May 26th, 2026

   For the last two and a half years or so, I have been spending time at Bronswood Cemetery. It has become part of my routine to stop by for a visit.

That probably sounds strange to some people. Most folks think cemeteries are only for burials, final farewells and flowers. Places to visit out of obligation once or twice a year before hurrying back to the noise of everyday living.

Bronswood has become something different for me.

My father-in-law, PopPop Bergmann, is buried there. I like stopping by with a cigar, a couple shots of bourbon from my flask and whatever thoughts are rattling around in my head that week.

Sometimes I talk to him about the Shepkid. Sometimes I talk about work. Sometimes I talk to him about his daughter. Sometimes I talk about God. Sometimes I just sit there quietly and let the wind and the trees do most of the talking.

Not far from Mr. Bergmann rests Stan Mikita. If you grew up a Blackhawks fan in Chicago, you know exactly who Stan the Man was. One of the greats. A legend resting quietly just a grave away from regular people who loved each other and fought with each other. People who struggled and carried on just like the rest of us.

Bronswood itself feels alive in a strange and peaceful way. The cemetery rolls gently across hills lined with enormous old trees that have probably watched generations come and go. Some headstones date back to the 1800s, weathered and softened by time, while others bear dates from the 2020s. Still carrying that fresh grief of families learning how to move forward without someone they loved. Walking through reminds me that grief is not new and neither is love.

The seasons change the cemetery the way Antonio Vivaldi might have imagined. Autumn covers the grounds in burnt orange and gold. Winter strips everything bare and quiet. Spring arrives carefully, bringing green life back to the hillsides, and summer settles in heavy and warm beneath the shade of the old trees. The cemetery never really stays the same, yet somehow it always remains familiar.

That is one thing cemeteries can teach us quickly. In the end, all the titles disappear. The hockey legend, the labor lawyer, the banker, the mother, the neighbor down the block, the grandfather, the brother gone too soon and the father-in-law.

Eventually we all rest shoulder to shoulder.

I think about how short life can be and how quickly people become memories.

Bronswood has become important to me because it has taught me that cemeteries are not only for mourning.

Sometimes they are for maintenance. Maintenance of memory, maintenance of family and maintenance of the soul.

The older I get, the more I realize that I want to end up there someday. Not because it is fancy or expensive. Truth be told, I have never really lived in an expensive house or a high-end neighborhood during my life.

I want the Shepkids to have one place where the family can gather.

One place where they can visit their grandparents, their mother and their father.

A quiet piece of ground where they can come and think about life, talk to God, remember where they came from and maybe sit long enough to hear their own thoughts.

That idea means more to me now than it once did. Life humbles us that way.

Maybe part of growing older is understanding that even after divorce, disappointment and mistakes, family still matters. Maybe more than ever.

Because someday the Shepkids will walk those paths without us. I hope when they do, Bronswood gives them the same thing it has given me… Perspective.

The grabber section chalks out that we are approaching the second full moon of the month, a Blue Moon.

Don’t let that blue moon catch you standing alone without a dream in your heart...

May 25th, 2026

 “Uncommon valor was a common virtue.”

Admiral Chester Nimitz on the Marines at Iwo Jima

There are certain days in America that should always make us stand up tall.

Memorial Day is one of them.

Not because of a mattress sales at Tempur-Pedic or backyard beers at Uncle Ray’s or because today is the unofficial start of summer.

Because somewhere beneath all the noise and sunshine are rows and rows of white stones, folded flags and gold star families that never got their sons and daughters back.

The quote on today’s Chalkboard was about Iwo Jima. Young Americans climbing into hell on a black sand island because somebody had to do it.

Farm boys and factory workers. Kids from ethnic Chicago neighborhoods and small rural Indiana towns. Catholic boys carrying rosaries. Jews who had blood in the fight. Poor whites from coal country who could barely read. Black kids fighting for a country that didn’t always fight for them. Immigrants trying to become Americans by shedding blood for America.

Most of them were barely old enough to shave, but they were brave enough to fight for this country.

Yet when the moment came, courage became ordinary.

That is the meaning of the quote I chalked down this morning.

Not that valor was rare, but that it became expected.

Today, before the bratwursts hit the grill and before the first pitch at Comiskey, take a minute and remember somebody who never got the chance to grow old.

Somebody whose mother received a knock at the door. Somebody who left behind a baseball glove, a high school sweetheart, a future that barely began.

Freedom always costs somebody something.

Enjoy the cookout.

Laugh with your family.

Sit in the sunshine….

… But remember why you can.

May 24th, 2026

 My gramma brought her transistor radio out to the front porch so we could listen to the race.

We had ham sandwiches on white bread with bread and butter pickles and ice tea. What was unusual, my gramma always made us sit at the table for meals. They all started and ended in prayer.

This was the only time she let me bring my lunch to the porch.

Oh and I forgot to mention…

The ham was carved from last night’s supper. The bread was baked in my gramma’s oven and someone in the family made the pickles. All homemade and never any snacks.

The race was a fight between Danny Ongais and Al Unser. My favorite drivers, AJ Foyt and Johnny Rutherford were never a threat. Unser won the race and my gramma scolded me for saying I hated the Unser family.

I never felt at home in Indiana, but I sure would love one more afternoon on that front porch on Indianola Avenue in Broad Ripple.

Sunday Funday and I have two growlers of BuckleDown for the race and the family cookout.

“Gentlemen, start your engines….”

May 23rd, 2026

 Soft rain woke me up this morning. Backyard birds singing to each other before most people even poured their first cup of coffee.

Memorial Day weekend has arrived for 2026.

Another Indy 500 winner will be added to the Borg-Warner Trophy and summer officially begins. A summer filled with weddings, birthdays, funerals, hot afternoons and warm evenings. Days that will soon become faded memories from the summer we celebrated the semi-quincentennial. 250 years of stirring the American gumbo pot.

Labor Day is 107 days away.

One hundred and seven days to enjoy a summer that will mark beginnings, milestones, victories, defeats and unforeseen endings.

107 days of not putting it off until tomorrow. 107 days of not waiting for a better day because today is the better day.

Plant the flower.

Try the new Thai joint.

Take the drive.

107 days of making love, making friends and making goals. 107 days of dancing awkwardly and singing off-key. 107 days to pick up a wiffle ball bat, play catch in the alley and sit in a beer garden under string lights listening to John Prine songs.

This weekend is the beginning of the Summer of ’26.

And just like the summers of ’76, ’86 and ’96…

…it will become a distant memory sooner than we planned.

So take chances. Take the road trip for the pork tenderloin sandwich. Go to the street festival filled with people who don’t look like you.

Put the smile on the sun and look down at your shadow lying underneath your ass. Because before you know it, that shadow will be stretching long down the sidewalk.

These next 107 days should be filled with gusto, astonishment and high-pitched laughter.

May 22nd, 2026

 Yesterday I listened to the CBS jingle on Chicago’s WBBM radio for the final time.

One hundred years of affiliation and history gone with the flip of a corporate switch. Maybe that is just how business works now, but it still feels like somebody tore down an old neighborhood tavern to build a parking garage.

Morning radio today doesn’t sound like it used to. It used to keep you company. Voices had personality. DJs sounded like regular people drinking burnt studio coffee at 4:30 in the morning while telling you about traffic on the Ike and whether the Sox bullpen blew another one. Now half of it feels like noise designed by a committee.

The quote on the board this morning says pain is God’s megaphone to rouse a deaf world. Maybe that is why losing little traditions hits harder as you get older. They remind you time keeps moving whether you’re ready or not.

As for the grabber section… today belongs to the cooler.

National Cooler Day deserves more respect than it gets. I still have a cooler from the 1989 Bluesfest, back before I was handed the persona of Jumbo. Back then I was still just “Shep,” and somewhere along the way I scrawled that name across the lid with a Sharpie that never fully faded.

That cooler has survived lakefront parties, tailgates, road trips, picnics, heartbreaks, and enough cold Old Style cans to fill Comiskey Park.

The handle squeaks now, the plastic is worn, but like an old Chicago bartender, it still shows up and does its job without asking for applause.

Funny how objects become witnesses to our lives.

Today is another reminder that the old stuff mattered.

Old radios.

Old songs.

Old Sox fans.

Old coolers.

Old Arb Clerks.

Old voices.

May your cooler be filled with ice, gusto and astonishment.

May 20th, 2026

    

It is one of those anxious mornings where I have a shit ton on my mind and I can’t sleep.

Pet dogs, drink whiskey and don’t be a jagoff…

May 19th, 2026

 How happy is the blameless vestal’s lot… The world forgetting, by the world forgot.

That quote from Alexander Pope sounds peaceful on the surface, but I’m not so sure human beings were ever built to disappear quietly.

We all want rest from the noise. We all get tired of disappointment, heartbreak, drama, and trying to explain ourselves. There are days when disappearing from the world sounds like a form of mercy.

The truth is, none of us really want to be forgotten. We just want to be remembered correctly.

The older I get, the more I think about the people who came and went through the years. Some stay for decades, others drift through for one summer, one job, one neighborhood, one baseball season, one barstool conversation, one slow dance or that one night chance. Then life moves along and they slowly fade into memory.

What is strange is how entire lives eventually disappear from living memory. One day the last person who remembers your laugh, your stories, your bad habits, your favorite songs, your voice… will also be gone.

That is a hard truth to swallow on a Tuesday morning, but maybe that is why kindness matters so much.

Because kindness outlives witnesses.

A decent act keeps traveling long after the person who started it is gone. A kind father shapes his child. That child shapes another child. A teacher encourages one insecure kid who later encourages another insecure kid. The ripple keeps moving even when nobody remembers where or when it started.

Maybe the goal isn’t to be famous or immortal. Maybe the goal is simpler than that.

Leave enough goodness behind that the world stays kinder after you leave it.

Even after the last witness is gone.

May 18th, 2026

   The Monday before Memorial Day always feels like the front porch of summer. The screen door is about to swing open and let the festivities walk right in. The sun hangs around a little longer and the grills are adding flavor to the air.

People suddenly remember they were never meant to stay cooped up inside staring at walls and worrying about nonsense.

The Sox are above .500. The Cubs are above .500 and in Chicago…

…that alone can change the mood of an entire city.

You can feel it at the neighborhood tavern, on front stoops, around the softball fields and at backyard parties. Baseball matters around here because it gives working people something to believe in between paychecks and problems.

The older I get, the more I understand summertime isn’t really about vacations and swimming pools. It’s about permission.

Permission to breathe again.

Permission to sit outside after dark listening to a ballgame on the radio while lightning bugs float through the yard.

Permission to remember there was once a kid inside of you before mortgages, court dates, doctor bills and heartbreak took turns beating on the door.

The quote on the Chalkboard feels like life itself. One minute a man wants to disappear from the world and the next minute he is on his knees praying for one more good day.

That is the strange thing about being human. Even when we get tired, discouraged or beat up by life…

… summer still shows up like an old friend knocking on the door saying, “Come on outside, I have some bottle rockets.”

Find some gusto and astonishment on this warm hazy Monday..

May 17th, 2026

   Good morning Chalkheads, imagine going back one hundred years. Back to a time when almost everybody worked the land. Farmers, railroad workers and factory hands. People who measured a day by sweat instead of screen time.

Now imagine trying to explain modern jobs to those people. Tell a farmer or stockyard butcher from 1920 that one day there will be people called “sleep coaches.” People hired to teach exhausted adults how to fall asleep.

Then tell him somebody else earns a living talking into a phone camera as a TikTok influencer. He wouldn’t believe a word of it, but underneath the humor sits something important.

Every time technology changes the world, we make the exact same mistake. We obsess over the jobs that disappear. We rarely think about the jobs that get created afterward. Mostly because they don’t exist yet. They don’t even have names yet. Fear is easy because fear is specific.

AI is going to replace accountants, radiologists, drivers and maybe even the family doctor.

The fear comes with titles, headlines, charts, and predictions.

I’ve watched this happen in my own lifetime. When I first got into the futures business, the trading floor was chaos and hand signals. The only way to place a trade was to call a broker on the phone and have him physically execute the order in the pit. I stood shoulder to shoulder with hundreds of traders screaming prices at one another like a financial rugby scrum.

I started as an arb clerk flashing hand signals across a crowded trading floor. Then came computer screens. Suddenly the screaming started disappearing. Instead of flashing signals with my hands, I was typing buy and sell orders into a keyboard with a mouse sitting beside me.

Now a trader can sit in a cabana somewhere on the Mediterranean and place orders from a laptop. You don’t need to stand in a pit anymore. You don’t even need to be in Chicago. The entire industry changed.

Some jobs vanished completely. Floor brokers, runners, phone clerks and locals screaming in the pit all day long. In the death of the trading floor came new jobs. Programmers, IT nerds, quant traders, algorithm designers and electronic risk managers. Nobody on the trading floor in 1988 could have fully imagined what futures trading would become.

At the same time, my dream job was changing too. I always wanted to be the next Mike Royko. I wanted to write a daily newspaper column in Chicago. Back then the Sunday paper was practically a piece of furniture. Five inches thick with newsprint, comics, sports, classifieds, opinion pages, and department store ads falling onto the kitchen floor.

Now most people read the news on the phone while standing in line for coffee. Newspaper journalism has transformed completely. Some would say it collapsed, but something else happened too.

A guy like me can now write something in Riverside in the morning and have somebody across the country reading it five minutes later. No printing press, no delivery truck and no editor smoking cigarettes in a downtown newsroom.

Just an internet connection and a thought worth sharing. That would have sounded insane thirty years ago.

That is why I laugh a little when people talk about AI like it is the end of human work.

It’s not the end. It is just another transformation. Transformations are messy when you are living through them. The fear is always easy to identify because it already has a vocabulary. Nobody can clearly explain the jobs that will exist twenty years from now because those jobs are still waiting for the inventions that create them.

A farmer in 1920 could understand losing work to a tractor. What he couldn’t imagine was somebody earning a living managing social media accounts or helping strangers learn how to sleep.

Not because he lacked intelligence, but because all the inventions required to create those careers had not happened yet.

That is where we are now. Everybody is staring at the tractor. Nobody can yet see the seven inventions down the road. History says the jobs will come and CNBC agrees. One day somebody will be making a great living doing something we currently would laugh at.

Maybe my great grandson will work as a Screen Fatigue Recovery Specialist. A fancy title for a guy who tells exhausted people to go outside and touch grass. For all I know, my great granddaughter will make two million a year as a Professional AI Apology Writer. Some poor slob will yell at his robot refrigerator, and my bloodline will get paid to smooth things over.

The New Moon climbed into waxing crescent overnight as we move towards the next full moon on May 31st. Which will be a Blue Moon. Cubs and Sox go into the rubber match today in the Crosstown.

Go Chicago….

May 16th, 2026

        Funny thing about history.

Most countries, when they finally get the big stick, they use it like your drunk uncle at a summer cookout. They swing it around until somebody is bleeding.

One country beats another country and then comes the revenge parade. Burn the city, loot the silverware and humiliate the losers. Make sure their grandchildren are still apologizing for existing. Human beings are very creative when it comes to punishment.

Then along comes America after World War II. Now understand something. In 1945, the United States was sitting there holding all the cards. Europe was rubble and Japan was cooked, literally. Half the world looked like the alley behind an old Southside tavern after closing time. America had the atom bomb. Not only did they have it, they used it.

That meant America could have done what countries usually do when they get too much power. They could have stomped Germany and Japan into permanent mud holes and hung a KEEP OUT sign over the final operation.

History would have understood it too. Because that is what history expects from winners.

Instead, America did something so odd it almost sounds made up now. It rebuilt the countries it defeated.

Try explaining that to a Roman emperor sometime.

“Congratulations Caesar, after crushing Carthage, you will now help them rebuild factories and highways.”

The old boy probably would have fed you to lions for being drunk, but that is what happened. The United States pumped money into Europe. They helped rebuild Germany after the nazzies nearly destroyed it and they protected Japan from a thirsty Chikity China. America turned old enemies into trading partners.

Not because America suddenly became a saint, countries aren’t saints. Countries are more like precinct captains. They do favors because they expect something back in return.

America understood something after World War I that the rest of the world apparently missed. If you humiliate people long enough, eventually some maniac comes along promising revenge, and everybody starts marching again.

That is how you get another war. So, after World War II, America decided maybe it was smarter to build refrigerators in Germany than graveyards. Maybe prosperous people are easier to deal with than starving angry people.

Turns out that was good business too. Germany and Japan became an ally. American soldiers ended up protecting the same countries they had been shooting at a few years earlier.

Historically speaking, that’s nuts, but maybe that decision saved America from becoming another rotting empire held together only by fear and bullets.

Because fear works great for a while. So does a baseball bat, but eventually somebody bigger shows up with a bigger bat. The countries that last are usually the ones that figure out how to make other people want to stand next to them instead of hiding from them.

America wasn’t perfect then and sure as hell isn’t perfect now. Anybody telling you otherwise is either selling vacuum cleaners or running for office, but after World War II, America did one thing most powerful nations never do.

It won the war and then resisted acting like history’s usual thug. America has a chance to do the same act today.

A little Latin in the Grabber Section. It means Peace through Strength.

There might be the first bout with humidity and heat today. For you Chalkheads with Hip Hop Thighs, like me….

…. GoldBond those luscious lambchops and stay copacetic

May 14th, 2026

Percy Bysshe Shelley is warning us this morning against complacency.

He is telling us that the moment we start living off past victories instead of present effort, decline begins.

That applies to the athlete reliving high school glory. The businessman who stops adapting. Relationships maintained on old memories instead of current effort. Even nations that assume former greatness guarantees future success.

It is healthy to take self-examinations that keep us moving forward instead of sleeping on old applause.

The Greek term in the Grabber Section means know thyself. You can’t go wrong with a Greek philosopher and an English Romantic.

Big smile on the sun today.

Enjoy…..

May 13th, 2026

 HumpDay slides us into the middle of May. Memorial Day is the next blip on the calendar.

I put the day count on Labor Day in the Grabber Section to remind you Chalkheads that we have one less day until the end of summer.
            Let that morning sun smack your mug!

May 12th, 2026

     We can choose all we want, but after choice always comes the bill.

It is National Limerick Day and, much like life itself, limericks can be faithful, foolish and a bit lewd all at once. Here are two of my favorites that touch both ends of my spectrum.

God’s plan made a hopeful beginning.

But man spoiled his chances by sinning.

We trust that the story

Will end in God’s glory,

But at present the other side’s winning.

There was an old Countess of Bray,

And you might think it odd when I say,

That despite her high station

Rank and education,

She always spelled “C**t” with a K!

From a church pew to a barstool, astonishment and gusto can be found at both.

May 11th, 2026

    Some of the most valuable people in the world feel broken. They carry their world on their back just to make it to tomorrow.

   Just one more day. That is all I need, but as I creep toward a milestone year, I have learned something. It isn’t one more day, It is one less day.
          Coffee, prayer, stubbornness, integrity and duct tape keep it all together.
   Our value comes from what we have survived. Heartbreak, layoffs, buried parents, divorce papers, bad decisions and Mondays that felt impossible to wake up for.
   That is what makes us worth a million in prizes. Don’t sell yourself cheap, Chalkheads.
                         Lust for Life…

May 10th, 2026

          Here is a sad lady who tried her best to keep it together.

She grew up a middle child in a strict Catholic German family in Indiana. Born as the Depression turned into a World War. Her older sister became a nun. Several of her aunts were nuns.

Instead of pursuing her interests in music, she became a nun. It was a sad decision that affected the rest of her adulthood.

She left the nunnery and moved to Chicago. She got involved in her local parish in Edgewater and met her husband while teaching CCD.

Two lonely people united under their security blanket called the Catholic Church. They divorced after ten years of marriage with an only child to raise.

Like I said, she tried her best to hold things together.

Our moms are meant to be held up on a pedestal. After the Blessed Virgin Mary comes our mom. For my Jewish Brothers and Sisters, think Esther and Ruth.

Once we learn to wash the dirt off our knees and learn to make our own hot dogs, moms start fading from that prestigious stand in our lives.

Once we figure out mom being tired all the time means she was hungover again, we realize that lady that brought us into the world is human.

That lady that is twenty-five to thirty-five years older than us was going through the same shit show that we ended up living.

The same medical bills, the same pressure at work, the same aches and pains and the same flat tire on the Dan Ryan.

Underneath is the struggle with mental health. The battles with regret. The agony of not living to expectation. Throw motherhood on top and the perfect storm for chaos occurs.

There sure as hell isn't a manual for life. There isn’t a playbook for parenting either. Our moms raised us as best as they could with every ounce of love they had.

Add to the stress of worrying about their babies. Moms never stop worrying about their babies.

From the time they ride their bikes to the park and climb trees with their friends. To the times they sneak off to a kegger in the forest preserves. To the time they leave for adulthood. Moms never stop worrying about their babies.

During my mom’s last few weeks of life, she was more worried about my failing marriage and my oldest son’s recent diagnosis of autism. She was worried about me more than her own health.

She died worrying about me.

All moms worry about their children up until their final breath. Then they go to heaven and worry about us, but heaven is closer than our parents’ house growing up.

We mourn our mothers after they leave us. We shouldn’t though. They are with us forever. Becoming an adult son or daughter changes the perspective we have about our mothers.

They tried the best they could, and they never stopped worrying about their children. At one point they might fall off that pedestal. It is our job to place them back on it.

Our mothers placed the first stone in our foundation. Whatever strength we have started with them.

I love you Ma.

Happy Mother's Day to all my mom friends. You are heroes and never forget that.... good days and bad.

May 9th, 2026

 Good morning Chalkheads…

1995 is the Flashback year on XRT this morning. I started digging through the songs from the year I turned twenty-nine. There were a lot of choices, but I had to go with the one that scratched my head the most back then.

“Waterfalls” by TLC.

Funny thing is, thirty-one years later, the song actually makes more sense to me now than it did then.

Back in 1995, all I knew was that we kept hearing it over and over during a blurry bachelor party weekend down in New Orleans. A weekend fueled by bad decisions, too much booze, and the kind of confidence only young idiots from Chicago can carry into the South.

One buddy thought he was having a heart attack, so naturally he tried fixing it with a shrimp po’boy. Another genius dumped a tray of beers onto a table full of bikers. They were not impressed with the dipshits from Chicago.

…. and somewhere in the background, every bar and every cab seemed to be playing “Don’t go chasing waterfalls…”

The older I get, the more I realize that song wasn’t really about waterfalls at all. It was about people running toward chaos thinking they were chasing excitement. Sometimes the rivers and lakes you are used to are there for a reason. Stability doesn’t sound glamorous when you are young, but eventually you learn peace has value too.

Still… 1995 was a hell of a year for music.

My future wife was graduating high school. My old girlfriend was dating a Mormon. My parents still had advice, and I was down at the Chicago Board of Trade thinking I had life figured out in the bond room.

Saturday is a big radio day for me. WGN to WXRT to WDCB. Good radio keeps a guy company better than most people do.

Tonight I’m heading to dinner with my ex-wife and my mother-in-law (I didn’t divorce her) for Mother’s Day Eve. Wish me luck. No cocktails for the Oldman though, still on antibiotics. It is going to be a strictly sober performance.

Enjoy your Saturday, Chalkheads.

Go find a little gusto and astonishment out there today…

…just don’t go chasing waterfalls to find it.

May 8th, 2026

  Very few of you Chalkheads are going to know this lyric. It was written by the mailman from Maywood, John Prine.

Bronzed shoes represent keepsakes from our past. A rearview mirror is literally where we look backward while moving forward.

We often glorify the past, but while admiring it, we ignore the regrets attached to it.

Blind spots in life become old relationships we romanticize. Younger days we remember as better than they really were. Mistakes that we tend to polish into shining legends.

Don’t gaze too long at those decorated memories, because they might keep you from creating current moments worth remembering.

The rearview mirror is smaller than the front windshield for a reason.

One memory worth hanging onto is celebrated today. Never let it fade that today we honor the Allied victory over the nazzies in the Second World War, V-E Day.

Freedom isn’t inherited like your grandfather’s pocket watch. Every generation has to protect our freedom, respect it, and remember what it cost.

Let’s finish the week strong. Don’t forget about your momma this weekend.