Entitled Little Bitch | At The Derby

It was a perfect day – the worst day to stand in a field inside ten furlongs of racetrack for ten hours. The barn-sized flatscreen looming over the southeast strip said the weather was mostly cloudy which implied the weatherman’s intelligence to be either artificial or very low. The only accumulation above us was the occasional wisp of chemtrail-ish strati. The sun burned high and hot. The only shade was in the shadows of the bathrooms, the smattering of barren trees, and the line of people, boiling in bourbon and printed virgin wool, waiting forty-five minutes for the privilege of withdrawing cash from an ATM with a $5 surcharge.

The Kentucky Derby of the raging twenties is no longer decadent, very depraved. You’re herded – with far less fanfare than the thoroughbreds – through towering Rent-A-Fences, metal detectors, and a cement tunnel into a large pasture with the air of a state fairground on the day the ferris wheel is due to be packed away. Post-fasch-wave. Post-(to-mid-)pandemic. It was the race where a white rapper’s DJ killed a woman in a club the night before. As such the energy was singular. Barbed wire gates with the occasional station of armed guards and military personnel surrounding the circumference gave the place the feel of a prison and/or slaughterhouse. This was compounded by the fact that my general admission ticket did not buy me the right to reenter. You can come and go as you please, so long as you don’t please to come again. I arrived at 10:30 a.m. The main event was at 6:57 p.m. I found myself wishing I had read the fine print. Particularly when I discovered the Juleps and Lilys to be $15 a piece. The hard seltzers: $12. The cheap beer: $10. The bottled water: $5. And my flask: forgotten at the tiny house I’d Airbnb’d for the weekend in the backyard of a Louisville trailer park twenty minutes out. 

The earliest arrivals had already locked down the prime real estate. Miniature picnic slash tailgate setups sprung up around every inch of unobscured track and they were not separated by six feet. We were outside. Sure. Still. It didn’t feel like it.

So I paced aimlessly. Raced from one end of the infield to the other as the horses flew by, trying to catch ten seconds of the first race instead of the requisite five. Then fell and lay in the grass as the late morning crowd trickled in. And I tried to puzzle out why I was here at all. 

The Kentucky Derby had always been on my bucket list. Sartorially, if for no other reason. Back in school, I dressed, unironically, Derby-appropriate, daily. My personality had been replaced by an interest in getting all dressed up with nowhere to go. Spending a race day infield (an event I assumed served primarily as FOMO fuel or a glorified Instagram wall for very pretty girls and very drunk men) seemed like a natural extension.

Until I grew up. Started dressing like a normal human being. All of a sudden it fell off my radar entirely. 

Then, while bingeing Hemingway, the Ken Burns documentary, the pictures of my longtime problematic favorite slash literary idol ringside at bullfights had reminded me I was washed up, stale, old at 25. What was my perspective? I wrote mostly about fear of love, fear of death, fear of life. Everything I had to say had already been said. Better. I needed something new. Bullfights, Burns said, represented the conflict at the core of the human experience. Awe. Beauty. Ritual. Routine. The end’s inevitability. I’d always admired Hemingway’s fascination with the parallels between man and nature. It all seemed so primal. The bulls. The big game. And I vaguely remembered something about horse racing?

Wonder when the Derby is? Googled it. One month. Tickets on sale tomorrow. 

I set an alarm and bought two. 

It seemed like the thing to do.

Not like I needed an excuse to buy a new hat. But I found one, the one, tucked behind the checkout line at a vintage store the night before we had to leave. It was made of straw, boater style, wrapped in a thick black ribbon with thin red and yellow stripes. They were about to close the store and I was about to leave but I stopped them and myself and asked the clerk for the price. She yelled over to another employee, who yelled back “$75?” with a question mark, like she was used to haggling. 

It’s true vintage, the employee amended. 

How old? I asked. 

Pre-fifties? she asked. 

Probably mid-thirties, the clerk said. 

Dubious, I bought it outright. 

Headed to the Derby tomorrow, I explained.

Oh, said the clerk. Good for you. I’m terrified of horses.

I wasn’t. But I couldn’t blame her. Something about horse racing felt so raw. The muscles. The money. The breaking-a-leg-and-getting-shot of it all. I was sure there’d be some magic there. At least some life to fear. 

But there I lay, in the grass, feeling nothing but the sun beneath my five-inch inseams. 

Still I couldn’t understand why. By noon, the students arrived, bringing with them the vibe of a public beach (without the ocean) meets a Gatsby party (without the pools). The air stank of fermented liver and leather wallets. The wall of outfits was so expressive, no one stood a chance at self expression. The students looked as uniform as they would have on campus, only said uniform was now primary colored pastels, secondary colored button-ups, Ray Bans, bow ties, pants printed like lake house décor, the occasional sport jacket with a sports team logo or stars and stripes plastered all over. The women wore dresses like they were trying to camouflage themselves on a Caribbean beach, walked inexplicably in heels, hid beneath an indistinguishably vibrant array of hats, a flower garden through the eyes of a small child. The faces were uniform too. Nondescript influencer beauty. Frustratingly universal fresh haircuts. Expressions like at any moment their best friend was about to appear in the crowd and welcome them to the party. 

Fucking Braaad!

I saw the same cheap boater hat at least a dozen times. I could picture the Facebook ad. True vintage. Mid-thirties style. Side by side it was indistinguishable from mine. 

The older generation sat on lawn chairs in fedoras and newsboy caps, sometimes sport shirts with inverted cuffs, sometimes tees, chewing on the tips of pencils, flipping through the program, looking for new ways to recoup their loss on the Miller Lite can in their cup holder. 

I’d had a half-baked notion of striking up a conversation with the expertest expert at the Derby. Someone who’d attended since the sixties, who could teach me the ins and outs of the animal, alien phenomenon, and I could walk away an expert myself, something new learned in a day, ready to pat my own ego for it and pass it on, as we are evolutionary encouraged to do.  

What I heard in passing (He’s an Ocala! They always do well.) did not do much to convince me such an expert existed. I did single out a few contenders though. A man sat alone by the halfway line in yellow plastic sunglasses, a camp collar shirt, and cargo shorts, leaning forward in a folding trail chair, watching the stats, not the horses. An old woman with weathered skin and a black hat giggled to herself as she circled names on a page. A blob of a human being, shirtless, hidden behind a tiki mask, rooted into a chair by the food tent, greeted us as we walked in and was still there on our way out. They all seemed far too at home to disturb. 

The few conversations I did have were initiated with me. Mostly about the hat:

Nice hat!

Thank you.

Yours too. I meant his. But yours too.

But I found, despite a growing stack of grossly overpriced souvenir cups, I was not drunk enough to properly engage. There was one topic of conversation, however, unifying everyone. 

What’s the vibe here? I asked. In one word.

Literally every conversation I’ve heard? Money.

A second dust settled on the grounds after each race: desperation. Winners reinvested in testing their luck. Losers bet riskier to make it back. And I, despite having invested exclusively in an inebriation I was not yet feeling, I felt it, too. A reserve of anxiety bubbling in my gut. Maybe left over from our cavemen days. A time when a crowd of people who look like you, desperate and wild, meant the risk of deadly outbreaks or senseless violence. 

I found the one free spot of shade on the infield. My legs by then outshined my Nantucket reds. It was under a small, spiky, unclimbable tree across from a gutter strategically placed in a beautiful field, already overflowing with beer and sauce-soaked trash. Two guys my age in panama hats and beige blazers walked past. 


Good point bro! Good point.

One of them tossed a can over his shoulder. It landed by the rest in the grass. 

Litter. Sunburns. Expensive drinks. Angst at a gambling event. Stupid things to stress.

Pick it up. Sunscreen. Get a real job. Get over it. Solutions everywhere.

I breathe, relax, text a friend:

Box seats next year. How long til we get our own? I can already see us rooting on Look-At-God and Won’t-He-Do-It.

Breathe. Relax. Think.

But how do you solve for why?

I went looking for magic, not logic, at the Kentucky Derby, the longest running sporting event in American history, the fastest two minutes in the world.

I found it, as always, in the experiences in front of me. Cuckoos flying low over the dirt. Voices rising as the dark horse found the inside track. A beautiful girl, fixated on the gate, the moment the horses rush past.

But, as always, it was caked beneath layers of ill-defined malaise, something vague and very American and impossible to unearth. Except for those rare events, when the perfect chemistry of adrenaline and boredom and overwhelmment and loneliness and mass produced liquor clears your vessels just enough for you to have one original thought, in which case…

I’ve got it, I said, and sat up suddenly. The hat fell off my face. It’s a parody of a parody of a parody. Once upon a time, someone saw horses racing in the wild and made a sport of it. Then someone saw horse racing and made it for the rich. Then someone saw the rich racing horses and made it an event in order to get richer and now 147 races later all the wild and horses and getting rich get mixed together with the liquor and the dopamine and the communal feeling of racing toward an ending and no one, not just me but no one, knows why they’re here. Or even what we are parodying.

Sure it was a strong observation, I fell back in the grass, satisfied. No one said a thing. 

The roses ran. A horse won. It was an Ocala.

The sun loomed low over the big screen. 

Below it, at the front of the line to the All Windows … Sell Or Cash booth, a man gripped the bars, screaming.

I won five thousand dollars! Give me my fucking money!

Behind the line, another man, alone in a sunbeam, spoke to the instant replay.

She road the fuck out of that horse! [Unintelligible.] Twenty. What? Twenty six bucks to win? That’ll buy dinner anyhow. Somewhere. Sushi.


She road the fuck out of them.

Broke, lost, not even drunk, I followed the familiar stadium chants echoing from the exit tunnel. On screen, the man who bought the winning horse accepted a trophy. To the side, a frat boy watched pensively, wearing the same hat as me.

I wonder how much money he made today.

A week later the horse got cancelled. Turned out to be a junky. Went on to run in the next race anyway. Who knows how these things work? Who even cares? We watch nature run its course on manmade turf. We play dress up to forget who we woke up as and remember we’re no different from anyone else. We bet on horses blindly, hoping to win money, to spend again, burnt, violent, sick, on a time we’ll never forget. 

I threw away one last profound observation before disposing myself into anonymity too:

Well. What a day.

The one next to me nodded with solemnity.

We came. We saw. We left.