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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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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