The Kentucky Derby is (still) decadent and depraved

She was dressed in a deep pink, satin looking dress. Had she not been in a prone position with a glazed look in her eyes then she would have looked every inch the elegant southern belle. Her toned and tanned long legs certainly caught the eye, but they were splayed at odd angles as she lay on the ground.

Still, her stupid smile was almost angelic. As she lay there, friends – and no doubt some strangers – gathered around her to offer support. Or just to snap the picture of the fallen nymph in drink-fueled distress.

The four of us looked on with concern and a little astonishment.

We knew that things could get a little debauched at the Kentucky Derby. But it was still only Friday, more than twenty-four hours before the main event.

We were four guys who had come here from different parts of the country. Three of us were in town for our very first Derby.

Of course, we had all read Hunter S. Thompson’s defining account of the antics that used to unfold at Louisville’s Churchill Downs during Derby Week.

However, the one local of the four of us, Bill, had assured the other three that things were different now than in Hunter’s day more than fifty years ago.

“The Derby has been cleaned up a lot since then,” Bill insisted.

And he should know. The one Kentuckian of our group was born just outside Louisville and knew his horses, as well as the people that flocked to see them race. He was a veteran of at least twenty Kentucky Derbies, he said.

Above all, Bill was our most generous host and guide over a weekend that none of us would ever forget.

Friday, he told us, was our dress rehearsal. It was our curtain raiser to acclimatize us to the track and the sights and sounds we would see around it on the day itself.

The day culminated in the famous Kentucky Oaks fillies’ race, in which one of us would even pick the 4-1 winner with a hundred-dollar bet.

Bill’s father had joined us for the Oaks. A hale and hearty man of seventy-four, Bill Sr. said he had been to more than forty editions of the classic race.

It was a mind-boggling number for us three neophytes, excited as we were – like kids on Christmas Eve – for our very first Kentucky Derby.

As such a veteran, perhaps Bill Sr. had even bumped into Hunter when the latter was on his infamous drunken rampage at the 1970 event?

We hadn’t had a chance to ask before we reached the back end of Friday’s racing.

The Oaks had just finished. The tension of the day had been building for hours as punters clad in pink strutted their stuff around the track. The pink dress code was a tradition for the Oaks and the crowd did not disappoint in their sartorial efforts.

Ladies from twenty to seventy had gone the extra mile with their outfits. Concerns about exposing too much flesh to the intermittent Kentucky sunshine were pushed to one side as the male half of the throng were offered a feast for their primal senses.

An honorable mention, however, must also go to those gents – a majority in fact – who didn’t let the side down. Immaculately pressed pink suits topped with straw boaters were a common sight that Friday afternoon.

One Southern wag informed us that the gentleman’s job, from a sartorial perspective, was simply to ensure that the eye was drawn to the female form and attire. Well, there seemed no danger of eyes not traveling in that direction from what we could discern.

We had claimed our box at Churchill Downs around lunchtime, fueled by a few cheeky shots of what Bill Sr. had called “brown water”, the finest Woodford Reserve bourbon we could lay our hands on.

One of Bill’s childhood friends, Alan, had also joined us on Friday and had kindly lined up the brown water beverages for each member of the group in our hotel room, improvising with the establishment’s paper cups.

(The brown water had to sustain us for our journey from our hotel in Southern Indiana to the racecourse. More on that later.)

Once we were in our box, the one single and romantically unattached member of our group, Denton, soon became taken with two beautiful visions in pink who were seated to our left.

Denton had driven twelve hours the previous day to reach Louisville from his home in Vicksburg, Mississippi. If he was tired, however, the sight of our next-door box neighbors Tracey and Casey suddenly energized him. What is more, he wasn’t deterred by their curmudgeonly male companions.

At first glance, Tracey looked like the only slightly older sister of Casey. But after Denton had engaged the duo in conversation and introduced them to the other members of our group, it soon became apparent that Tracey was, in fact, the age-defying mom of the college-aged Casey. What is more, Tracey informed Denton that she had three other children.

Within minutes, Denton had declared to the rest of us guys that he had fallen in love with the comely Tracey. Blonde, tanned and with an especially well developed chest, Tracey was indeed striking. Nonetheless, the other, married members of our party didn’t have the same luxury that Denton did of giving his heart away so easily.

At any rate, we could see that the newly announced love of our Vicksburg-based buddy was, sadly, likely to remain unrequited. Nonetheless, none of us wanted to point this out directly to our friend while he was enjoying his day.

However, we soon learned that another gentleman nearby had been as engaged in watching the people around him as he had been following the horses on the track.

“Don’t think so,” came the slurred male voice from a location we initially couldn’t pinpoint. “Nah!”

We ignored the high-pitched noise at first.

“Worth a try though,” the voice persevered.

I followed the strange, reedy sound and saw a diminutive fellow in a full grey morning suit in the box below ours and to the right.

“What’s that pal?” said Bill

“That lady with the big bazookas is hot as hell,” the man said. “But she don’t look up for it.”

The man’s voice was so odd that it sounded as though he had ingested helium before addressing us. Helium followed by about ten straight Woodford Reserves.

Besides his strange way of speaking, the man looked like a dead ringer for one time Hollywood heart throb Richard Gere – in the grey phase of the actor’s career. Except that this was a pint-sized version. Our new friend couldn’t have been more than five foot three and a hundred and twenty pounds.

If we were worried that Denton might react negatively to this unwanted observation, then our friend soon assuaged our fears.

“You are probably right,” Denton agreed with helium man. “By the way, have you got any tips for the next race?” he asked, cleverly changing the conversation.

“Well it’s funny you should ask,” the man replied with a squeak.

Within less than an hour, Denton was counting his winnings and declaring his faith in the expertise of “helium man”.

And so our Friday wore on. We shuttled back and forth from the track to our box. The Kentucky sun came out and went back in. We won some race bets. We lost far more than we won. In between, we consumed more mint juleps and old fashioneds than we could recall, let alone count.

Occasionally, and only occasionally, did we remember to soak up the booze with a pulled pork sandwich or some hearty chicken tenders. That familiar smell of fried and barbecued food would draw us in whenever the alcohol content in our bloodstreams threatened to veer into dangerous territory.

By the time we reached the Oaks post time we were swaying but we were still in the game. Ten minutes before the race and the energy at Churchill Downs was suddenly at fever pitch. The place was primed. It was as though everything over the preceding six hours had been merely a prelude, an appetizer to be enjoyed at our leisure.

Now, here was the main event.

We would remember that pre-race feeling and the fact that we could actually recall the race itself, as well as the win with our bet, because come the Kentucky Derby twenty-four hours later some of us would barely be conscious.

Certainly, the winning horse, “Secret Oath”, was appropriately named as far as this weekend was concerned. She did us proud with her two lengths triumph.

In any event, flush with victory and with our group still standing, we dragged Denton away from Tracey and Casey, leaving our box to thread our way through the dispersing crowds of pink, back to Bill’s Chevy Suburban in the parking lot.

It was then we saw her. The fallen southern belle.

She lay prone in her pink, despite her distress somehow delighting in her predicament and drinking in the attention from bystanders.

It was clear that she had consumed many times the number of mint juleps she should have. Her feet, legs and no doubt her entire motor functioning were no longer things she could trust.

Bill, decent and – as the designated driver – the most sober of our group, offered to help. But southern belle’s friends quickly rebuffed the offer.

“Don’t worry,” one lady said to Bill with a mischievous grin. “This will be great for the gram!”

“Ok,” Bill said. “You guys have got to do you. I hope she is going to be ok.”

And with that we left the lady to her predicament, trusting that she was in the hands of friends.

Little did we know that her fall from grace was a warning for our own Derby experience to come, sprawled out there on the Churchill Downs concourse in front of us.

ROAD TO THE DERBY

Having set the scene for Saturday, it’s only right to provide a little more context.

As an Australian living for over a decade in a quaint Westchester commuter town, I had never really gotten into the American racing scene the way perhaps I should have.

I say “should have” because back in Oz I had been a fan of the horses. Not a fanatic, to be fair. But certainly partial to several visits per year to the track near my Sydney home for a flutter and a few beverages.

And, on one occasion, a few years after college, I had gotten tickets to the Melbourne Cup, the only race in my native country that can compete with the Kentucky Derby for spectacle and prestige.

Still, after many years in America, racing was a long way from my thoughts.

That was until early March this year when I bumped into my friend Austin at a child’s birthday party that our four-year-old daughters were both attending.

Austin is a good man, a son of the American South transplanted to suburban New York, and a successful banker at one the most prestigious institutions in the country. We had quickly bonded as fathers whose kids were in the same school and with wives who were also friends that liked to go thrift shopping together.

At that kids party, as yet another round of soggy pizza and pink sponge cake was passed around, Austin hit me with it.

“There’s a group of us going to the Kentucky Derby in May,” he said. “Do you fancy coming?”

I didn’t say yes straight away even though I felt like it. I tried to take my time to process it.

“It’s definitely a bucket list item,” Austin explained.

But I didn’t need any more persuading. Within a couple of days I had accepted his invitation and I was admitted to the Derby group.

Two weeks later, through the miracle of Zoom, I met Denton, a bearded Southern gentleman and entrepreneur from Vicksburg, Mississippi; and Bill, a larger-than-life commercial banker from Kentucky with a heart of gold.

Some more fun zooms and dozens of texts later we had settled on colorful outfits for Derby weekend and an itinerary.

ARRIVAL

Austin and I had had to fly into Cincinnati Airport. So scarce were flights to Louisville by the time we had got around to booking.

Still, although we were flying into a place some ninety odd miles from downtown Louisville, there were numerous large hat boxes being stowed in the cabin by our fellow passengers, betraying their ultimate destination.

“I know where you are going!” the flight attendant said with a knowing smile and a wink to the couple seated in front of me who were lugging just such a box.

We arrived to an overcast early evening with scattered rays of sunshine trying to punch holes of light through the gloom.

As we exited the terminal building I saw arriving passengers being greeted by local friends.

“Great to see you!”

“How the hell are you?”

“I am excited for the race. Mo Donegal is nailed on to win.”

“No, Epicenter is a certainty!”

And so the banter went on until Austin spotted Bill, who had very generously come to the airport to pick us up.

“They are all going to love your accent,” Bill informed me. “There’s no danger of them thinking you are from Kentucky. But remember it isn’t Australia here, or even New York, which you are used to.”

We hit it off instantly as the three of us bantered all the way through the drive to a small town just outside Louisville.

Bill had booked us a table at a picturesque restaurant on the Ohio river. Denton, straight off his own marathon twelve-hour drive from Mississippi, met us there and we settled down at an outside table to plot our weekend.

Denton, it turned out, was Austin’s fraternity brother from their days at Ole Miss together. They had experienced nearly two decades of fun and malarkey in each other’s company, as Denton’s stories – sometimes to Austin’s discomfort – would reveal throughout the ensuing two days. Bill, meanwhile, had been a colleague of Austin’s from their time working at an Alabama bank together.

The three other guys clearly had a strong bond from shared experiences and much cultural ground in common.

For the first few minutes I did think about how I, not even a Yankee, but an Australian from the other side of the world, would fit in.

But I needn’t have worried.

After the first couple of glasses of brown water, I too was quickly bonded with the boys. They seemed to appreciate the outside perspective that I brought to the table, and I was beginning to relax, understand their sense of humor and very much enjoy their company.

Bill had secured us accommodation at a hotel and casino in Southern Indiana, some twenty miles from Churchill Downs on the other side of the Ohio River. To get there from Louisville we had had to take the I-64 over the famous Sherman Minton Bridge.

The double-deck arch bridge was over sixty years old, and it showed. Much of it was covered in red rust and certain sections appeared to be held together with floaty white tarp that might as well have been fixed onto the bridge’s structure with bubble gum.

Most worryingly of all, the bridge appeared to wobble each time we crossed. If there was a poster child for the need for Joe Biden’s one trillion-dollar infrastructure program, then this would be it. We hoped it was on the shortlist for assistance. Still, it did carry us safely as we shuttled back and forth across it multiple times throughout the weekend.

DERBY DAY

Having survived Friday, the day of the main event arrived with a weather forecast that Bill said was perfect. Conditions would be dry, somewhat overcast, and cool enough in the mid-sixties. We would neither melt in the Kentucky sunshine nor drown in a deluge of warm precipitation.

Getting dressed in the hotel room it was time for a final review of our attire. By far the most striking of the group was Austin. His green seersucker suit and bow tie earned him the instant nickname of “Spearmint Rhino”.

Meanwhile, Denton – despite the misgivings of the other guys – insisted on a pair of red-striped shorts with an orange jacket. It wasn’t textbook but it somehow worked. I had opted for a more sober light blue jacket, mint-grey slacks and a straw boater. Bill, the old Derby hand, was content with his banker’s pinstripe and a neutral shirt.

Arriving in the hotel lobby we soon realized that we would have a lot of competition on the fashion front. It was packed with our fellow racegoers, many of whom were sporting the most magnificent Derby outfits. In particular, the ladies’ hats with large flowers caught the eye.

We got to Churchill Downs around noon, a respectable time given that a couple of our number had engaged in an Oaks afterparty in the casino bar until the wee hours. As we approached the racecourse it seemed that almost every house in the vicinity was offering its front yard as a parking space for spectators. Residents held up makeshift cardboard signs indicating the prices they were charging. From what we could see, there were plenty of drivers taking them up on their offers.

One house, literally a stone’s throw from the course entrance, had a slightly different and even more enterprising offer. The residence had a swimming pool in its backyard and a large cardboard sign on the front porch announced a, “Kentucky Derby pool party after the race – $50 per person with a free hot dog”.

We didn’t think we would end up at that particular after party. But then we couldn’t know then exactly where the day would take us.

As we entered Churchill Downs it was clear that the energy of the place had already ratcheted up several notches beyond the previous day. The outfits were bigger and bolder. The hats and accessories were way more outlandish.

And the crowd seemed twice as big.

By post time just before 7pm, there would be more than 150,000 souls, including a former US President, packed into the famous old venue.

Before we took our seats, we stopped by the red carpet that the venue had set up for racegoers to gawp at arriving celebrities. TV cameras, press photographers and casual observers like us were crammed in against the barrier to see whom we could spot.

There was a procession of middling celebs: TV actors, retired Nascar drivers, fashion influencers from cable shows and one young NFL quarterback. I did not recognize many of them, so it was helpful that they were accompanied by members of the Churchill Downs staff carrying their names on placards.

I spotted a couple of young women standing next to me googling each name as it was brought forward. They didn’t know these celebs any more than I did but they were on the red carpet. That was good enough.

Then there was a buzz at an altogether different level. An impeccably groomed man with a striking blonde woman by his side and two children in tow moved to the middle of the red carpet.

“That’s the governor of Kentucky,” Bill informed us.

The governor certainly moved as though he was in charge. He didn’t rush through the red carpet like the other celebs. Instead, he and his family held their ground in the middle of the spectacle for at least twenty minutes as he gave numerous short interviews to the TV cameras and other members of the media.

The governor seemed to be handling most questions with ease. Finally, however, he seemed to be caught out by one.

“Who is going to win today,” a reporter from a national sports channel shouted out.

All heads briefly turned to the man who had asked the question. Then they turned back again to the governor. For an instant he looked lost for words. Then he regained his composure and a smile spread across his face.

“I think I have a pretty good idea about that,” he said. “But I am going to keep it to myself if you don’t mind.”

INFIELD

The celebrities on the red carpet would be enjoying their parties in private suites high up in the grandstand. There, they would be rubbing shoulders with billionaires, multi-millionaires and the local political elites.

The lower clubhouses at Churchill Downs, where our group was, accommodated the merely reasonably well-to-do. It was still a salubrious experience with an open bar, food service and polite conversation.

However, to many, the authentic Derby experience was the infamous infield – the large grassy area enclosed by the one and one quarter mile track.

Having had our fill of celeb spotting and having placed our first few bets, we were ready to see the infield party with our own eyes.

To reach it we had to go through a long concrete tunnel under the racecourse. On the other side of the tunnel was a security checkpoint set up to prevent “infielders” from getting into the nice part of the course. The security men checked our red wrist bands and let us through into the unknown.

“Good luck,” one muttered. “Are you guys sure you want to go in there?”

We had heard the stories of the wild goings on in this infield compound. Mud wrestling, drinking contests and public sex.

But we had to see it with our own eyes.

Before leaving the clubhouse we had each grabbed at least two mint juleps from the open bar so we hoped we would have refreshments for a little while at least.

The most striking thing at first was the age difference between this place and the clubhouse.

Most infielders were college kids.

“It looks like a tailgate at an SEC game,” Austin observed.

The second obvious thing was how rough an experience it was compared to that enjoyed by the well-heeled punters on the other side of the tunnel. Lines stretched dozens of people back for every conceivable need.

For instance, people thronged around a tiny number of ATMs, an absolute necessity for the cash-only food, drink and betting concessions.

“Not very smart to come to the infield without any cash,” one older guy observed sardonically around the ATM lines.

Assuming you could get some cash, there were then lines just as long awaiting you at the drinks and food stands, where you might pay as much as twenty dollars for a no doubt lightly poured mint julep.

Some rain on Friday had left the ground a little muddy although not as bad as we had feared. At 4pm, around three hours before post time, people were crammed in. There was barely a square foot of soggy turf unoccupied by human feet. What is more, across most of the infield there was zero visibility of the racing itself.

Yet, the less than perfect conditions didn’t seem to dampen the spirits of the thousands of infielders. They were clearly having a ball.

A drunken man, perhaps in his early thirties, staggered towards us.

“I want to find a woman to make out with,” he declared.

He didn’t need to wait long for a response. Before we could reply, a young lady, who had overheard him, tapped him on the shoulder.

She seemed a little glassy eyed but not quite as worse for wear as the gentleman.

“I won’t make out with you but I’m happy to chat to you,” she said, to our astonishment. “Then we can see where it leads!”

The inebriated man, whose beige suit was covered in muddy stains, gave us a wink and a smile, then turned to the young lady.

“Good to meet you,” he said. “My name is Phil.”

“I’m Mindy,” the woman said.

We watched for a minute or two as Phil and Mindy conversed in front of us. Then, they trudged away with Phil’s arm around Mindy’s waist.

Perhaps she would soon change her mind about the make out.

We explored the area for at least another hour, and observed numerous Phils and Mindys in various phases of courtship. Some phases far too graphic to describe to a polite readership.

At any rate, it was Austin who called time on our anthropological expedition.

“Right fellas, time to return to civilization!”

We all agreed. Besides, we had an important race to see, and we certainly weren’t going to follow it from that muddy pit.

THE RACE

In the days that followed we could barely recall leaving the infield, let alone stumbling back across the tunnel to the more respectable part of Churchill Downs.

I can now vaguely recall our group grabbing another several rounds of drinks from the open bar before placing our final bets for the big one.

Mo Donegal featured prominently in our thinking, although favorites Epicenter and Zandon also found their way onto the tickets of at least two of us.

In any event, the four of us somehow made it to a prime spot at the track, a stone’s throw from the winning post.

By now, three of us, with the honorable exception of Bill (who was again our designated driver) were seriously unsteady on our feet. An uncountable number of drinks from an open bar will do that to you.

Thankfully, we weren’t alone. There were many others barely clinging on to their balance as Derby post time approached.

A large man in front of us wore a blue seersucker suit and a giant hat with a horse ontop of it. In one hand he was clutching a whole load of betting tickets. In the other, of course, he had a drink. He seemed almost more or less out of touch with his motor functioning as he swayed from side to side.

Then, suddenly, the Derby was underway. As the incredible race unfolded, he man in front of us finally lost contact with his senses completely. Just as the 80-1 outsider Rich Strike made his move, blue seersucker hat man let out a scream, threw his betting papers in the air, and toppled backwards like a tree that had just been felled in the forest.

I can scarcely recall him crashing into Austin and me.

Then everything went black.

Sunday morning, I awoke to find myself in bed back in Southern Indiana.

I quickly checked for any obvious damage and found some unexplained cuts on my hands and a bruise on my forearm.

What the hell had happened?

I didn’t have much time to ponder that question before a fully dressed Denton appeared at the foot of my bed.

“Gotta hit the road before the hangover kicks in,” he muttered, stretching out his hand for a final handshake. Of Bill and Austin, there was no sign.

I glanced at the hotel alarm clock. It was not yet 8am.

As Denton headed for the door, he turned one last time.

“Same time, same place next year?”