and four-pack-a-day smoker. In my opinion, he’s lucky to have reached the age of 16. I’d be surprised if he lasts another six months.

Time is on my side. It won’t be long before I’m finally rid of the cat. It’s a waiting game and I’m a patient man.


Letter From Milo: Don’t Look Back

March 10th, 2014

An old friend from high school, who I’ll call Lenny, to spare him undue embarrassment, did well in life. He became a hot-shot attorney and made a lot of money. He drives nice cars, dresses well, eats at fine restaurants, takes expensive vacations, lives in a condo on Lake Shore Drive, and owns a cottage in New Buffalo.

But Lenny’s greatest pleasure, the one thing that most satisfies his soul, is tracking down girls he knew in high school and seducing them. Specifically, he goes after women who wouldn’t give him the time of day in high school, girls who completely ignored his pimply, awkward, and geeky young ass. So far, two cheerleaders and a homecoming queen are among his conquests.

Lenny and I talk on the phone every few months. Our conversations go something like this:

“Hey, Milo! Guess who I fucked last weekend.”

“I have no idea, but the unfortunate woman has my sympathies.”

“Do you remember Debbie Snyder? She was in Mrs. Shimkus’ algebra class with us.”


“She’s divorced now, lives in Indianapolis. We’ve been e-mailing back and forth for a couple of months. Last Saturday, I drove down there, took her out to dinner, and spent the night with her.”

“Wait a minute. You drove four hours, each way, to spend one night with a 65-year-old woman?”

“Yeah, and it was great, too. But I’ve got a question for you.”

“Go ahead.”

“Do you, by any chance, know how to contact Carla Gonzalez? I heard she lives in Cleveland.”

Some people get stuck in time warps. They find an era, a place, or a mind-set that makes them happy, and they stay there. If such times or places never existed, they make them up.

My friend, Lenny, got stuck in high school, but the school he envisions bears no resemblance to the one he actually attended. He is rewriting his personal history.

In his re-imagined high school life, Lenny is no longer a chubby, socially-inept loser, shunned by the girls, tormented by the jocks. Instead, he is the Big Man on Campus, envied by the guys, lusted after by the girls.

When Lenny is romancing a former classmate, I’m sure he doesn’t see himself in bed with a senior citizen, an AARP member, or a grandmother. What he sees is a nubile young woman, the girl of his dreams, someone who had once been unattainable. And now, finally, after all these years, he’s doing it to her.

I’m not the type to look back. I’ve done too many stupid things, and made too many mistakes, to make reflection worthwhile. Looking for one perfect moment in life and re-living it, over and over again, seems like an exercise in self-delusion.

Besides, there are not that many perfect moments in life. I’ve had a few, but I’d hate to try and relive them. I doubt my health could stand it.

Still, you’ve got to admire a guy like Lenny. He never gave up. He’s the classic high school rags-to-riches story. He started out as a nerdy, overweight loner, more comfortable with a slide rule than with other people, and ended up sleeping with the homecoming queen.

And it only took him 40 years.

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