I’M SITTING AT MY DESK in my home office. It’s the first Friday in May. The windows have been open since I settled in with my second cup of coffee and reluctantly flipped open my laptop. Cardinals, Bluejays, and Chickadees sing over each other nearby, serving as constant reminders of the vibrant energy across the city.
The last two days, I’ve bounced back and forth between the office and the world’s most famous race track. Today, however, the blinders are on.
It’s difficult to lock in. The kids are out of school. Everyone you know is where you want to be. One only gets so many Derby weeks in his life.
Suddenly, the room grew dark. The wind picked up and rain began pelting the window screens. I sprung up to close them shut, only to witness a wicker chair blow across my driveway, carrying three flower pots with it. Shit.
Instinctively, I grabbed the remote and threw on the local Kentucky Oaks coverage. The WAVE3 cameras captured the chaos. Thousands of pink clad, fascinator-wearing spectators ran for cover as the proceedings momentarily halted at Churchill Downs.
AS A GRADUATE of Louisville’s Male High School, there’s a lot to live up to. Fellow alumni include Dr. Dunkenstein himself — Darrell Griffith — and Louis Brandeis, the first Jewish Supreme Court justice.
My favorite Male grad, though, is the godfather of Gonzo Journalism, Hunter S. Thompson.
As the story goes, Thompson earned and embraced the “Gonzo” monniker after publishing his satirical first-person narrative The Kentucky Derby is Decadent and Depraved.
The Louisville native had a pulse on the city around Derby time as well as anyone. His 1970 piece weaves a narrative of drunkenness, debauchery, and delirium as he navigates the Derby’s 96th running with a London sketch artist, who may as well have gotten on a plane at Heathrow and stepped off on Jupiter.
All I knew about him was that this was his first visit to the United States, Thompson explained. And the more I pondered that fact, the more it gave me fear. Would he bear up under the heinous culture shock of being lifted out of London and plunged into a drunken mob scene at the Kentucky Derby? There was no way of knowing.
Thompson details the Derby the only way a true native could; With biting cynicism and ardent assimilation.
55 years later, his summation of a colleague’s first embrace with Louisville stands the test of time.
Just keep in mind for the next few days that we’re in Louisville, Kentucky. Not London. Not even New York. This is a weird place.
BACK AT THE TRACK, folks were returning to their boxes.
I always thought that “box” was a peculiar way to describe where most grandstand-goers have assigned seats at Churchill Downs. In the adjacent L&N Stadium, a 62,000 seat shrine to college football, a box is more of a temperature controlled lounge with leather couches, private televisions, a dry bar, and a near-perfect view of the action. At Churchill Downs, box more aptly describes an 8-foot by 6-foot metal railing that features 6 folding chairs- Comfort sold separately.
The pandemonium that accompanies a weather event at Churchill Downs is unlike anything you’ll see.
In the clubhouse and grandstand areas, bourbon and 22-dollar lillies go flying as drunken strangers run to huddle together, attempting to cover their couture dresses and designer sports coats with $1 plastic ponchos.
But moments later, the sun is out, the ponchos are doubling as seat covers, cigars are being re-lit, and the money is rolling in fast as ever.
It was call to the post time at Oaks. I averted my eyes from the screen momentarily, threw an exacta box on the two favorites, and re-focused my gaze on the three computer monitors in front of me.
A stillness fell over my house a few miles away and I cracked the windows again. The birds resumed singing as the damp May air wofted into the room.
When I look up again, the horses are off and barrelling at 40 miles per hour as 100,000 drunken, soaked, pink-clad patrons drown out the PA.
A LOT HAS CHANGED in the 55-year period since Depraved hit the newstands as a feature piece in the short-lived Scanlan’s Magazine.
Let me rephrase that: All but everything has changed — Churchill Downs not withstanding.
The clubhouse nearly dwarfs the iconic Twin Spires, which still stand proudly as a must-have photo opp. The track now boasts the world’s largest ultra-high definition video board. It takes up over 15,000 square feet and weighs 1.2 million pounds. The premium boxes and suites have been updated and upgraded, the first turn saw a 7,100 seat renovation with trackside access, and everything from luxury meeting rooms to the renowned “backside” is newer, bigger, better – More monumental.
Perhaps the most luxurious, and definitely the most feather ruffling, revamping was done to the fabled Paddock.
Thompson described the track’s most intimate area as a place where people go to be seen.
The Paddock bar is probably the best place in the track to sit and watch faces. Nobody minds being stared at; that’s what they’re in there for. Some people spend most of their time in the Paddock; they can hunker down at one of the many wooden tables, lean back in a comfortable chair and watch the ever-changing odds flash up and down on the big tote board outside the window.
Formerly a cobblestone-lined town square known as a great meet up location and elite spot to brush up with horses, jockeys, and trainers, the paddock showing has always been a pre-race tradition. Before televisions and technology, the only way to get a glimpse of the ponies before the race was to line the rail at the paddock and watch closely as the participants were paraded in.
A buddy in high school once leaned up against the rail, drunkenly inhaled his cigar, and explained “if he’s dancin’, he’s nervous. Poopin? He’s good to go.”
Can’t argue with that logic.
But it’s 2025, dammit, and if the greatest champions in our sport can’t have the ultimate spotlight, then what are we even doin’ here?
Enter the new “paddock”. More of a coliseum if you ask me.
The horses, riders, and their posses enter the ring via tunnel now. Surrounded on all sides. The horse stalls are larger — More glamorous. They back up to windows that lead to a room of high-dollar ticket buyers who get to see the majesty of the maniacally and meticulously monitored beasts mere inches away.
Across the way, the viewing area is elevated. Multiple levels of racegoers peer over the railing to get a glimpse of their favorite horse.
I was skeptical of the updates. Shit is legendary.
All told, Churchill Downs will have spent upwards of $1.3 billion on renovations and additions since the turn of the century.
Upwards of 170,000 attend on the first Saturday in May. It’s watched by over 20 million worldwide.
Churchill has its own gaming facilities now. New on-site hotels are in the works. It’s a massive entity with accounting departments the sizes of a college football team.
Last year alone, CDI did $2.5 billion in revenue. And they are only getting started.
ONE THING REMAINS the same, though; And that’s the spirit of Derby and its surrounding events.
The race itself lasts two minutes. Two. That’s it. Shit, I watched the Masters this year for 15 hours.
But as our attention spans shrink, as we are just constantly looking for the next thing — the next crack-like dopamine rush to flood our brains — Churchill Downs and the Derby are ahead of the curve.
Churchill Downs has survived a litany of punches like hometown hero Muhammad Ali in a 12-round championship fight. It’s a testament to the resilience of the city, its residents, and those who have kept this thing going strong since the back half of the goddamn civil war.
When this thing started, most people didn’t have electricity in their homes. Now, Churchill has periods where it draws 25K to watch night racing, or “Downs after Dark”.
A festival spans three weeks leading up to the big day. A million people flock to watch one of the world’s largest fireworks displays. There’s marathons, hot air balloons, boat races, bed races, golf tournaments, parades. Enough events to damn near shut down a town for a month.
All of this, essentially, for those two minutes.
Churchill Downs has survived multiple doping scandals, animal safety concerns, racial and gender inequality concerns, recessions, viewership regressions, and kept getting up stronger each time.
No brand in sports has done that well for that long.
People rode horses to the first derby… to watch horses. They ran it at 3 PM so that everyone could get home to their electricity-less houses before dark.
Aristides ran the mile and a quarter in 2 minutes and 37 seconds. Which, yeah, that’s slow. But you’ve got to think- His Jockey, Oliver Lewis, was probably like well, that was cool, and then looked down at his mount, patted him on the neck, and said “let’s go home, boy!”
THE RACE ITSELF is one thing. If you’re from Louisville, you know well that men will sit around and talk speed figures for the first time in 51 weeks like they are some sort of savant and then get scolded on the way home for burning through the kids’ college fund and upchucking minty j’s on their shoes.
The event is another. And Thompson does well to distinguish the two from one another.
Louisville, the city, has become so much more. It’s a sports mecca. It is Louisville and Kentucky. Red and blue — on the hardwood and in its justice halls. It’s a bourbon hub. A foodie paradise. A cultural underdog. But as much as you want to separate yourself from the cheating, the scandals, the moral high and mightiness, and the drunken redneck stereotypes that make people turn their nose up at this event, you can’t. And won’t!
Kids come out of the womb around here knowing how to bet a $2 exacta box. I vividly remember the cackle of a cigar-stenched bookie at a derby party when I dropped down a one and a five and proudly proclaimed “I’ll take 2 across the board on the 9.” That horse turned out to be Silver Charm. So, yeah, I kind of know stuff, okay?
You can’t help but embrace the charm of Derby.
Maybe it’s musk of the Woodford Reserve seeping through the pores of a seersucker-clad socialite as he bumps into you on the way to the betting windows. Perhaps it’s the bloom of the… Ah, fuck it, Thompson told it way better.
Later Friday afternoon, we went out on the balcony of the press box and I tried to describe the difference between what we had seen today and what would be happening tomorrow. This was the first time I’d been to a Derby in 10 years, but before that, when I lived in Louisville, I used to go every year. Now, looking down from the press box, I pointed to the huge grassy meadow enclosed by the track. “That whole thing,” I said, “will be jammed with people; fifty thousand or so, and most of them staggering drunk. It’s a fantastic scene — thousands of people fainting, crying, copulating, trampling each other and fighting with broken whiskey bottles. We’ll have to spend some time out there, but it’s hard to move around, too many bodies.”
“Is it safe out there? Will we ever come back?”
“Sure,” I said. “We’ll just have to be careful not to step on anybody’s stomach and start a fight.” I shrugged. “Hell, this clubhouse scene right below us will be almost as bad as the infield. Thousands of raving, stumbling drunks, getting angrier and angrier as they lose more and more money. By midafternoon they’ll be guzzling mint juleps with both hands and vomiting on each other between races. The whole place will be jammed with bodies, shoulder to shoulder. It’s hard to move around. The aisles will be slick with vomit; people falling down and grabbing at your legs to keep from being stomped. Drunks pissing on themselves in the betting lines. Dropping handfuls of money and fighting to stoop over and pick it up.”
I THINK I HAVE A BEAT on what has kept this ball rolling, and will continue to do so for the next 151 years.
It’s something that other industries have leaned into ever so carefully.
Social. Media.
If there’s one place where Derby is batting .1000 its on your instagram feed. The Derby and CDI are all-in on creating an elite social footprint.
The official account posted a staggering 40 Instagram reels on Oaks Day.
I caught a glimpse of my buddy Tanner, a talented videographer whose work you’ve seen our our site before, getting shot after shot of the sites and sounds on Thursday.
My partner Jacob slowly sauntered into the paddock multiple times sporting a brand new suit and a fresh shape up, cooly holding a beer and program in the same hand. Tanner had him back up and do it again so that the lighting was just perfect. 2 hours later, Jacob panned across my phone screen for a few seconds in a promo video.
Churchill’s social presence is just the tip of the iceberg.
Any social media star who is anybody makes appearances at Derby. And it’s all about getting the shot.
Tik Tok influencers show off their outfits on Millionaire’s row and then jet for one of the hottest parties in town.
Celebrities post their gaudy wagers online and stars pose for the never-ending barrage of cameras, angling for the best shots.
This is what it’s all about.
While basketball has celebs in courtside seats, football has Taylor Swift in the Chiefs boxes, and so on, Churchill Downs has thousands of seats and elite-level views for the rich and famous.
Anyone who is, has been, or ever will be anyone is there for Derby, soaking in the scene just like Thompson did all of those years before.
That’s the magic sauce. That’s what gets you from Aristides to Zenyatta.
SATURDAY MORNING. Windows open again. Headache. Three ibuprofens down the hatch. Second cup of coffee. Back in my office seat.
In walks our seven-year-old. She’s such a butthead. I love her dearly, but when she starts one of her broken english demands with “please”, she’s up to something.
Ellie is standing in front of me ferel as ever, hair going in 40 different directions, two different colored socks. Bag of chips in hand. She’s not supposed to have food upstairs. She’s cute. I digress.
“PWEASE…”
She thought for a second and wryly smiled.
“Pwease downwoad the Twin Spiwes app. I want Jo-nolism, Gwan-de, and Chuck of Gowd.”
Grande just scratched, I regretfully inform her. That’s stupid, she says. “I have a bruise on my foot, too. See?”
Kid’s going places.
“Go ask your mom what horse she wants instead of Grande.”
I sip my coffee. This is what it’s all about.
The next generation of degenerates waiting in the wings. They’ll grow up to be something one day.
But for two minutes a year — or three weeks — They’ll do what we’ve always done.
Because it’s Derby, dammit. Whether you like it or not, it’s going stronger than ever.
