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Friday, April 10, 2026

April 10th, 2026

 Sleeping during a rainstorm is the best way to start a Friday.

Have a fantastic weekend.
I’ll be at Shanahans today for the last time. I will never find gusto or astonishment at 7353 West Madison Street ever again…
Add Shannys to a long list of places that hold fond memories and are gone.
Zum Deutschen Eck
Parthenon
Sabbatino’s
Schaller's Pump
Southport Lanes
Heaven on Seven
Gennaros
Chicago Brauhaus
Come Back Inn
Klas
Hickory Pit
Cozy Corner in Oak Park
Slicker Sam's
Gossage Grill
Mirabels
Gina's Italian Ice
McCuddy's
Sauer's
Binyon's
Wabash Inn
Roditys
Broker's Inn CBOT
Ronny's Steak House Loop
Bishop's Chili 18th/Damen
Trader Vic's Palmer House
Rosita's in Westchester
Agostinos
Wally's Red Hots
The Dumpling House
Jim's at Halsted and Maxwell
Rocky's Fish House/Navy Pier




Thursday, April 9, 2026

April 9th, 2026

 At my age, if they’re talking about me, it is none of my business. If you don’t like me, that’s fine, keep your distance.

If you yell at me, watch for the smirk. If a Prince song comes on, watch me dance. If Sinatra’s playing, I’ll sing it my way.
I’m going to take care of the Shepkids. Give my boss his money’s worth and spend time with the people who matter while I still can.
No more punting, I’m going for it on fourth down.
I don’t lean on empty hope anymore.
I lean on optimism and faith to carry me through.
Walk your walk Chalkheads and let people talk.
We got this…..




Wednesday, April 8, 2026

April 8th, 2026

 There is some sort of pile in all of our lives.

It doesn’t look like much at first glance. Maybe a few bad habits or a few stale names. A few negative thoughts we have been carrying around longer than we should.
Stuff that once mattered. Stuff that might have even saved us at one point.
But not anymore.
Now it just sits there taking up space blocking out the light and keeping anything new from taking hold.
We don’t get rid of it because it is familiar.
We don’t get rid of it because it is easy.
We don’t get rid of it because we don’t know what life looks like without it.
So we drag it along, dead wood.
Here is the honest truth…
…nothing grows in a pile of dead wood.
Not relationships.
Not discipline.
Not peace of mind.
I f you want something new, you don’t add more. You clear out the old and get rid of it to make room.
And yeah… burning it might cost you something.
Memories.
Comfort.
Excuses.
But holding onto it costs you much more.
So today, take a look at your pile and burn it.
I didn’t forget that yesterday was National Beer Day. It was also National Coffee Cake Day. I was tossed on which to pick, so I didn’t.
I love beer and coffee cake and if I’m tailgating and both are there….
Go Team!
Because that is the only time I have ever enjoyed beer and coffee cake together. A couple hours before kickoff sitting in the shadows of a football stadium.




Tuesday, April 7, 2026

April 7th, 2026

    A local in the Ten-Year pit turned to me and said a buddy of his was opening a new bar and restaurant in the neighborhood.

“Go over and ask for a job, I’ll put in a good word for you.”
I was an arb clerk on the trading floor, renting my first apartment in Oak Park, and a little extra money could help. The rest is history. The year was 1991.
It was the beginning of a love affair with what would become my happy place in the world, but still close to home.
I worked there for a while but felt more comfortable in front than behind the bar. In those early days, when youth still filled my heart, I would jump up on the bar and dance...
...and when the song ended, I would jump back down.
My ankles, knees, and hips cringe at the memory.
I threw legendary Christmas parties, epic Mardi Gras parties, and even had my dress rehearsal dinner at 7353 West Madison.
I met dear friends that I still have today. Friends I only knew for one night and characters who came and went with the last call.
There was a sad lady who reminded us of Blanche DuBois from A Streetcar Named Desire. She drank a cocktail called a Salty Dog. So she became the Salty Dog at the end of the bar.
There was the Bank Dick. A neighborhood kid who had suffered a brain injury as a child. He was outgoing, always ready with a riddle or a limerick for anyone who would listen. A short guy with dark glasses, dark curly hair... looked a little like Woody Allen.
We called him the Bank Dick because he would finish a conversation, walk to the back corner, and jot notes into a small notebook he pulled from his jacket pocket.
Years later, we found out he was writing things down so he wouldn’t forget who he met, where he was and what happened. The injury affected his memory, but you would never know it. He was always sharp as a tack and sober as a judge.
There was Mike, part owner, part bartender, part cook and full-time customer. Tall, lanky, a swimmer at the local Catholic high school and a Big Ten college. He had a thick walrus mustache that covered his mouth and held the foam from his beer.
One night he took a bet that he could drink a shot from the spillage in the muck bucket under the bar sink. The one where all the used glassware was dumped before being washed.
Melted ice, backwash, bruised fruit, drink stirrers, the last sips of everything, muddled together in a five-gallon bucket.
Mike slammed it.
That was the last time we saw Mike for several months.
He got sick, real sick. It became a bit of a legend that the bucket muck did him in.
The regulars became friends. Sometimes they became family. They had baptism showers, wedding showers and many fiftieth birthday parties.
The food had a Cajun-Creole flavor... famous for jambalaya, gumbo, and especially the voodoo pork chops. And they made a Hurricane just like Pat O’Brien’s down in the French Quarter.
Whenever I was sad, I went to the bar.
Whenever I was happy, I went to the bar.
It is the only place where my father, my mother, my closest friends, my first love, my cousins, my in-laws, their daughter and the children we made all broke bread with me.
It is the common thread of where I gathered all the people who thought I was special.
There had been rumors for years that the owner, now in his seventies, wanted to sell.
He sold it last month.
And this weekend will be the last time the Cajun and Creole neon lights shine on the facade at Shanahans.
I went from my mid-twenties… to dating… to celebrating milestones… to marriage… to fatherhood… through divorce… and into my late fifties knowing that if I needed a memory-induced boost, I could drive to the Cajun/Creole Irish Pub on Madison Street in Forest Park.
I always thought people would gather at Shanahans after my wake and funeral. That the people who made me happy would meet in my one happy place.
Instead, I will be there Friday night, celebrating my last supper at Shanahans.
A couple more hours.
One last bowl of gumbo.
One last plate of jambalaya.
One last pork chop smothered in Tim Shanahan’s voodoo hollandaise.
And a couple, two, tree Hurricanes to wash it down.
But I definitely won’t be dancing on the bar.
Farewell, old friend.
You were the one constant from the peak of my youth to the beginning of my senior years. Thank you for the shoulder to cry on. The palm to high-five in jubilation. The ear that listened to my triumphs and my tribulations and the place I could always call home.
The next time I go to Shanahans will be in heaven.
When we all gather again in Eternal Étouffée.....






Monday, April 6, 2026

April 6th, 2026

 You ever notice how nobody throws you a parade when you are doing the right thing?

No fireworks, no headline, no marching bands on State Street, and no guy from Channel Nine asking how it feels to be noble on a Monday morning.
You just get up, do what you are supposed to do, and most of the time nobody even nods.
That is conviction and conviction builds integrity.
It is the stuff you do when there is nothing in it for you. There isn't applause and there is no guarantee anybody’s even paying attention.
Now take those two guys on the Road to Emmaus.
Walking along, probably complaining like a couple of guys stuck on the Eisenhower at rush hour.
And there He is, right next to them.
They don’t see it. Not at first.
Because recognition doesn’t come easy. It shows up late.
After the work has been done. After the walking is over. After you have already decided who you are.
That is the part nobody likes.
People want recognition first. They want the headline before they have written the story.
Doesn’t work that way.
You live it first.
You believe it first.
You walk it out when nobody’s watching.
Then maybe you recognize what was right in front of you the whole time or maybe you don’t.
But either way…
...you still had to take the walk.



The Road to Emmaus comes from the Gospel of Luke (Luke 24:13–35).
After the crucifixion of Jesus Christ, two disciples are walking to the village of Emmaus, discouraged and confused. Jesus joins them on the road, but they don’t recognize Him.
As they walk, He explains how the Scriptures foretold His suffering and resurrection. Still, they don’t realize who He is.
It’s only later, when He breaks bread with them, that their eyes are opened and they recognize Him. Then He vanishes.
The point, plain and simple:
They were walking with Him the whole time they just couldn’t see it. This story is also an early sign on the importance of the Eucharist and it being the closest we get to Christ during our lives.

Saturday, April 4, 2026

April 4th, 2026

 Yesterday was a grand day as I celebrated Opening Day with a dear group of friends.

As we watched the ballgame, we chatted amongst ourselves. Both as a group and in smaller, individual conversations. We talked about work, retirement, family, health, and we laughed about all the memories that have piled up throughout our lives.
Then one of my buddies nonchalantly said that we are going to start losing guys from this group.
Morbid as it sounded during a gorgeous afternoon on the third base line at Comiskey, it was unfortunately the truth.
The statement was hard to handle and just as difficult to brush off.
To lighten the moment, I suggested we start a Deadpool. I would take the guy who pondered the idea and myself.
Then I suggested we not wallow in the conversation but rather enjoy the moment around us. It will be an instant memory tomorrow and a distant one in the years to come.
Someday we will gather and talk about the home opener in 2026 that fell on Good Friday and laugh about our Catholic guilt keeping us from eating a polish sausage.
Then, as we leave the wake, we will agree that Tom was right on that beautiful Friday afternoon in the fifth inning.
The lads we celebrated all our milestones in life with are vanishing from our lives.
What a morbid fucking thought on what I probably should have chalked about the shits and giggles we had instead.
But if one thing comes from that conversation in the April sunshine, it is this…
… I will love that group of men even more.
Give them hell Wild Turkeys, may we all be ghost runners in extra innings.








Friday, April 3, 2026

April 3rd, 2026

      I haven’t chalked all week.

Not out of respect for Holy Week and Passover, but because I’ve been sicker than a dog.
Sick enough to take Wednesday off. That alone should’ve told you something was wrong.
I went to the Doc in the Box to figure out what was dragging my big cheeks down. They rammed the swabs up my nose, disappeared, and came back fifteen minutes later. No strep and no China Flu.
So now they want more tests.
Fine, I trust this guy. This is the same drive-thru doctor who diagnosed Fritz with appendicitis. The man is batting a thousand in my book.
They take a picture of my lungs. Then instead of violating my nostrils again, they go straight for the mouth. If I had anything in my stomach, that guy would have worn it.
They come back again with more good news, it isn't pneumonia.
But now… I forgot to tell you that it was April Fool's Day.
The young doctor who skipped the razor and tied his man bun up in a net tells me I have RSV.
Now here is where I almost caught an attempted murder charge.
“Mr. Shepley, RSV is very common in people your age and can be serious for seniors.”

Look… I’ll admit it. It took effort to get out of the car. My chest was tight and my breathing wasn’t great. Yeah, I had the hunchback shuffle going and I could have used a cane. Sure, my scrotum was swinging halfway down my hip-hop thighs.
But how in the hell did I get lumped in with the King’s Court pinochle club over at Christ the King? Are they going to put me on the short bus with the wheelchair lift and drive me over to Little Sisters of the Poor retirement home?
I get up before everyone except the guy milking the cow.
I do fat cheek yoga.
I swing kettlebells.
I stand at my trading desk all day every day.
I chase 10,000 steps daily like it owes me money.
And this guy is telling me RSV is common for us kids born in the sixties?
Hey Class of '84!
Watch out for Respiratory Syncytial Virus!
It is common with old people like us!
That is kick one to the throat this week. Kick two comes today, Good Friday.
I’m heading to Sox Park for the home opener on a major Holy day in the Catholic Church.
Now let’s review the rules. Roman Catholics, 18 to 59: One full meal. Two smaller ones. No snacking. And if you are over 14, NO meat. Day of penance. Reflect on the Passion.
I copied that straight from my 1976 altar boy manual.
So now I’ve got a question....
How am I supposed to cheer for my beloved White Sox while my Savior is getting the snot kicked out of Him?
And more importantly…
Does His Father really think my faith is strong enough to withstand the smell of grilled onions floating through the Comiskey Park concourse?
Because I’ll tell you right now, that is a heavy lift. Not as heavy as a cross and crown of thorns, but it will test my faith.
Pope Leo never got back to me. Father Bobby from the Southside never returned my messages.
No dispensation.
No blessing for the sausage trifecta.
No clearance for nine Old Styles.
So let’s be honest... Who is really suffering here?
The skinny Jewish kid on Golgotha…
or the heavyset Catlick kid in Bridgeport?
What I have learned during my break from the Morning Chalkboard is this: I am a senior citizen with questionable lungs…
and an even more questionable level of discipline and faith.
At least if I end up in Hell, the heat will clear out my chest. And who knows, I might finally lose the fifty pounds.
Wish me luck, Chalkheads.
Because even though I still feel like ass…
I am still heading to the Southside to find a little gusto and astonishment anyway.




Monday, March 30, 2026

March 30th, 2026

 Today is the 60th birthday of the first woman I ever fell in love with as an adult.

We loved each other… and then it ended.
That is when my Oldman gave me something that stuck…
…very few people in this world think you’re special. When you find those people, you keep them around.
That is the whole game right there. You need to figure out who actually thinks you are special.
Sure… parents, grandparents, siblings, cousins, they count, but they have to because they are family.
But friends come and go. Lovers come and go. Mentors, teachers, neighbors… people pass through your life like traffic on Harlem Avenue.
But which ones really saw you?
Which ones thought highly of you?
When you figure that out, those are your people. Those are the ones you hold onto.
It was a theory my dad lived by, and it is one I carry forward.
There was a stretch where my 60-year-old friend and I weren’t close, but I stayed after it and over time, we built something again.
She is someone special to me and I believe that feeling runs both ways.
She has seen it all, my marriage, the kids and the divorce. She is so woven into my life, she’s George’s godmother.
The Oldman was right. There aren’t many people left who think I’m all that special. Many have passed on.
Who is left?
A few cousins. A couple of aunts and uncles. Maybe a handful of friends. Maybe a colleague or two. Even my mother-in-law still likes me… which says something, considering her daughter does not.
And sure, a few of the women from both chapters of my bachelorhood still think I’m alright.
That’s the Don Shepley theory.
He took it one step further: “If a woman has seen you naked, you sure as hell better not burn that bridge, son.”
There is wisdom in that, whether you like it or not.
Now it’s my job to teach the Shepkids. How to meet people. How to know the difference between a friend and an acquaintance…
…And most importantly, how to recognize and hold onto the Someone Special group.
Because our time together is short and this isn’t all that complicated.
You keep those people in your life until one of you is gone. Then you deal with the fact that there is one less person in this world who thinks you are special.
I am lucky that I still have one of mine.
Someone who thinks I’m special, and I feel the same way about her.
Happy Birthday, Weavie.
Our love changed shape, but we never lost each other. And we won’t, at least not until one of us finds eternal peace.
You are the definition of Someone Special Day. The Oldman loved you. He told me to work my ass off to keep you close.
If you ever think about the days when I was an assclown, just remember…
…God gave me a redheaded daughter to settle that score.
The Someone Special Theory. Reach out today to those who think you are someone special and let them know.




March 29th, 2026

 It is Palm Sunday.

A day when we commemorate Jesus Christ’s triumphant entry into Jerusalem and the beginning of Holy Week. The crowds waved palm branches and welcomed Him as King, not knowing what the week would bring.
It is going to be a big week for the skinny, long-haired Jewish kid.
As a Christian, it is a week to take a hard look at my faith. Not the version from years ago, but the one I’ve carried, or maybe drifted from, over the last fifty years. I need to figure out the role that faith will play going into my last twenty or thirty years.
Because without a grip on faith, everything else starts to give. Faith is what steadies us when life keeps throwing punches. I can’t overthink the faith part this week. I can’t figure it out in seven days, but live it with every morning get up.
This week starts in March and ends in April.
Thursday is Opening Day for the White Sox. I’ll be with a good group of friends. It’s also Holy Thursday, the night Jesus sat down with His friends for the Last Supper.
He gathered with His people and I’ll be gathering with mine. Same idea, but they go to a seder and we are going to a ballgame.
I gave up Chicago food for my Sixty Days of Cecilia, but I might have to call her on the heaven phone and ask permission for a hot dog and a Maxwell Street sausage.
We’ll see how that conversation goes.
It is the last Sunday of March. Get outside and watch the sunrise. Go find some gusto and astonishment.




Saturday, March 28, 2026

March 28th, 2026

 I don’t have much to chalk about this morning.

Here we are finishing up March already. Spring has begun with the usual bipolar symptoms.
Baseball started last week and in typical fashion, both Chicago teams crapped the bed on opening day.
As we switch into April, Holy Week and Passover arrive. A time where we strengthen our relationship with our faith, family and friends. It is where we embrace the traditions of our Judeo-Christian beliefs.
Either blood over the door or blood dripping down the cross, we must stand together and find peace in this world of hate.
That’s what you get with the Morning Chalkboard.
Friday I’m chalking about boobs and Saturday I’m pulling spiritual stuff out.
Let’s finish March with fulfillment and begin April on the path to astonishment and gusto.
And none of that mickey mouse bullshit on April 1st. I’m not in the mood for the ketchup on hotdog memes you Chalkheads post to piss me off.
The quote today is more for show. When the Shepley brothers wake up and see it, hopefully another seed is planted.
The grabber section is another Latin lesson. It means to make haste slowly. A reminder to move efficiently but avoid careless mistakes.
Like my Oldman always said, “when you make mistakes, make sure they don’t cost me a ton of money son…..”
I put a smile on the sun, go smile back at it!




March 27th, 2026

 I went with Sarte the other day, now I’m going with Camus. You Chalkheads might think I’m becoming an existentialist!

The grabber section is pretty clear.
Those boobs we once longed to grab in 7th grade belong to the girls that we grew up with. Let’s make sure the women that we love are healthy and happy as we settle into these later years.
I might be more of an ass man, but the breast cannot be ignored. I know that sooner or later Hazel will read my Chalkboards. My mother-in-law is a Chalkhead and she is reading right now.
From our daughters to the mommies to the women in the graduating classes before us. Their mental health and physical health are important to keep an eye on.
Now I know that it might sound easy for a guy who sleeps alone and doesn’t have to deal with a partner experiencing menopause, but I still have a shit ton of JumboLove that I love and need to protect.
So, Tits up to everyone!
From the women who place them into a bra to the men that caress them.
We are in this together…. Tits Up!
... And Hazel… yes, dad will always be embarrassing!




March 26th, 2026

 It’s Opening Day, 2026. The Southsiders are up in Milwaukee, and the Cubbies are home on the North Side.

Let’s pray that smile on the sun sticks around into the late innings this afternoon.
The quote this morning comes from Pete Rose, and I get his point, but I’ve sat at both Wrigley and Comiskey during a winter wonderland.
I’m not too excited about my ball club this summer. Truth is, last year was the first time I didn’t go to a Sox game since the early ’70s. That says something about the product they put on the field.
A lot of people that I once knew never saw the Sox win the World Series. I was lucky that they gave me one in my lifetime. That’s enough to keep the door cracked every spring.
These days, I am more excited about Pope Leo. We both say the same prayers every morning and we both cheer “White Sox” towards the end of the seventh-inning stretch. Old habits don’t die, they just settle in and make great memories.
If nothing else, baseball gets us to football season. That, and grilled onions on a hot dog, are about all I need from the White Sox…
…well, that and a couple cold beers.
Gusto, astonishment, and grand slams.
Let’s play two.




Wednesday, March 25, 2026

March 25th, 2026

 Everywhere I go, everything I do, I do alone.

I go to dinner alone.
I go to the pub alone.
I go to mass alone.
I go to bed alone.
I sit on my balcony alone.
I run my errands alone.
And the thing is… when I do all of that alone, I’m never lonely.
I was an only child. I’ve always been alone. Even on a trading floor with thousands of people, I’d leave and go off somewhere on my own after the closing bell.
I’ve been to more baseball games by myself than with friends or a date. Nothing better than sitting at Sox Park with a scorecard, a sack of peanuts, and a beer vendor who knows his job.
Thirty some years ago, I was sitting down the first base line at Comiskey on a summer night. A couple buddies of mine were sitting in Mayor Daley’s seats with their family.
“I think I see Jumbo sitting by himself.”
“Let’s go get him.”
I went from shooting the shit with strangers to sitting in those seats near the Sox dugout making memories with the Grace family. To this day, they still give me grief about how they “saved the lonely guy.”
They had it wrong then… and most people still do.
Alone isn’t lonely.
I still live like that latchkey kid from the late ’70s. I take care of myself. I don’t ask for help. I just do it.
There are perks.
I can leave the peanut butter out on the counter.
I don’t have to put the toilet seat down.
I can take a nap when I want.
Wake up at the crack of dawn.
I can make coffee or make a mimosa, it doesn’t matter.
The older the Shepkids get, the less time they want to be around a fossil from the last century. That’s alright, because that is the way it goes.
I have three knuckleheads that love me. I’ve got a job I love going to. I have a good place that I call home. The ladies at the bakery and the hotdog stand know my order by heart. My bartender welcomes me with a big hello when I walk into the pub and all my neighbors wave to me when they walk by the balcony.
Next August, when I turn sixty, I’m taking myself to Gene & Georgetti’s. Big steak, gin martini and a nice bottle of wine. Table for one, no need to make reservations.
I chalked this Sartre quote and it stuck with me. It fits where I am right now in life.
A divorced dad who gets up, makes his bed, goes to work, comes home, goes to bed… and does it again the next day.
Keep good company, Chalkheads, even if that company is yourself.