ALL CHALKBOARDS

Saturday, September 20, 2025

September 20th, 2025

 “Friendship shouldn’t be a battle.”

That is the chalk today, and it is not just a throwaway line. Back in 1975, the band War dropped a song called Why Can’t We Be Friends? A tune that asked that question thirty-six times in three minutes. It was playful, funky, and deceptively simple.
Let us look closer at the lyrics and you find lines that cut to the bone: “The color of your skin don’t matter to me, as long as we can live in harmony.” That’s not just a rhyme. That’s a plea.
I think about that song when I look at the divide we are in today. Families that won’t sit at the same table because one voted blue and the other voted red. Friends who won’t pick up the phone because four years under one president meant agreeing with Dad, and the next four meant screaming at Uncle Steven.
We are slicing life into chapters: childhood, teenager, college, marriage, middle age, gray hair...
...and each one feels shorter than the last.
And now we are letting politics erase the people who matter most inside those chapters.
Unless your friend is consumed by hate. Someone who lives for argument, who is bombastic and cruel in every conversation, then you’ve got something not worth saving.
If it is a Republican friend who stood at your parents’ wake, or a Democrat who called during your divorce to check in, then you can’t throw that away over an election cycle.
That is when you brush the difference aside and carry that friendship into 2026. Because in the long run, what do you really want? To stand alone in the name of being right, or to sit with someone who was there when you needed them?
Our time here is short. Break it into decades, into eras, and you will see just how short it really is. Friends are the glue in those years. The ones who walk with you in Chinatown, who share a drink, who make you laugh when you’re broke and standing in line. Friends who knew you when you were working for the CIA. Those are the ones you keep.
Today's Grabber Section: Tomorrow we will celebrate Earth, Wind & Fire and remember the 21st of September. I want it to be Jumbo who asks you, Do you remember?
Today, though, the 20th is going to be a cloudy day.
I successfully earwormed you Chalkheads with two songs from the same decade, with the same message...
... it’s not about winning or losing. It’s about choosing harmony over division. Why can’t we be friends in the key that our souls were singing?!?!?!




Friday, September 19, 2025

September 19th, 2025

 Today is POW/MIA Recognition Day. We hang the flag, we salute, we nod.

Steinbeck’s words, “You can only understand people if you feel them in yourself," remind us that it can’t stop at a ceremony. To honor someone missing, you need to imagine it was your father, your brother, the neighborhood kid who never came home. That is the only way it cuts deep enough to matter.
We should carry that same weight when we look at each other on the street. Since the covid flu, the world has been running on a short fuse and the smartphone era has intensified it. Everybody is shouting into the glow of their screen, pumping out their hot takes like smoke from a glue factory. You can’t miss the loudmouth liberals and the caustic conservatives; they are too busy telling us how bad it all is.
They aren’t the ones I worry about.
It is the quiet ones that need our attention.
The guy staring down at the sidewalk, so he doesn’t have to meet a pair of eyes. The woman sitting in her car in the parking lot a little longer before heading inside. The distraught who deleted the text instead of hitting send. That’s where the hurt lives now, behind lowered heads and swallowed words.
Doing a kind act doesn’t magically make you a kind person. Steinbeck’s line says the real work is in feeling someone’s burden in your own chest. That is harder than dropping a few dollars in a GoFundMe or clicking a like. It is taking a beat, looking at the stranger in front of you, and asking, what if that was me?
The flag for the missing flies high today. Let it remind us that every day, in every ordinary place, people are missing as well. Not from a war overseas, but from the simple recognition that they really do matter. Our job is to see them, to understand them and not let anyone slip through the cracks in this short time we have together.
Happy Friday Chalkheads, make sure Eleanor Rigby isn't missing in action this weekend...




Thursday, September 18, 2025

September 18th, 2025

    When you are a single father, you think about what you are going to leave behind. Not just in the bank, not just in the will, but in the marrow.

You can hand down a car, a watch, a pile of bills, but those things rust and fade. What stays are the lessons your kids carry after you are gone. Everything left from my parents' lives are packed away in three boxes in the back of a closet, but I chalk often the words passed down from my Oldman and my Ma.
Honesty is the richest of them all. Not the Hallmark version, not the kind that pats itself on the back, but the tough honesty that leaves a scar. The kind where you look your son in the eye and admit you blew it. The kind where you tell your daughter the truth even when you know it will make her mad. The kind where you swallow your pride and say, “I was wrong.”
On the trading floor, plenty of guys tried to bullshit their way through the session. They lasted about as long as a margin call. The ones who stood the test of time were the ones who kept their word.
Same goes for fathers. A kid can smell a lie from a mile away, and once you lose that trust, it is hell getting it back.
So you build your legacy brick by brick, not with speeches or trophies, but with little truths stacked over years. Maybe it doesn’t look like much to outsiders, but for your kids it is everything. It’s the foundation they stand on when their world tilts.
Tonight the moon is in its waning crescent. Thin, fading, almost gone. A reminder that light comes and goes, but the dark teaches too.
You don’t have to be perfect.
You just have to be honest.

That is the kind of light that doesn’t burn out.

Wednesday, September 17, 2025

September 17th, 2025

 When I was a kid in the ’70s, you couldn’t escape Barbra Streisand’s “The Way We Were.”

It was everywhere, even in NFL Films highlights. It wasn’t my song, it was a mom song, the kind of tune ladies born in the 1930s carried like a locket. Still, I filed it away in the soundtrack of my life. I had a huge crush on Streisand, and maybe that’s why, whenever the song plays, my own life rolls back in slow motion like a highlight reel. I don’t know why I kept it, but it stuck.
The song is on the Chalkboard today because Robert Redford died. Redford was the crush for all the moms of that generation. Mine adored him in The Sting and Butch Cassidy. Thank goodness he wasn’t cast in Love Story, if he had ruined Ryan O’Neal’s role, it would have been criminal.
I will say this... I never forgave him for The Great Gatsby. That is my favorite book, and Redford hijacked Jay Gatsby. He was Hollywood’s Baskin-Robbins flavor of the month, and Fitzgerald had to have been turning in his grave watching Redford paste a golden-boy smile on the most tragic dreamer in American literature.
For me, that was unforgivable.
So why does his death even matter to me? Not because of Redford himself. What stings is that every time another one of those icons fades...
...another piece of my mom goes with them.
Her Hollywood crushes, her movies, her hug, her soundtrack, her era, her phone conversations on the kitchen telephone. They are stitched into my memories, same as mine are stitched into the Shepkids’.
Today's Grabber section has some Latin.
Explicare te ipsum.
Explain yourself.
Today we don’t do that. We are reduced to profiles, followers and highlight reels. Nobody takes the time to unfold who they really are. I don’t need another social media update.
Just tell me something new. Tell me what made you fart in the elevator.
Let me finish chalking.... a smile on the sun. An eighty-four on September 17th and an astonishing memory to make.
Memories... Light the corners of my mind. Misty watercolor memories. of the way we were.




Tuesday, September 16, 2025

September 16th, 2025

     The old Englishman said it clean: “It is not in the stars to hold our destiny but in ourselves.” Shakespeare dressed it up in iambic pentameter, but here in Cook County we know the translation. Nobody is coming to save you. The moon and the stars don’t give a damn whether you sink or swim.

Studs Terkel would have called it the gospel of the working stiff. The guy in the steel mill with the punch clock, the nurse with the double shift or the kid hustling his way through night school to get a law degree. All of them writing their own story, one tired morning after another. No horoscope ever paid the rent.
Mike Royko, God bless him, he would laugh at the notion that fate was going to bail you out. He would point at the guy bellyaching at the end of the bar and say, “Buddy, if you’re waiting on destiny, you’re already late for work.”
Same went for the trading pits. The opening bell brought the floor to attention, and it wasn’t fate buying the lows or selling the highs. Luck never built a destiny. The ones who walked out with their wallet still in their pocket were the ones who went the distance and stayed consistent, day after day, until the closing bell.
Call it Shakespearean or call it Chicago common sense...
... you own your choices. You build your life.
The stars on Armitage are just orangey streetlights overhead.
It is going to be a gorgeous Taco Tuesday and it happens to be National Guacamole Day. Complete your day with some tortilla chips and a deep bowl of gwak!





September 15th, 2025

 I came across today’s quote and thought about Newton’s cradle.

Do you remember that device that might have been on the principal’s desk? Maybe in your therapist's office? My Oldman had one on a bookshelf. Five metal balls hanging from a rocker. One swings out, then returns to center, passing its force along until the ball on the other end clicks to the other side. The three in the middle stay steady, holding the balance.
I’m kind of like Newton’s cradle, but I prefer to use Jumbo’s Cafeteria as my example. Fitting, since I am both a Cafeteria Catholic and a Cafeteria Republican. My religion and politics are like a buffet line where I get to pick and choose my beliefs. Beliefs that would probably get me excommunicated by Rome and wandering aimlessly in D.C.
I am not going to chalk about what I support or don’t support. I will just let my balls click and clack from side to side and spread Jumbo Love wherever I go.
Someday I will have to answer to Pappa God for the stupid shit I’ve done, but until then, I will try my damndest to push a little positive momentum down both sides of the street.
Today is the last seven o’clock sunset until Saint Patrick’s Day. I know it is kind of a dick move, but the Grabber section gives you a heads-up that is not immensely popular. The dreaded end of Daylight Savings Time.
Days get long, days get short. It all balances out in the middle. Just like that Newton’s cradle on Father Kelly’s desk.




Sunday, September 14, 2025

September 14th, 2025

 I want to step away from the political viewpoints of the major event from last week. I am not asking my Liberal Chalkheads or my Conservative Chalkheads to stand on a soapbox here.

Out of everything that happened, one thing stood out at me. A father turned his son in to authorities.
Let’s take Matt Robinson’s perspective.
I am a father.
That word once meant ballgames, scraped knees, fixing bikes, and waiting in the car after football practice, but now it means something I never imagined. It means looking at a grainy photo on the news, recognizing my own son’s face, and hearing him admit, with his head down, that yes, it is him. It means standing in a kitchen where the silence feels like a casket and realizing the boy I raised is now the man who took another man’s life.
I did what I had to do, but don’t think for a second it was easy. The world will say I chose courage over blood, and maybe that is true, but they don’t know how deep it cuts to hand your son over to the very people who will cage him, maybe even kill him. My duty as a father didn’t stop when I saw those photos, it widened. It became more about truth, about justice, about making sure more fathers didn’t get that midnight knock on the door.
Every parent prays their child won’t be the headline, won’t be the mugshot, won’t fall into the pit. We hope for the best and fear the worst, and one day the worst knocked on my door. I could have looked away, made excuses, clung to the belief that my boy was still good inside, but belief is not blindness.
I had to face what was in front of me and in that moment, I asked myself what God would have me do. What my faith teaches about truth and responsibility. Faith without work is dead. It wasn’t enough to pray in silence. I called in a pastor and leaned on my faith.
Because fatherhood isn’t only about protecting your own. It's about protecting everyone else as well.
Of course there were signs. A shadow here, a silence there, a drift into corners of anger that I didn’t fully understand.
Did I miss them?
Did I ignore them?
I’ll carry those questions forever.
Every father wonders if he should have listened harder, asked again, pushed more, fought more. For me it is too late to change that story, but maybe not for another dad out there. Now I live in the aftermath. I didn’t bury my son in a grave, but I buried him in another way...
...behind walls, behind chains, behind a justice system that will not give him back.
Parents who bury their children grieve with flowers on the grass. I will now grieve every morning with the knowledge that my son is alive but lost to me forever. Prison is another kind of coffin and I am the one who closed the lid.
So, what will my legacy be?
Some will say I did the right thing, that I was a “father of justice,” but what will my son say? What will he carry, knowing it was his own father who handed him over? I don’t know.
All I know is I could not let him run from the law, from the truth, from himself. They say the hardest thing a parent can do is bury their child, and maybe that is true, but I have done something just as impossible. I have buried my son alive into the cold earth of the state, knowing he may never come out. There is no prayer strong enough to soften that blow, no word that can carry the weight. There is only the hope that one day, because of what I did, another father will never have to face this choice.
That is it Chalkheads! I didn't look at this from a political viewpoint, but by a perspective that I could relate to... Fatherhood.
Let's shake away from today's lesson in life and reach for some gusto. It is Sunday Funday and we have some gridiron going on.
Grabber section tells you how much time you have to pick out a trick or treat costume. It also gives you the timeline to prepare for the turkey dinner debates.
Go out there today and measure how long your shadow is getting as Chicagoland sunsets are creeping for the last couple nights after seven o'clock!




Saturday, September 13, 2025

September 13th, 2025

    I was sitting on the balcony watching the sun drop behind the courtyard building across the street. The September heat finally loosening its grip as the sun waved bye-bye. The bourbon in my hand was cooling against a single ice chip, doing its job as much as I was letting it.

One by one, the Shepkids wandered out to check on their Oldman. Each with their own little request, each reminding me that even on quiet nights, fatherhood doesn’t punch a clock.
George poked his head out first. “You okay, Big Man? Can you make some popcorn for me?” That is George, checking in, steady as he goes, with a snack request that is as much ritual as his favorite snack is on a Friday night.
Hazel followed, asking if I could make her dinonuggies. The girl knows what she wants and sees no reason not to ask for it.
Then Fritz came out, not with food in mind but a shower. Typical middle child move... practical, reserved, and somehow the one that is stuck to be the glue of the family.
Fritz sat down a moment to shoot the shit.
I had shuffle running on Spotify, playing through my list of favorite tunes. Fritz paused, listened, then asked, “What are you listening to?” I told him it was the song I played every time his mom was giving birth to him, his brother, and his sister... Kate Bush’s “This Woman’s Work.”
It was my shorthand way of saying that this was the soundtrack to your arrival into my life. He blinked, then asked, “You actually listened to this song every time Mom had us?”
Truth is, the song played when I was asked to leave the delivery room while the epidural was happening.
Why ruin the poetry of it?
I let him believe the tune was pouring out as he squeezed his way into the world. Damn if that late-’80s song doesn’t still make me cry, still make me run the reel of what-ifs in my head, but screw the what-ifs.
Those three days, each birth, were the most magical days of my life. Kate Bush nailed the feeling better than I ever could.
Someday, I will tell them the whole story. That the one born on July 24th was conceived while their mom and I wore Halloween costumes, her favorite holiday. That the two knuckleheads arrived out of Thanksgiving spirit, which has always been my holiday of choice. Those details can wait. For now, I’ll let the myth live a little longer.
Fritz got his shower.
Hazel settled for a yogurt and a banana instead of her nuggets.
George munched on Orville Redenbacher.
And me?
I finished my bourbon, leaned back, and let the stars shine over Riverside and the Divorced Dad District. It wasn’t about popcorn or showers or Spotify or dinonuggies. It was about them showing up, one by one, orbiting the Oldman with their simple asks. Proof that in all the things I should’ve done, there is one thing I never failed at...
...I always showed up for them.
Saturday brings rugby and the halfway point to Saint Patrick's Day. If you don't have anything to do... Go out to Lemont and watch the Blaze ruck or go to The James Joyce and hear the bagpipes fill the air. 1983 is Flashback on XRT today.




Friday, September 12, 2025

September 12th, 2025

    Life has a way of serving me a lesson in humility. A sign, an event, sometimes even a déjà vu. Something always shows up to put me in my place. Whenever I start to complain or wallow, the world finds a way to knock me down a peg and remind me to pull my head out of my ass. That’s the heart of today’s quote: there is always perspective if you’re willing to see it.

Since it’s National Milkshake Day, I will add this... give me a malt over a shake any day. But truth is, either one is a win.




Thursday, September 11, 2025

September 11, 2001: A Morning lost


   I was thirty-five years old on September 11th, 2001. By then, I had been working in the bond room at the Chicago Board of Trade long enough to know the rhythm of a trading day. The morning rituals, the camaraderie, the jokes, the way the floor woke up and came alive with the opening bell. The scream of down ticks and the roar of up ticks.

What I did not know, what none of us knew, was that this particular Tuesday morning would be unlike any other. A day when the world would shift. A day when a colleague’s voice on the other end of my headset would vanish forever.
It started out like every other workday.
The congress L carried me from Oak Park into the city, the train rattling over familiar tracks across the westside, the skyline growing larger at every stop. It was warm, unseasonably so, the kind of September morning that makes you wonder if summer has not quite let go yet. I walked into the Loop, coffee in hand, morning paper under my arm, White Sox cap pulled to my brow and into the Board of Trade building I went. The routine was comforting as I swiped through the turnstiles, nodding at the security guards, taking the escalator to the fourth floor.
Once I got up to the trading floor, it was like slipping into an old pair of shoes. I pulled on my trading jacket, shoved a water bottle into the pocket, and took that first deep breath of pit air… sweat, cologne, newspaper print, coffee, and adrenaline. I made the rounds, shaking hands and tossing hellos to my customers. Sharing a few quick jokes with the guys in the pit. That was our ritual, too, grease the wheels with camaraderie before the bell.
Then I grabbed my headset. That headset was my lifeline. Every day it plugged me into two worlds. One voice here in Chicago, Jeff, a cash trader with Rosenthal and one voice in New York, Jimmy O’Brien, OB, working as a bond broker at Cantor Fitzgerald.
Jimmy was thirty-three, a husband, a father, living in Park Slope, Brooklyn. He was the kind of guy who could bust your balls and make you laugh in the same breath. He had that unmistakable New York accent that could cut through the chaos of the markets.
Jeff was not on yet that morning, so it was just me and Jimmy shooting the shit as we waited for the 7:20 open. The conversation was easy, the kind of small talk that builds friendships across miles of wire. He told me he walked his dogs to Prospect Park and went home. He took it easy with his family, watching the Giants play the Broncos on Monday Night Football.
I told him about my softball game, how I struck out and had to buy the team a round of overpriced shots. He laughed hard, really leaned into it, busting my balls with that Brooklyn swagger. We had a running thing about me being the big Chicago Midwest hayseed guy and him being the marble mouth New Yorker. That morning was no different. For a few minutes, it felt like every other day.
Then Jeff clicked in. The trio was complete, and we went to work.
The open was quiet. No big numbers, no market shockers, just another Tuesday. I was quoting bids and offers to Jeff, feeding him prices while Jimmy worked orders in the cash market. In the background I could hear Jeff and OB volleying back and forth, moving size, pushing orders. The headset was alive with their voices, and I was right in the middle, the bridge between Chicago and New York.
And then… silence.
Jeff suddenly shouted, “OB, you there? What the fuck—OB, am I filled?”
But OB did not answer.
I looked up at the Jumbotron on the trading floor. The image hit me like a punch to the chest. One of the World Trade Center towers had black smoke pouring from the side. My stomach dropped.
I told Jeff, “Flip on CNBC. Look at what is going on at the Trade Center right now.”
An uncomfortable pause and then the line went dead. Jeff had hung up, no doubt trying to reach OB directly, trying to figure out if he was okay. Trying to make sure that trade was not the last thing they ever worked together.
I took off my headset and stared at the screen. The pit went still. Hundreds of traders, usually loud and raucous, stood frozen, eyes glued to the smoke curling out of that tower. The air felt thick, like we had all stepped into a different world.
Phones started ringing across the floor. Customers liquidated positions, locals got flat, and one by one, traders and clerks slipped out of the building. None of us knew what was next. Was Chicago the next target? Was the Sears Tower, The Board of Trade, the Federal building in the crosshairs? We had no roadmap for what we were seeing.
The Board of Trade did not close right away. That is something I will never forget. While chaos unfolded on live TV, the exchange dragged its feet, waiting. Finally, after the second tower was hit, after news of the Pentagon attack broke and another plane was unaccounted for, the order came down the markets would shut immediately.
That was it. The spell broke.
We surged toward the exits, jackets still on, papers abandoned, all of us funneling down escalators, through the coatroom, out into the streets. Hundreds of people, all at once, pushing into the Loop, desperate to get out of downtown. I bolted for the Congress stop, hopped the subway, and sat in a train car full of pale, stunned faces.
The ride out to Oak Park was a blur. Underground for stretches, disconnected from news, we sat in silence. By the time the train broke into daylight near Halsted, word rippled through that one of the towers had collapsed. Nobody was sure which one. North, South, it did not matter. A building I had seen with my own eyes was gone. Thousands of people were inside. My friend might have been one of them.
Back in Oak Park, the sky was shockingly blue. Thin, wispy clouds floated like nothing had happened. The air smelled of late summer, almost sweet like corn. It was surreal. I did not go straight home. Instead, I cut into Ascension Catholic Church, my parish. The doors were wide open. Inside, it was empty. I lit a candle and knelt, the waxy scent filling the silence. I prayed, though my mind was a storm. Tears came, hot and heavy. I did not know if OB was alive. Deep down, I already knew.
The sound of school bells rang outside. Children poured into the playground, screaming, laughing, chasing each other like it was any other recess. Their joy was piercing. I remember thinking, we just lost our comfortable world. Childhood innocence colliding with the harshness of what had just happened. America was under attack. We weren’t naïve anymore.
I walked the five blocks home slowly, still in a daze. It wasn’t even noon yet, but I craved a margarita from the Mexican place up the street. The bar wasn’t open. So, I sat alone in my apartment, flipping through channels, watching replays of the towers falling, trying to piece together scraps of information. I called colleagues, I called friends and I tried to reach OB over and over again. Nothing.
My girlfriend, the woman who would later become my wife, was taking graduate classes at DePaul that morning. She caught a train out to Oak Park as soon as she could. Her father, my future father-in-law, had been in his law office in the Loop, but he made it home safely, too. We checked in with family and friends, one by one, ticking names off a mental list, making sure they were accounted for.
But there was one name I couldn’t cross off.
Jimmy O’Brien didn’t make it out.
That realization sank in like concrete. He had been on the other end of my headset one minute, laughing about me striking out in softball, and the next, silence, smoke, collapse... Gone.
So much happened that morning, and by noon it felt like the world had aged a century. The millennium came in like a boxer rocked by an unseen uppercut. The trading floor, that sacred stage of my working life, was suddenly small and powerless. The rituals of yelling and screaming and hand signals seemed meaningless against the images of towers crumbling, lives ending and innocence lost.
I think back on that day often, not just the horror, but the details. The water bottle in my jacket pocket. The sound of OB’s last laugh. The pictures on the Jumbotron when the first smoke appeared. The rush of bodies at the turnstiles. The blue September sky in Oak Park. The empty church. The children’s laughter. The silence of my apartment.
September 11th, 2001 was the day America changed, but for me, it was the day I lost a colleague and a friend. The day a Brooklyn accent went silent forever on my headset. Years later they found six inches of Jimmy’s shinbone. September 11th quickly moves further away with time. I age through life continuing my career, getting married, having children, getting a divorce and OB will always be thirty-three.
Years throw their elbows, but the story keeps its shape. Sometimes I think about that last conversation with OB and how absolutely nothing in it would have made the highlight reel of our lives. Walking the dogs, watching football and me striking out like a bum. That is the point. The day before a world ends is never an opera, it is a soft shoe. It is a laugh you think you will hear again in ten minutes. It is a man in Park Slope walking back from Prospect Park with two leashes in one hand and a bottle of beer in the other, thinking about ordinary things. It is a Chicago guy playing softball with his buddies from the neighborhood, thinking about ordinary things. Two men, two cities, one headset.

 

 


September 11th, 2025

                                                             May their memory be a blessing

Sunrise this morning is at 6:27



Wednesday, September 10, 2025

September 10th, 2025

 What if tonight is the last night you go to bed?

That is what September 10th is. It is the last night thousands of people went to sleep thinking they would wake up Tuesday morning, kiss their kids, walk the dog, grab a coffee, make the opening bell and have a normal day.
But they didn’t.
They had their last day.
For me, September 10th, 2001, was softball night. I pulled on a pair of softball pants, threw on my Wild Turkey jersey, and drove over to Ridgeland Common for the first game of the fall season. Oak Park autumn ball isn’t like summer ball, the games move fast. Every batter starts with a 1-and-1 count. By the end of the season, we are playing under stadium lights at 9:30 at night with wind chills, so shaving off pitches was survival.
First at-bat, I step in, brain on autopilot, and rope one down the first-base line foul. That’s strike two. Next pitch floats in, high and lazy, clear ball… ump rings me up. I forgot about the fall pitch count and struck out without taking a last swing.
The Wild Turkeys bench exploded... not angry, but delighted. Because in our dugout, you strike out, you buy shots, and back in 2001, Irish car bombs were the weapon of choice. Twelve players, plus girlfriends, spouses, hangers-on… two hundred bucks evaporated out of my wallet before I left the field. That was my Monday night, September 10th.
The next morning, headset on before the open, I checked in with Jeff at Rosenthal and Jimmy O’Brien from Cantor Fitz. Brooklyn guy, voice like gravel and traffic horns.
“So, what’d you do last night, Jombo? More of that Chicago beer-league hayseed softball?”
I told him about the strikeout, the shots, the damage to my wallet. He laughed so hard I can hear his coffee spill.
Half an hour later, an airplane went through Jimmy’s trading room.
That was it.
One minute, we are busting balls about Irish car bombs and softball. Next minute, he’s gone. He never called back. Never got to walk his dogs again. Never held his five-week-old son again. Jimmy’s name is carved in marble at Ground Zero now.
That is why this word is in the Grabber section today: Squander.
I never stepped into another batter’s box after that and I have never squandered a day since. That is why I write these chalkboards. That is why I point out the sun, the moon, the planets, the stars. That is why I use the word astonishing so much. Because every damn day is.
September 10th is a day to live for the people who didn’t get September 12th. Take the dogs for a walk. Call your parents if you still can. Meet a friend for oysters. Order the cannoli and the glass of port. Tell your kids you love them twice, not once.
Jimmy O’Brien’s children are adults now. He never had the chance to watch them grow up and that is why we never forget.
Because one day, without warning, we will all have our Monday night.
Don’t squander today.




Tuesday, September 9, 2025

September 9th, 2025

 The Cave, the Treasure, and the 14,471 Day Drought....

Fourteen thousand, four hundred seventy-one days.
That is how long it has been since the Chicago Bears won Super Bowl XX. Back when Walter Payton still carried the rock, Ditka still chewed gum like it owed him money, and McMahon’s headband was cooler than all the quarterbacks we have had since.
Today’s chalkboard says, “The cave you fear to enter holds the treasure you seek.” Well, around here, that cave is called Soldier Field. Every September, Chicago walks right up to that dark entrance like a pack of suckers with season tickets and old memories. We squint past the shadows, hoping this year, maybe this year, we find the damn treasure.
Only ghosts live in that toilet seat stadium. Duerson, Payton, McMichael and The Super Bowl Shuffle. The monsters have left, and the cave swallowed the roar. What is left is a city leaning on hope the way a drunk leans on the bar at closing time. Praying that the next round is the one that finally changes everything.
Fourteen thousand, four hundred seventy-one days since the last title. One more September, one more chance to chase the treasure.
If you’re scared to walk into the cave again, you’re not alone....
...but here in Chicagoland, we keep walking in because that is what this city does, we show up.
Because we are the Bears shuffling crew and we don’t stop fighting for our Monsters of the Midway, even if it kills us.




Monday, September 8, 2025

September 8th, 2025

 It is going to be a long day. I woke up at two o’clock in the morning and if I stay up to watch the Bears… Monday will be longer the Canterbury Tales.

Tuesday will be tired, but who can sleep when we are in the middle of such a gorgeous end of summer, beginning of autumn.
From the full moon to the Monsters of the Midway, it’s going to be a miraculous Monday.
Bear Down.




September 7th, 2025

      Being a baseball fan in Chicago is like being in a bad marriage. You keep showing up, keep believing, and somehow keep getting your heart stomped on. We finally got a couple of miracles in this lifetime, Sox in 2005, Cubs in 2016. That is more than most of our parents and grandparents ever got. They lived and died waiting for parades that never came.

On the South Side, the Sox are just about to put us out of our misery. Up north, the Cubs still have “a chance,” but don’t kid yourself, being a Cub fan just means your disappointment shows up in September instead of June.
Then there are the Bears... God help us.
Monday night kicks off another season of Monsters of the Midway mythology, and it’s been forty years since they were kings. As of today, they’re technically “in the hunt” for a Super Bowl. By Tuesday morning, that hunt will look more like a crime scene.