The Kentucky Derby: Decadent, Depraved . . . and Powerful.


Until very recently, the extent of my Kentucky Derby knowledge and experience came from two sources: (1) the insane multi-sport attention span I had from ages 11 through 18 when I followed EVERYTHING; and (2) Hunter S. Thompson. 

Between 1984 and 1991 I could not only tell you everything you wanted to know about baseball, football, basketball and hockey, but I could tell you the top five to ten contenders in multiple boxing weight classes, the top 15 tennis players, men’s and women’s, the top 15 or so golfers, men’s and women’s and, like every boy should, I could tell you who the Triple Crown favorites were most years.

I remember Devil’s Bag bowing out in 1984, clearing the way for Swale. I remember Swale dying after winning the Belmont. I remember Willie Shoemaker’s shocking win on Ferdinand. I remember the runup to all the winners from Spend-a-Buck through Strike the Gold, and even though girls and college and things caused me to drift away from it all somewhat, I still paid fairly close attention until around the time of Silver Charm. It was only then that adult life totally took over, I stopped obsessing on sports apart from baseball and I totally lost track of what was happening in horse racing apart from those odd moments when it crossed into mainstream news.

As for Thompson, “The Kentucky Derby is Decadent and Depraved” tells one very little about horse racing, but my understanding of Gonzo Journalism is such that I knew that already. It’s enough that it has always served as an influence for my writing. Indeed, as anyone who reads my stuff fairly closely knows, I am less a baseball writer than I am a writer around baseball. Thompson had his mace and amyl nitrate through which to filter his McGuffin, I have my own less-toxic biases and influences to filter baseball into my day-to-day life.

The upshot here: anything I felt or knew about the Kentucky Derby as of last week was either 20 years out of date or simply beside the point. Which turned out to be a pretty great way to approach the Kentucky Derby in real life.

Allison and her dad mentioned that they wanted to go someday, so a month or two ago I asked my guy at NBC if he could get me Derby tickets. I assumed the wait list was long and I was pretty far down the totem pole, so I didn’t bother asking for tickets to this year’s race. Instead, I asked for 2015 tickets, thinking getting in a year early would make up for me not being too terribly important in the grand scheme of things. I’d send the two of them off on a fun adventure next spring and I’d stay back at whatever house, hotel or hostel we could find to mix drinks and grill meat.  “Sure, I can put you down,” my guy at NBC said. “I appreciate the advanced notice. I’ll let you know.” That was nice of him, I thought. Being on a list this early is probably a good thing and, over the course of a year, I could properly plan a proper Derby trip.

Last Tuesday my guy’s assistant emailed me and asked where he could overnight my tickets. For this year’s Derby. “Oh, and do you plan on attending the Oaks on Friday too?” You obviously don’t say no to that. So with very little lead time, a Derby trip had to be planned. It was too short notice for Allison’s dad to make it up here from Texas, so I was going. I figured I’d go as either that 15-year-old kid who followed all the sports or as Hunter S. Thompson, which meant staying wherever I could crash and wearing whatever I already had. I was only half right about that.

Allison decided that we were going to do this right-proper. There would be hats. There would be seersucker. There would be buck oxfords. There would be bow ties. While skeptical at first, my closet clotheshorse tendencies came to the fore and, after a frantic Wednesday night shopping spree I was supplied with all of the essentials courtesy of Ted Baker, Hugo Boss and my increasingly burdened credit line.



With clothing sorted, I looked for lodging. My past trips to Louisville have taken me to the Brown, the Seelbach and the 21C Museum hotels. Those were obviously out of play mere days before the Derby – hell, the Holliday Inn Express out by the fairgrounds was going for over $600 a night by then – so I tried my luck with Airbnb. It proved to be a godsend:


Kristen and Mark own this small but adorable Urban Farmhouse near the University of Louisville and not too far from Churchill Downs. They rent out two rooms and we took one. A couple of days before the Derby it was going for what you’d gladly pay for an above-average hotel on any normal weekend. Of course on any normal weekend their room would be an absolute steal. As someone who has fallen in love with Louisville over the course of his three or four brief trips there, I will certainly be going back. And I will certainly make a point to stay with Kristen and Mark again, as the location, vibe and price are all perfect. If you need any other support for this, know that (a) they have two cats; (b) they have chickens in the back yard; and © they leave half-pint bottles of Bulleit bourbon on the nightstand for their guests.


With clothes and accommodations settled, we headed down to Louisville on Friday morning and made it into town by 1pm. While the house was less than two miles to Churchill Downs, those final two miles are the most difficult to navigate. Rather than drive and try to park several hours after the track opened and the available lots presumably full, we went with an Uber car, which got us pretty close to the main entrance of the Downs for a slightly inflated but less than usurious price. Leaving that evening was an adventure – no Uber cars could come close to the Downs and the cab line was overrun – so we ended up walking all the way back to the house, which wasn’t a load of fun. On Derby Day we got off a bit earlier, so we took our chances parking in the front yard of one of those guys who hold the signs up advertising $15-20 parking along 3rd Street, the closer to Central Avenue the better. Maybe it’s his house? Maybe the car will be there when we come back later that evening, full of mint juleps and regret? Either way, it seems like a good idea at the time.

On Friday we made the track by 2pm and caught the last four or five races of Kentucky Oaks day. Which, while advertised as a lower-key, locals-friendly day is still pretty much close to bedlam. At least insofar as bedlam can be measured in ridiculous hats, impossibly flashy clothes and rampant drunkenness. Put differently: it was wonderful. I bet on several horses based on nothing more than names – there was a minor prog rock theme, with a jockey named “Mike Rutherford” in one race and a horse with a name which included “Journey” in another – but that didn’t work out too well for me. Allison, who rides horses and has been around them all her life, had much better luck. She knows what to look for at the paddock (wrapped legs bad; shitting on the shoes of the drunk sister of the friend of the owner’s daughter taking selfies with her equally drunk girlfriend: good). She knows many of the trainers, sires and dams. Ultimately you’re still gambling, but a little bit of knowledge does go a long way.

Thing is, there isn’t much knowledge floating around. While walking to and from the paddock, to and from the wagering windows and too and from the bar I overheard all manner of systems and superstition espoused from people who, I assume, are not rich. Wait, they are all rich. It’s just that they got rich via daddy’s used car dealership or part ownership in a dubious real estate concern, not via betting on horses. I listened to their bullshit, choked on their cigar smoke and did my best to keep my fresh new bucks from getting sloshed with the bourbon they clearly did not appreciate, but rarely did I hear any true gambling insight. For the rest of day and all through Saturday I decided that all bets I placed would be based on either my own gut feeling or whatever bits of wisdom Allison had about the horse, the jockey, the owner or whatever equestrian juju she was communicating with, because at least I can begin to understand that. I bet on horses with baseball-related names. I bet on a horse with a woman jockey because that felt right. I bet on a couple of favorites because I believe in the idea of exceptionalism and the wisdom of crowds. I tended to win when I bet on favorites and lose when I bet with my gut. But I didn’t regret any of my bets, mostly because they were all pretty small.

Indeed, I’m not a gambler. I just don’t have the temperament. I’m much more interested in feeling moments and capturing the zeitgeist, so far more of my time spent at Churchill Downs was spent soaking it in and, potentially, fighting it off, Hunter S. Thompson-style, with a can of mace and my inherent skepticism of and hostility to privileged elites. The mace wasn’t necessary, but I did come away with some very mixed feelings about the overall scene.

One thing Thompson got right was the decadent depravity of it all. Most people you encounter at the Kentucky Derby are drunk and most people – at least where we were in the Clubhouse – embodied a decadence of a sort. I didn’t have some strong and overwhelming feeling of the sort of class consciousness that made Thompson so paranoid when I was there, possibly because I don’t deny that in many respects I am of that decadent class. I mean, I’m not rich or part of some real or imagined gentry, but I am white, I am a professional of a sort, I was there on a privileged lark and I don’t worry where my next meal is coming from. However that breaks down, I did have a general uneasiness at times about how natural it all seemed for all of us to be walking the line between dressing up and Jim Crow-era cosplay, between celebration of an old tradition and playacting as if the tradition was something more than historically quaint. As if our holding the door for the ladies, sipping our cocktails on a sunny southern afternoon and singing “My Old Kentucky Home” as grooms led horses to the starting gate for our entertainment and sporting wagers was anything but a crazy anachronism in the early stages of the damn nigh apocalyptic 21st century.

But you force yourself to forget all of that. At least you do if you wish to have a lick of fun and not have every person within three or four Clubhouse boxes on either side of you treat you like a leper. At least I forced myself to, resolving whatever social dissonance remained with the certainty that only bourbon can provide. And it was a satisfying resolution, as I managed to spend the bulk of my two days at the Derby in that wonderful zone north of happy but south of sloppy, my faculties always being with me but my uneasiness almost always at bay. Once I stopped worrying and learned to love the Derby I was pretty much OK. 

I was even more OK as we left the track on Saturday evening. Dodging the bulk of the crowd that filed down Central, we cut through the mostly black neighborhood surrounding Burton, Heywood, Lillian and Rodman. Nearly every yard had a barbecue going and every front porch featured music blasting. At the sidewalk near most houses were kids with coolers selling bottles of water and sodas and their parents or older siblings selling beers. Some sold dollar bin flipflops for $10 to ladies who had spent the day balancing on painful high heels and would do anything they could for relief. For $5 or $10 you could join their party, partake in the wonderful-smelling food and get comfortable.

On some level, yes, it’s mere opportunism. Drunk Derby goers in their ridiculous clothes are easy marks and are easily relieved of the $10s and $20s left in their wallets. But if you drop your cynicism and just watch the parties unfold, you see that everyone is enjoying themselves with little thought of the circumstances which brought them all together. It’d be naive and pat to say that some lesson can be learned from all of that, but it’s worth acknowledging that, on some level, a lively party, however temporary, can make up for a lot of problems and mask a lot of ugliness.



For our part, we bypassed the parties and made out way back to the car and back to the Urban Farmhouse. A quiet dinner and a quiet evening with that handle of Bulleit and a book. The next morning we work up and got some coffee before leaving town. As we left the cafe, a cop was giving a blue-blazer and seersucker pants-wearing young man a field sobriety test on the corner of Atwood and Preston. He failed and was led away in handcuffs. It was 8AM. Must’ve been some night.

I over-think most things and I’m sure I’ve over-thought my first Kentucky Derby experience. But lest you think such over-thinking prevented my enjoyment of it all, know that I had a fantastic time. I’ll certainly go again if my man at NBC can make that happen. I’ll stay at the Urban Farmhouse and drink my bourbon and my juleps and make bad bets and watch bad people – and a lot of good ones – make total asses of themselves.

And I’ll do my best to remember that just because something is a tradition doesn’t make it righteous. And just because something is less-than-righteous doesn’t diminish the power of its tradition.

(All photos were mine, with the exception of (a) the pic of Kristen and Mark, which was nicked from Airbnb; and (b) the photo of the delicious-looking meat, which was taken by Patrick Janelle and posted to his Instagram. Patrick and his friend were staying in the other room of the Urban Farmhouse and it was a pleasure to make their acquaintance. Give his Instagram a follow. It’s quite excellent). 

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at He lives in New Albany, Ohio with his wife, two kids, and many cats.

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