Letter From Milo: A Shameful Episode

September 4th, 2019

The high school I attended was blessed with an abundance of beautiful girls. Everywhere you looked there were long-legged teenage beauties, with angelic faces, fine butts and perky young tits. It was a paradise for an aspiring pussy magnet (see appropriately titled post). I spent most of my high school years walking around with half a hard-on.

The best looking girls in the school were the Anderson sisters. They were every young man’s fantasy, beautiful, poised and shapely. I’m sure they were responsible for the vast majority of soiled sheets in my school district. I know that my laundry bills skyrocketed.

Ordinarily I wouldn’t have hesitated to approach one of the Anderson sisters, maybe invite one of them to see a movie or go to a school dance, then, afterward, hope to get extremely lucky. But, to my eternal regret, I never did ask one of them for a date. In essence, I chickened out.

You see, there was a problem with the Anderson sisters. They were African-American and I was not. And in Gary, Indiana, the racial divide was a wide one.

I was a freshman in 1964, when my high school was integrated. To say the least, it did not go smoothly at first. There were fist fights nearly every day, tough blue collar black kids and tough blue collar white kids beating the shit out of each other to prove, well, who knows what they were trying to prove? There were police cars parked by the school every day to keep the violence from getting out of hand. Not that it mattered. When young men want to fight, they generally find a way.

In time, however, things settled down. After school brawls became rare as the black kids and white kids began to accept each other. Tentative friendships were formed that often turned into genuine friendships. Black and white jocks began hanging out together. Black and white misfits began drinking cheap beer and smoking Lucky Strikes together. And black and white nerds probably got together to practice their slide rule chops.

But the one gap that was never bridged was interracial dating. It was too much to ask in the mid 1960s. I don’t recall ever seeing a black and white couple walking the halls of my school and holding hands. I don’t remember ever seeing a teenaged black and white couple out on a date. It just wasn’t done.

Now, you’d think that a legendary pussy magnet like me would be the one to break the interracial dating taboo, especially with a prize like the Anderson sisters at stake. I mean, let’s face facts, beauty is beauty, no matter what kind of package it comes in.

But no, the great Milo, in his teenage years, didn’t have the balls to do the right thing — the right thing being taking my best shot at the best looking girls in town. I had let down pussy magnets everywhere.

Would Errol Flynn have hesitated? Would the immortal Porfirio Rubirosa have given it a second thought? Would a beautiful woman’s skin color have mattered to Warren Beatty? No! But young Milo couldn’t come up with the goods when the occasion called for greatness.

It is a failure that haunts me to this very day.

Times have changed. We have all moved on, even the Anderson sisters. One of them, with a slight name change, became a well known entertainer. I don’t know what happened to the other sister, but I assume she did well in life, too.

As for me, I became a famous and highly paid blogger here at The Third City. I spend my days thinking deep thoughts and my nights wandering the streets of Chicago. And whenever I see an interracial couple, and I’m glad to say I see them often, I curse myself for being the worst sort of idiot, a disgrace to pussy magnets all over the world.

How did I ever let the Anderson sisters slip through my hands?

Pussy magnet, my ass.

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Letter From Milo: Great Thoughts

August 28th, 2019

Once again, I’m up against a deadline and don’t have anything to write about. So, I’m going to fall back on the lazy columnist’s trick of posting letters from readers. I know I’ve been doing this a lot lately, but I’m going to plead extenuating circumstances. I’m not sure if the abuse of alcohol and drugs, plus an epic sex life, qualifies as extenuating circumstances, but that’s my excuse and I’m sticking to it. Anyway, here are a few letters from The Third City’s loyal, discerning and genteel readers, followed by my snappy replies.


Motherfucker, where’s my money!

Snappy reply:

Oh, shit! Is this Elaine from Elmhurst? Didn’t you get my last email? I told you I’m not sending you any money until the DNA results are confirmed. How did you find me, anyway? Man, I hate Google.


Me and the guys here at Burr Oak Cemetery are big fans of your blogging. We thought that the stuff about your recent medical problems was some of your best writing. We especially enjoyed the one you wrote about having your teeth pulled before your heart surgery. It occurred to me that you might be in the market for a dental plate. Here at Burr Oak we have a wide variety of nearly new and gently used dental plates for sale. And they cost a mere fraction of what a brand new dental plate would cost. If you’re interested, call Burr Oak Cemetery and ask for Lennie. We look forward to hearing from you.

Snappy reply:

Damn! I wish you would have contacted me a little earlier. I’ve already been fitted for a dental plate at the Triple A College of Dental Prosthetics & Drywall Academy in Gary, Indiana. But I will mention your offer to several of my toothless friends, who, no doubt, will be deeply appreciative of your kind offer.


Hey, bro, this is your brother-in-law, Bill. Your sister has been making my life miserable lately. She’s been accusing me of all sorts of terrible things, including being a drunkard. A couple of days ago she hit me in the head with a frying pan. Good thing I was drunk or it would have hurt like hell. Then, yesterday morning, she bought a subscription to Guns and Ammo and, later that day, she joined Jenny Craig. Plus, I think she’s been sneaking around with the assistant golf pro at the country club. I’m getting a little nervous. What should I do?

Snappy reply:

Dumbass, I warned you when you married her that you were getting in way over your head. My sister is a mean, vengeful, violent, high maintenance bitch. Matter of fact, when I was a young man, still living at home with my family, I had to go to Vietnam just to get away from her and find some piece and quiet. The best advice I can give you is to start defending yourself. Now, I am totally against the abuse of women. The only woman I ever hit was 4th Ward Alice, when we had that savage street fight on Lincoln Avenue back in the ‘70s. I would have whipped her, too if she hadn’t sprayed me with mace and kicked me in the nuts. As I mentioned, I’m against hitting women, but in my sister’s case I might make an exception.


I always thought that you were Gary, Indiana’s greatest writer. Now I’m hearing that someone named Monroe Anderson is being touted for that title. There’s been quite a debate on Facebook as to who is actually Gary’s finest scribe. Can you straighten this out for me? I’m confused.

Snappy reply:

Let me set the record straight. Monroe Anderson is a barely literate, no-talent hack. As a writer, he is in the same league as Benny Jay and Big Mike, which is to say they are all bush leaguers. I doubt Monroe is even from Gary. He probably grew up in Muncie or Fort Wayne, or some backwater in southern Indiana. He just says he’s from Gary to improve his social standing. Granted, being Gary’s greatest writer is not the most coveted literary accolade. It’s sort of like being the handsomest of the Three Stooges (although Shemp is, in my opinion, a fine specimen of manhood). Still, the title is all I’ve got and I’m not giving it up without a fight, no matter what they say on Facebook. By the way, what is Facebook?

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Letter From Milo: A Broken Man

August 5th, 2019

It’s been bitterly cold in Chicago the last couple of weeks. Temperatures have rarely gotten above 10 degrees and the wind chill has been below zero for days at a time.

The other day I had to run some errands which required me to spend a considerable amount of time outdoors, waiting for buses and el trains. Being a man of some experience, and a devoted watcher of the Weather Channel, I know that the secret to staying warm in inclement weather is to wear layers of clothing.

When the weather turns Canadian on me, I pile it on – shirts, sweaters, corduroys, two pair of socks, a down vest, a thick scarf, insulated gloves, and over that I put on a heavy parka. In the words of the great Howlin’ Wolf, “I dress for comfort, baby, I don’t dress for speed.”

Living in the Midwest most of my life, I have discovered that the most important component of cold weather layering, the essential element in keeping warm in Chicago in January, is a good pair of long underwear. Yes, sir, you can’t beat lumberjack lingerie for taking the bite out of winter.

Anyway, that morning, as I was preparing to go out and deal with the elements, I couldn’t find my long underwear. I spent a few minutes vainly searching for them, then asked the lovely Mrs. Milo, “Honey, have you seen my long underwear?”

“I threw them out.”

“You did WHAT?”

“I threw them out.”

“Jesus, why? They were the only pair I had.”

“To be honest about it, they were just nasty.”

“What do you mean by that?”

“Well, they were ripped and torn and they had stains all over them.”

“Stains? What kind of stains?”

“The usual kind. Let’s just say they were the color of earth tones.”

“Damn it! I could have bleached those stains out.”

“I doubt you could have gotten rid of the stains with battery acid. Besides, you’ve had that particular pair of long underwear for at least 25 years. Just go out and buy new ones.”

I would have continued the dialogue, but I could see that it would eventually deteriorate into our usual heated discussion of each other’s faults and shortcomings. And, brother, that’s an argument I have yet to win. So, grumbling and muttering vague threats, I hopped into the car and drove to the Target store on Peterson.

Except for buying groceries, alcohol, tobacco and drugs, I don’t care for shopping. It’s poor sport, in my opinion. But I don’t mind Target too much. It’s what I imagine all stores would have looked like if the Soviets had won the Cold War. Unfortunately, this particular Target was out of long underwear. Puzzled, I stopped a store employee and asked, “How can you be out of long underwear in the middle of winter in Chicago.” The employee gave me a blank stare and went about his business. I figured English wasn’t his preferred language.

I called Mrs. Milo to complain, but she brushed me off, saying, “Just go to the Target on Elston.”

Unbelievably, the Target on Elston was out of long underwear, too. Now I was getting pissed. I didn’t even bother asking any of the employees about the underwear situation. I just got back in the car and called Mrs. Milo. I was just starting to get into a good rhythm of bitching and complaining when she cut me off. “As long as you’re on Elston, drive north to the Kmart,” she said, then hung up on me.

It wasn’t my day. The Kmart didn’t have any long underwear either. Now, I was steaming. “What the fuck is wrong with these people,” I said aloud, while listening to a CD of Black Joe Louis and the Honeybears. “Don’t they understand that long underwear are a necessity of life in certain parts of the world.”

I was driving aimlessly, feeling sorry for myself, thinking about picking up a short dog of Jack Daniels (another good way to stay warm in winter) and wondering what the world was coming to, when I drove past the Sears store on Lawrence. Aha, I thought, if anyplace on earth had long underwear, it would be Sears. I parked the car, dealt with Mayor Daley’s farce of a parking meter system, and rushed inside the big store.

Oh yeah, they had long underwear, except they cost 32 fucking dollars. The description on the package said that the underwear were made of two ply materials, one being a specially formulated synthetic that wicks away perspiration and the other being fine Marino wool that traps heat and keeps you warm even in subarctic conditions.

I’ll be damned if I’ll pay 32 dollars for a pair of long underwear. I don’t care if they are gold lame and made by Nudie, Elvis’ favorite tailor. Those cocksuckers at Sears can take their 32 dollar long underwear and stick them up their collective asses. I ought to report them to the Better Business Bureau. No wonder Sears is on the verge of going under. Serves the bastards right.

Of course, it was all sour grapes and empty threats on my part. As much as I complained, the sad reality was that I no longer owned a pair of long underwear. I would have to live with the consequences. And, in Chicago, those consequences could be brutal, if not fatal. The future looked grim.

When I left Sears I was a broken man.

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Letter From Milo: Loser City

July 28th, 2019

Due to the fiduciary lawlessness of Mitt Popovich, my sleazy fucking brother-in-law, The Third City Blog site has fallen on hard times.

That lousy mother fucker was the accountant of this scabby barely literate outfit. He claimed to have a degree from an esteemed online university, but the truth is we only hired him because my wife made me.

Now he’s run off to Argentina with our corporate assets, including $33.14 from petty cash.

The sad truth is that The Third City is broke. My last two paychecks have bounced. Yesterday, someone posted an eviction notice on the door of our Michigan Avenue corporate office. Our fleet of company cars has been repossessed. The company tab at the neighborhood bar has been cut off. The local whorehouse won’t take our checks anymore. And, worst of all, my drug dealer won’t return my phone calls.

I never thought it would come to this. When I left my last job, as Ethics Professor at the Moody Bible Institute, to join The Third City, I thought I was set for life.

After all, Big Arnie Raven, the Barn Boss of this flatulent outfit, had assured me that The Third City was one of the most popular and respected blog sites in the world, averaging close to a million readers a week. He told me that the site was on the short lists of both the Nobel and Pulitzer Prize committees, in several different categories, including news, sports and porn.

“Stick with The Third City, kid,” Big Arnie said, when I was hired. “The sky’s the limit.”

Well, the sky has fallen in on us. The Third City is in dire straits. Sadly, this may be the last blog we ever post.

But, I’m not a quitter. I refuse to let The Third City go under. This blog site is too important to the American people. In the words of some political dumbass, The Third City is “too big to fail.”

That’s why I’ve decided to hold a fund raiser. Yes, if NPR, Jerry Lewis and the Kiwanis can hold fund raisers, why can’t The Third City? We are every bit as deserving of feasting on the public tit as the above named organizations.

I have been working hard to keep this site afloat. I’ve been in contact with the new owners of the Chicago Cubs about using Wrigley Field as the venue for a fund raising benefit. My good friends, U2, the Rolling Stones and Bob Dylan have agreed to appear. Prince Charles is considering acting as emcee. Steven Spielberg has offered to create a 60 second TV spot to publicize the event. Monica Lewinsky has offered her services, in a capacity yet to be determined.

Despite the big name talent that has offered to help, it’s going to be you, our faithful readers who will make the difference. It is your contributions that will help keep The Third City a beacon of civilized discourse in a world of idiotic chatter.

That’s why I’m asking each and every one of you to reach into your wallets and purses, pull out a 20 dollar bill, place it in an envelope and mail it to me. I would appreciate it if you didn’t mention this to Big Arnie or Benny Jay. I want to, ah, surprise them.

I’m counting on you good folks out there to come to Third City’s rescue in this time of need. Just put that 20 dollar bill in a plain white envelope and address it to Milo Samardzija at 262…

HOLD IT! This is Mrs. Milo. I was just passing by Milo’s desk, saw what he was writing and chased him away from the computer with a broomstick. All he’s doing is trying to scam people out of money. Anybody that sends him money is a bigger idiot that he is. As for that crap about company cars, I doubt if Big Arnie, Benny Jay, Milo or that creepy Jon Randolph have enough brains between them to pass a driver’s license test. And the only corporate office they have is the corner coffee shop. Jeez, what a bunch of losers.

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Letter From Milo: China Or Canada

July 22nd, 2019

You can imagine my absolute shock when, just the other day, I learned that there were gay people living in China. I had no idea. I thought the only gay people in the world lived in the lower 48 states, with a few owning condo timeshares in some of the ritzier neighborhoods of Paris and London.

The Chinese are pretty tough on their gay population. Just the other day I read that the police broke up a parade that was to celebrate the coronation of Mr. Gay China. It must have been pretty tough picking one guy out of a population of a billion and a half people to represent gay Chinese, especially when, just a few years ago the Chinese government claimed that there were no gay Chinese at all.

The Iranian government also claims there are no gay people in their country. That must be the reason that Iran has terrible food, ugly architecture, no fashion sense, shitty haircuts, and no decent boutiques or antique shops.

I consider myself an extremely intelligent man, but there is one thing about gay people that confuses me. Where did they come from? If I remember correctly, there were no gay people at all in the USA until the early 1970s. They just appeared one day and made themselves at home. I was determined to find out where all the gay people came from, so I called my friend Benny Jay, who’s smart as a whip and asked him.

“Hey, Benny, have you noticed that there are an awful lot of gay people around?”

“Now that you mention it, I have seen a lot of them recently.”

“Well, where the fuck did they all come from?”


“Canada? Are you sure?”

“Positive. It was all part of that NAFTA deal.”

“Makes sense to me. By the way, do you know anything about this Mr. Gay China?”

“Guy China? Yeah, he’s on my bowling team.”

“No, no. Mr. Gay China. He’s this dude that supposed to be the epitome of Chinese gayness. They were going to have a parade to honor him but the Chinese police broke it up. They broke a few heads, too.”

“They must not have had a parade permit.”

Someone once said that the quality of a civilization can be judged by the way it treats its elderly. A better measuring stick, in my opinion, would be judging a civilization by the way it treats its minorities.

So, what’s the problem with gay people? Why do countries as varied as China, Iran, and, yes, the good ol’ USA, discriminate against gays. As far as I know, gay people do not commit terrorist acts. They rarely agitate for separatist states. Their hygiene standards are above average. They throw great parties. And if they move into your neighborhood that usually means your property values are going up. Other than an aggravating fondness for Broadway show tunes, they are generally good citizens.

I was still confused about the origins of gay people after I got off the phone with Benny Jay. So, I thought I’d call Big Mike, the Barn Boss of this scabby, low-life outfit. Big Mike knows everything. The man’s a walking encyclopedia, an oasis of wisdom in a desert of ignorance. He knows more shit that Professor Irwin Corey.

“Hey, Big Mike, it’s me, Milo.”

“Make it quick, asshole, I ain’t got all day. I’ve got a blog to run.”

“Ok, no problem. Have you noticed that there are a lot of gay people around?

“So what.”

“Well, I was talking to Benny Jay and he said they all came from Canada, part of that NAFTA deal.”

“Benny Jay’s an idiot.”

“I thought so, because I know a gay guy and he’s from Ireland.”

“You know what, Milo?”


“You’re an idiot, too.”

“Good talking to you.”

“Always a pleasure.”

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Letter From Milo: Living To Learn

July 16th, 2019

You’d think that someone who had heart surgery a few months ago would know better. You’d think that the person would have learned a lesson. You would suppose that someone who came this close to riding shotgun with the Angel in the Sharkskin Nightgown, would consider changing his wicked ways.

Well, I had open heart surgery recently and the only change in me is that my body has a few more scars to show off at the beach.

Against all common sense, against all medical advice, despite the anguished pleas of my wife and children, Ol’ Milo is at it again. Yes, folks, I’m drinking, eating red meat, sneaking the occasional cigarette, toking on the occasional joint and, once again, enjoying impure thoughts. Yes, sir, the Bum Gene (see one of my earlier posts) is in full roar.

Now, the obvious question is: How fucking stupid does a man have to be to continue a lifestyle that nearly killed him?

The obvious answer is: Very, very fucking stupid.

A short while after coming home from the hospital, my good friend, I’ll call him Bruce Diksas to spare him undue embarrassment, came by to visit. He brought along a few bottles of wine, a joint and a pack of Camels.

“You look pretty good,” Bruce said, uncorking one of the bottles. “Got some color in your face.”

“Yeah, I feel pretty good,” I replied, though I was still sore from the surgery where they had cracked me open like a lobster tail, then sewed me up like a hog being prepped for the barbeque spit. “Should be as good as new in a couple of days,” I added, lying.

“Here, have a drink. You’ll feel even better.”

“Good idea.”

As we sat at the kitchen table talking about the White Sox, the economy, pussy, the criminal incompetence of the Bush Regime, and Bruce’s upcoming trip the Bali, it occurred to me that just a few years ago Bruce had undergone some pretty serious surgery himself. I won’t go into details, but he came through it with his flag waving high.

It also occurred to me that many of our friends are suffering health problems. Granted, most of my friends have lived rather checkered lives, overdoing just about everything there is to overdo. But the undeniable fact is that they are all aging baby boomers, living at the tail end of the great post-war bubble . If our lives were basketball games, we would be entering the fourth quarter. Although there is always the chance of overtime, the sad truth is that you can’t count on it. I’ve had good friends die in their teens, 20s, 30s, 40s, 50s, and 60s. In one case a good friend died at the biblical age of 101.

They’ve died in all sorts of ways — car accidents, gunshot wounds, explosions, diseases, drug overdoses, jealousy, broken hearts, suicides and poor judgement. The common thread running through all these deaths is that, except for suicide, most people don’t have a say in the time and manner of their passing. It’s a lottery where the main prize is oblivion.

So, I suppose living into your 60s is an accomplishment of sorts. Although it’s a piss poor accomplishment, at best.

As Bruce and I started on the second bottle of wine, toked on the joint and lit up Camels, we smiled at each other, both of us aware of the game clock but happy to still be in the game and able to partake of some of our favorite vices. We clinked glasses and made a toast.

“To your health,” Bruce said.

“And yours, pal.”

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Letter From Milo: The Bump On Uncle Rudy’s Head

July 9th, 2019

Here are the last few pages of the 1st chapter of “The Aristocrat House,” in which Uncle Rudy learns one of life’s great lessons (see the last sentence).

The Aristocrat House

The bump on the head seemed to calm Uncle Rudy down. He sat up and looked around curiously, blinking his eyes, as if he had just awakened and was confused about his whereabouts. His chafed, swollen and bleeding face had a placid expression that slowly turned to a look of great sadness. Shaking his head and sighing deeply, he rose unsteadily to his feet and stumbled into the kitchen.

I followed him into the kitchen, just in case he attacked Vivian again. I didn’t know how I could stop him, or even if I could stop him, but I knew I couldn’t let him do anything more stupid than he had already done.

Uncle Rudy ignored Vivian, however, and went directly to the sink, where he turned on the tap and began splashing water on his abused face. After gingerly patting his face dry with a paper towel and lighting a cigarette, he turned to Vivian and said, “Viv, baby, we can work through this. It was just a little misunderstanding.”

Still seated on the floor and crying, Vivian blubbered, “Get out! Just get out!”

Trying to compose his battered face into a smile, Uncle Rudy replied, “Come on, honey, be reasonable. Every love affair has its rough spots.”

Vivian looked up and laughed bitterly. “Are you crazy! Get out before I call the cops.”

“Baby, baby, there’s no reason to…”

“I mean it! I want you out of here.”

Uncle Rudy tried to turn on the charm. “Sweetheart, you mean the world to me. What about all those great…”

“If you’re not out of here in 10 minutes, I’m calling the cops.”

“Ok, ok,” Uncle Rudy said, holding out his hands in supplication. “If that’s the way you want it.”

“10 minutes or I’ll have you arrested for stealing from me,” she said, angrily. “And take that pimply brat with you,” she added, unnecessarily, I thought.

20 minutes later we were driving away from Vivian’s, all of our belongings stuffed into the trunk or piled on the back seat. Uncle Rudy had pinched a couple of whiskey bottles before we left and had one propped between his legs, sipping from it as he drove.

“I can’t believe that one-legged cunt had the nerve to throw me out,” he commented, morosely. “And just when I was getting close to her money, too.”

“What makes you think she had any money?” I asked. I wouldn’t have guessed that Vivian had any real money. She dressed plainly, lived in a small apartment and drove a car that was three or four years old. If she had any substantial money, she hid it well. It seemed to me that she was just a lonely woman, desperate for company, who had run into some bad breaks, one of them being Uncle Rudy.

“Think about it,” Uncle Rudy continued. “She must have gotten some compensation for that leg. They’ve got laws in this country. You lose and arm or a leg on the job, they’ve got to pay you for it. I bet she was sitting on 10 or 15 thousand dollars.” Wistfully, he added, “You know what I could do with that kind of money?”

He drove a while in sullen silence, muttering and drinking, no doubt thinking about the fortune that had just slipped through his fingers. After working his way through a third of the whiskey bottle, he seemed to snap out of his self-pitying funk.

“It just goes to show you,” he said, ruefully, his words beginning to slur. “A woman doesn’t need two legs to walk all over a man.”

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