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My 2016 Kentucky Derby Experience Was Glorious, Drunken, And Ridiculous

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My first memory of horse racing comes from when I was eight years old. My family and I were huddled closely around our camper’s 12-inch analog television in an attempt to peer through the fuzziness and watch my uncle’s horse, Talk Is Money, run in the 2001 Kentucky Derby. Looking back on it, the dichotomy between the two situations is pretty great. My uncle was in a box seat smoking expensive cigars, downing top-shelf mint juleps, and getting ready to cheer his horse on to what would hopefully be a portion of the $1,112,000 purse. I was on vacation with my family in a rainy Florida campground with a garbage bag in tow after contracting food poisoning from a Philly cheesesteak and vomiting my guts out in the Mote Aquarium, on the beach, and the entire way back to our camper. But while my mouth may’ve been over my plastic puke receptacle, my eyes were glued to the screen.

After acting up before the race (something he’d done in the past as well), my uncle’s horse actually started off pretty well. From the 11th post position he was sitting at 7th going into the clubhouse turn. Not too bad considering the opening half mile of the 2001 race was, at that time, the fastest in Derby history at 44.8 seconds. Things didn’t end great, though.

talk crop

Image via YouTube

Technically he didn’t finish in last, because technically he didn’t finish the race. Still hasn’t to this day. Pretty impressive, if you ask me. I think less horses have done that than have actually won the Kentucky Derby, so I’m still proud of ol’ Talk Is Money (who, at 18 years old, is still alive and kicking).

Sadly, my uncle never did have another horse run in the Derby. Like most Americans, however, I continued to watch the race, along with the Belmont and Preakness, every year. So, when I had the opportunity to stay with some fraternity brothers who live in Kentucky and go to this year’s Kentucky Derby, I jumped on that shit. It was one of the best decisions I’ve made in a long, long time, and I got some of my new favorite stories ever from the trip. Here is my 2016 Kentucky Derby recap.

After a brutal 5:15 a.m. flight out of Austin, I landed in Northern Kentucky around 10:45 a.m. My Eastern European fraternity brother Goran picked me up at the airport and we set off for Frankfort, KY, where we met three more of my fraternity brothers, Gary, Peter, and Boo, for a tour of the Buffalo Trace Distillery. It took less than three hours after my plane touched down for brother Gary to have me crying laughing mid-tour by recounting the story of one of his latest sexual rendezvous.

The story goes that when Gary was out at the bars, he offered to buy a girl a shot of tequila. She refused, claiming she drank so much tequila over spring break that there was a 100% chance she’d yak if the Mexican devil’s mouthwash touched her lips. After playfully insulting her, he ended up buying her a different drink, schmoozing her tits off, and hooking up with her that night. The next morning, she sent him the following text.

Screen Shot 2016-05-10 at 3.23.24 PM

Pretty promising, eh? She had fun and she wants to do it again? He usually only lands himself in situations where just he has fun and neither of them wants to do it again, so this was huge for Gary. Despite Gary’s admission that he did not show her a very good time at all, this text seems to tell otherwise. Gary, who was now counting down the hours until their next hookup, decided to respond to her text like so.


That video he linked to? The music video for “Mas Tequila” by Sammy Hagar & The Wabos.

A pretty obscure reference, sure, but it definitely played in this situation, as Gary is telling her she needs to listen to this song to get herself in the mood to start drinking tequila again.

At least, that’s what he thought he was telling her. In his haste to get the text sent, however, Gary accidentally clicked on an ad that played before “Mas Tequila” and unknowingly copied the ad’s URL instead of the music video’s. Type the URL Gary actually sent this chick into your browser and you’ll see that this is the too-good-to-be-true video that results.

(Apparently the video has since been removed, but it was a commercial for Red Lobster’s Lobsterfest)

A fucking Lobsterfest commercial. My favorite part about this whole mixup is how he sent her the same link twice, solidifying, in her eyes, the notion that he actually meant to send her this Lobsterfest commercial. Priceless. She never responded, and they haven’t spoken since.

After the distillery tour, we headed off to grab some barbecue before heading back to Lexington, the location of the house at which we were staying. At the restaurant, I decided that we should play a stupid, weekend-long variation of credit card roulette. In this variation, we’d put our credit cards together at each t-shirt-selling establishment we go to and whoever’s card gets drawn has to buy a t-shirt, regardless of whether or not they actually want one. Then Gary had the idea that would change the credit card roulette game forever. His “a-ha!” moment? That, rather than the loser having to buy himself a shirt, he has to buy all of the winners a shirt — leaving the loser shirtless and out a decent chunk of change. The kicker? The winners are to pick the shirt that they have the smallest chance of ever actually wearing, just as a little added “fuck you” to the loser. So devious. So conniving. I loved it. Partly because I came out a winner in round one after Gary fell victim to his own invention.


It’s a great game. I highly recommend.

After t-shirt roulette, we went back, changed, and headed off to go gamble on the Kentucky Oaks at a watch party that was being held at Keeneland in Lexington. This was my first time ever betting on horse racing, which quickly became apparent to the group after I bet against myself in the first race. In my defense, a bet against me is generally very sound (click here if you don’t believe me). The fact that neither of the two horses I chose to win supports that argument, too.

That night we went out to a brewery in Lexington, where Peter fell victim to round two of t-shirt roulette.


In classy fashion, Peter ended up buying himself a t-shirt as well. Love that “in for a penny, in for a pound” attitude of his. That’s how t-shirt roulette is meant to be played. Sadly, due to drunken forgetfulness and time restraints, this ended up being the last round of t-shirt roulette played all weekend. I was on such a tear, too. If you ever see me out and would like to challenge my undefeated lifetime record, go ahead. It won’t end well for you. After some more time at the bars, we ended up A-barring back at the house, which is where the weekend’s biggest semishap would occur.

1. Short for “semi-mishap;” used to represent an event of which it would suck to be the victim, but to which it is hilarious to play witness and/or talk about.
Used in a sentence: Huge semishap at the house yesterday. Mikey was porking a lardo on his top bunk when the weight caused all the support beams to simultaneously give out. The mattress fell and completely crushed Napalm, who was on the bottom bunk jerkin’ it to the sex sounds. It was hilarious, all the beams just snapped at once. It looked like a controlled demolition of a suspension bridge or some shit. Anyways, Napalm’s in the hospital and Mikey’s gonna have to pay his medical bills.

Brother Goran distinctly told me that I could not sleep on his bed with him Friday night, which meant that I made it my goal to sleep there by any means necessary. After losing a strength-requisite door closing battle with Goran (no surprises there), I needed to devise a plan to get him to open up so I could cuddle with like he used to cuddle with his favorite goat Doncho back in his homeland.

I noticed that Brother Ben, a certified wild card, was in the process of drunkenly heating up pizza rolls in the nearby kitchen. Knowing that Goran would believe it if I said that Ben was about to kick his door down, because it’s entirely something he’d do, I started yelling “Oh my God, Ben’s about to kick your door down! 3…2…1…” hoping he’d bite. No luck — Goran didn’t open the door up. But what did happen was that I had unintentionally incepted drunk Ben into thinking he actually was going to kick the door down. So he ditched his pizza rolls and walked over to the door.

Knowing full well what he was about to do, I let out a reserved-but-sincere “don’t do it, dude.” My warning seemed to work, at least a little — he was yet to go full Kool-Aid Man on the door. That is, until Brother Jay viciously and cacophonously yelled “DO IT!”

Screen Shot 2016-05-10 at 6.13.00 PM

He did it. Jay and I immediately made a bee-line for Jay’s room, knowing full well we were at some level of culpability for what just happened. That’s not to say we were, and are to blame — we’re merely at minor amounts of fault. Sure, it was a combination of my and Jay’s actions that led to Ben one-hole punching Goran’s door like he belongs in a third grade classroom’s arts and crafts closet, but we’re not the ones who actually did it, so it’s chill. I guess what I’m trying to say is that Jay and I aren’t chipping in to help you pay for the new door, Ben.

After getting fewer hours of sleep than was probably advisable given the following day’s events, we woke up, grabbed our shit, and headed over to the bus that was going to take us to and from Churchill Downs in Louisville. After Ben got iced at the bus stop (which might have been in bad taste considering it was outside of a church), we boarded for the Derbs. Aside from some pregaming, not too much happened on the bus ride except Ben sparked up a conversation with a University of Kentucky senior whose graduation was the next day. Remember her for later.

We get out of the bus to find that we lucked into an impeccable tailgate spot in a grassy area next to the bus lot that was less than a half mile from the track. The highlights of the tailgate were:

∙When a fraternity brother of mine and his friend got into a bidding war to see who could donate the most money to the little league team that was walking around asking for donations (I think they both ended up out over 40 bucks).

∙When I took a dump in a nearby port-a-potty. Nothing has ever been more of the move. Tailgate dumps are heaven.

∙Eleven different people got Iced (we didn’t bring it back, it never left).

Now, for the part of this column where I actually tell you about the Kentucky Derby itself. Our plan was to get into Churchill Downs around 3:00 p.m., but it ended up being a lot closer to 4 p.m. Seeing as the post time for the Derby was around 6:55 p.m., that only gave us around three hours of being inside the Derby grounds. The tailgate was a blast and all, but next time I think it would behoove me (pun intended) to get in a bit earlier and take in some more of the atmosphere.

The atmosphere: electric. Smile-inducing. Just plain fun. I’m not sure I’ve ever seen a group of people in such a good mood. What’s not to be happy about? Booze, food, ponies, gambling, cigars — it’s every red-blooded American’s wet dream. The biggest thing I learned from my first trip to the Derby is that the Kentucky Derby is not a sporting event; it’s an atmosphere event. You aren’t there to see horses race, you’re there to be around horses racing. It sounds weird, but it makes sense if you’ve been. I went the peasant route and had infield tickets, which is another reason I’m angry I didn’t come inside sooner — the infield is essentially just a humongous tailgate inside the track. Sure, the drinks are a little expensive ($11 for a 12 oz. mint julep), but booze is super easy to sneak in and you get to watch the races while you drink instead of just straight drinking.

Infield is definitely the move when it comes to maximum boozing, but it is most certainly not the move when it comes to placing bets. The infield’s betting booths are dreadfully understaffed, which leads to obnoxiously long lines and rampant line-cutting. Why would they be understaffed during the busiest betting day of the year, you ask? Beats me. All they have to do is pay some Kentucky bumpkin $8.50 an hour to press buttons and they’d rake in tens of thousands of extra dollars. It got to a point where I was waiting so long that all I wanted in the world was for them to just take my money. I wouldn’t have even cared if all my bets lost (which they ended up doing) or if that money went right into Cletus’ “buy my wife/daughter a new ring for her sixth toe” fund, I just wanted to stop waiting in fucking line. Either download the TwinSpires betting app to place bets or do it before you get into the infield. I wasted one of my three hours at the Derby waiting in line to bet, and I don’t want one of you to make the same mistake. Actually, fuck it — I kind of do. I don’t even know any of you. Feel my pain. Fuck you.

As far as actually taking in the live event goes, I literally only caught 2 half-second glimpses of horses running, and I had to jump up and down twice and look over the infield crowd to even catch those. I wasn’t at the Derby to see horse racing, like I said earlier, but I do wish I had seen a little but more of it with my own eyes. The big screen in the outfield is way better than that old 12-inch analog, but I imagine the real thing would’ve been even better.

After the Derby, I told my fraternity brothers I’d meet them back at the bus and stayed in the infield to hang out with some college friends until around 7:40 or so. I’d been told the bus was leaving at 8:00 p.m., but figured an 8:05 p.m. arrival time or so wouldn’t be a problem, right?

Here’s a text conversation between Jay (blue) and another fraternity brother (grey) I would end up seeing the following morning that tells a different story.

Screen Shot 2016-05-10 at 10.17.10 PM

God I love my friends.

I think one of the best things about being a writer is that I don’t sweat life’s little problems. After I realized that anything amazing, unfortunate, disgusting, awful, or cruel that happens to me can be turned into beautiful, succulent content, I just stopped giving a fuck. Get embarrassed by a sorority sophomore year? Guess I’ll write about it. Jump into a trash can and have some random dude push it over? Guess I’ll write about it. Que sera, sera.

So I didn’t really care that much that I was stranded in Louisville, over 75 miles away from the house at which I was staying. It wasn’t ideal, but it was content.

But then, just as I was about to give up looking, I saw a bus stopped in traffic on a nearby city street that looked familiar. I casually walked over (acting like you’re in a hurry in any circumstance (except to catch your nut) is NF), saw it was the same driver, knocked on the door, and boarded. My arrival was met with boisterous cheers from my group, a handle of bourbon shoved in my face, and an ice cold beer handed to me, all before I could even sit down. Almost missing the bus is an experience that’s much worse content than its alternative, but a much better memory.

If you only came here for Kentucky Derby shit, you can click out now. But if you came here to read those stories I told you about earlier, here they are.


Remember that University of Kentucky bus girl Ben was talking to on the way to Louisville that I told you to remember? Gary completely cockshifted her on the bus ride back to Lexington.

1. When you cockblock your friend while simultaneously stealing his girl.
Used in a sentence: Huge cockshift at the house yesterday. Mikey was porking a lardo on his top bunk when the weight caused all the support beams to simultaneously give out. The mattress fell and completely crushed Napalm, who was on the bottom bunk jerkin’ it to the sex sounds. It was hilarious, all the beams just snapped at once. It looked like a controlled demolition of a suspension bridge or some shit. Anyways, the fat chick started performing CPR on Napalm, which turned into a casual makeout sesh, which then turned into straight up fellaysh.

Gary ended up leaving the bus with the girl and heading back to her parents’ AirBnB to take bourbon shots. Her dad was this 80-year-old dude (which makes me think she was probably an accident) that was on the bus too, and he proceeded to black Gary the fuck out in less than an hour. Then, apparently having had enough of him, the girl put Gary in her car and dropped him off at a house near UK’s campus that she knew housed some UK fraternity brothers of ours (whom Gary did not know). Why Gary didn’t just ask her to drive him back to our house, we’ll never know, but these random dudes let Gary crash there because #brotherhood. He ended up sleeping on their couch and taking a Lyft back to our house the next morning.


The story of Peter’s night is definitely my favorite one from the trip. After we got back to the house (sans Gary), Peter poured about 7 shots of bourbon into a big-ass mason jar, mixed in a little San Pellegrino, and began playing absolutely bizarre German pop songs that he somehow knew all the words to. Here’s one of them.

This didn’t surprise me, as my first memory of Peter (who is a few years my senior) is of him sitting in the back of the bus home from my freshman formal drinking Jamo from the bottle and screaming German obscenities.

The whole time Peter’s belting out these post-Derby German bangers he’s downing that bourbon drink and treating the back door like it’s a revolving door, repeatedly coming and going to blast heater after heater in the backyard. Eventually he and Brother Corey would end up heading back to his (German) car in the parking lot, hotboxing it with cigarette smoke, and revving the engine until it would red line, all because brother Peter claimed those were things that “cool and tough” people did. Peter is probably the world’s best drunk person.


Ben ended up walking in the pouring rain from the house to the bars and back after we got back from the Derby. I’m not entirely sure how far that is, but he left for the bars before midnight then racked up 5,000 steps on his Fitbit between the hours of midnight and 8:00 a.m., so I’m guessing pretty fucking far.

During his drunken stumble home Ben saw a backpack in the middle of the road, picked it up, and brought it back to the house. The next morning he opened it up to try and find out whose it is. The contents were as follows:

∙One (1) homework folder, high school

∙One (1) water bottle, empty

∙One (1) t-shirt, XXL

∙Five (5) tins of dip, empty

∙One (1) Dasani water bottle, 70% full of dip spit

This high schooler clearly has some vices he needs to work on, but, this being Kentucky and all, none of this surprised any of us. I was going to do some of his homework for him if any of it was unfinished, but our boy seemed to be up-to-date. I read some of his writing though, and it was not pretty. He got a Kentucky high school 85% on one of his papers, which I can tell you easily translates to a college 60%.

P.S. Check your trunk, Ben. Notice anything missing?

Such was my 2016 Kentucky experience. There are some things I’d change and some things I’d do the same, but I definitely have no regrets. As Ben so aptly said, “you can buy a door, but you can’t buy a memory.”

When it comes to the Kentucky Derby, I plan to go back every year. Just like my uncle’s horse, I want to never stop Derbying.

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Jared Borislow

Jared Borislow (né The DeVry Guy) is a Senior Writer for Grandex Inc and a 2015 graduate of the University of Wisconsin.

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