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Our Kentucky Derby Trip

Kentucky Derby Churchill Down Steeples

The following is a blog I wrote five years ago, back in 2007, as part of a series about a trip I took with some friends to see the Kentucky Derby. While you might not know the characters, and you might feel like you are stepping into the middle of a story, just realize that it’s a good story, with good characters. This Kentucky Derby trip was a great experience.

After looking into buying some sombreros (it was Cinco de Mayo), then seeing every guy and his uncle wearing one on the news at Churchill Downs, we chose not to. We went down for our free continental breakfast and found out that orange juice in other states does not taste like our Florida orange juice. It tastes like Rosie O’Donnell sweat. The girls came out looking fantastic in their dresses and hats. I “accidentally” saw up Kate’s dress to find that she was also wearing cargo shorts underneath. I’m not sure, but I think she thought there were caves to explore in the Churchill Downs infield and she wanted to be ready.

We set off for Louisville to meet up with our Boston contingent. Evidently, the night before these five ladies went to a DJ AM party, hung out in the VIP next to Nick Lachey and some MTV chick. They were out until 4am or something. Once the Bostonians came down and got in their car, we could kinda tell they were feeling a little rough. They had to pour Kerri into her seat. That was the first indication these girls were going to be hurting all day. They all had the Jackie Onassis-look going on: big hat, black dress, dark sunglasses, looking like they were going to a funeral.

Kadoche followed the hungover ladies for about two exits, then he suddenly started cursing their womanly ways and pulled off on the fairgrounds exit. Seconds later, he realized he made the wrong turn. But I was riding shotgun, which meant I thought he was driving very well no matter what. We parked at some forklift lot and started drinking heavily. We were told the,re’s no chance we’re getting booze into the track, no matter what trick we tried. I thought allof us taking huge mouthfuls of booze, going through, then spitting it all back out into a red solo cup was genius, but I was alone. So we decided to smuggle all the booze in through our livers.Things have certainly changed since then.

Kadoche and I started the day off with a shot of Maker’s Mark, as is the local custom early on a Saturday morn, and that was the last lucid moment I had that day. We made kets, drank and ate as much as we could while tailgating, then we headed for the track. The bridge we crossed was like 40 times shorter going over than it was coming back for some reason. I still can’t figure that out.

The gate in which you enter the track to head for the infield is on a weird street corner. It’s almost like the stadium officials are ashamed of the infield patrons and they were trying to smuggle us in. There was no great big sign welcoming us. There were no good-looking vendors selling binoculars to watch the equestrian event. There was just Rubio … hitting on high schoolers. He did make headway with several students from Southeast Louisville Junior High just outside of the track, but we think they were only into him for a sip of his beer and because they thought he was a hobbit extra in Lord of the Rings.

Here’s a strange note: it was a cash operation to get into the joint. In other words, you didn’t buy a ticket. Actually, you’re ticket was Alexander Hamilton. No ticket windows to speak of. Just some dude, taking your $20. I don’t know. I’m thinking after 132 of these things, they would have come up with a more secure means of obtaining monies. Something tells me those ticket takers were paid well. And if they weren’t, then by the end of the day, they had several $20 bills tucked away in all sorts of places.

We went through the frisking area and Kate kept accusing her frisker of trying to take her flower, while Kadoche kept telling his frisker, “I don’t know what you’re looking for … but it’s a little to the left.” For the most part, the shakedown was kinda weak. We could have definitely brought alcohol in somehow. And while I did appreciate the Jello shots that Kadoche smuggled in, I was afraid to ask where he hid them and why we had to squeeze the Jello out of balloons. I’ve never had corn Jello before.

Walking into the tunnel to go under the track was eerie. It was neat for like 20 seconds. Then, once I realized I couldn’t see the light on the other side, I started thinking about how the entrance didn’t look exactly official and how we just handed a $20 bill to some random guy, just because he was standing there looking important. This tunnel, I thought, could just be a tunnel to the backyard of some Kentucky serial killer. I could visualize the different headlines, “Thousands march to death,” “Serial killer takes Gonos leftovers to work for three months,” and “Malcolm Found in Middle (Rubio) of Woodchipper.”

Anyway, we finally made it through the tunnel, found our Boston crew and set to partying.

Remember Maureen? Well, for whatever reason, she was the only one of the girls from Massachusetts that wasn’t dressed in black. Dobish pointed that out, looking at the pictures later and he just assumed they thought Barbaro’s funeral was about to take place. So I chatted Maureen up again, when one of the other ladies pointed out to me that Maureen’s name was not Maureen at all. It was Maura.

Me = douchebag.

It was at that point that I yelled at Soblotne because HE was the one that told me it was Maureen. He claimed he was innocent, but his shirt, which said, “I’m probably lying,” told me different. So I told Maura the story, apologized vehemently and begged forgiveness. She said, “You’re standing on my foot.” And I took that to mean all was good. I found out later that I was so buzzed that I told Maura the story of me getting her name wrong, like three or four times. Each time she just pretended that she was hearing it for the first time. That’s just plain evil.

Kentucky Derby Churchill Downs TunnelMeanwhile, Rubio was now hitting on everything that wasn’t wearing a saddle. He was persistent though, and he had some good opening lines. “Hi, wanna split a mint julep?” “Are you fromKentucky?” “Do you like Colombian coffee?” “You like air? SO DO I!” “Have you ever heard the term, ‘hung like a horse’ before? Well, I’m hung like a seahorse.”

The infield was interesting. You could see the grandstands where the civilized people were sitting. Queen Elizabeth II was in attendance, which prompted Soblotne to put on clean underwear. But in the infield, the class of people was certainly mixed. You had your fraternity boys dressed in their suits with pastel ties. You had your assortment of men just in their Fruit of the Looms. One guy was in his underwear, riding a pony-on-a-stick, with a rubber stamp with his phone number. He went to stamp his phone number on Courtney, but Soblotne stamp-blocked him.

We all drank mint juleps, the customary Derby drink, when we first arrived, and I have to say — I’d rather have a Drano-tini than have another mint julep. It was a vile drink. Toss in the fact that some mint leaves were muddled into the ice, giving it that drinking-from-a-ditch look, and the experience was not good. Oh yeah! And it cost me $10 for the privilege. (Although I did get a commemorative glass that I later broke … So I bought two more.) It was hot, too. I left Florida for a hotter state? Kentucky doesn’t even know how geography is supposed to work. The closer to the equator you are, the hotter it gets. Although it did provide some funny items. For instance, some of the Boston girls had eclipse sunburns on their shoulders because they were wearing those big hats.

We starting going with beer from then on, but the effects of the tailgating and the bourbon in the mint julep had taken their toll. I remember at one point, I called my family back in Florida to say HI! (My mom was having a get-together at her house and I wanted to check in with everyone.) I was a little inebriated and at one point, Tabitha, one of my cousins, asked me if I saw the Queen, to which I responded, “See her!?! Hell, I motorboated her!” Then she notified me I was on speaker phone. Grandma did not approve.

Kentucky Derby Churchill Downs nutcaseThroughout the morning and early part of the afternoon, I had been looking over the information on all the horses. I’ve never bet on horses before in my life and this was an event, so I thought it prudent to do so. I had like $80 ready to waste. I talked with Tina and Kadoche, both of whom were savvy veterans at the ponies. But I didn’t talk to them enough. The WAY you bet on horses is a little different than anything else. I didn’t have a degree in horse wagering and later on in the day, some extremely simple rules came to mind for the NEXT time I go to bet on horses.

Rule No. 1 — Never bet on horses when you’ve been drinking heavily.

You’d think that I could have figured that out ahead of time, but no. I’m an idiot. Also, since I had the lowdown on all the horses in my pocket, our Boston friends (who up to this point had been napping, eating, sitting and pretending to be people mannequins) asked me about some horses. I told them that we were about to go up and make our bets at the window and I’d be glad to make theirs for them.

Rule No. 2 — Never make bets for other people when you don’t know how to freakin’ make a bet yourself.

So after explaining to them that they could make a $2 box trifecta bet on three horses to come in first, second or third in any order, I took several bets from several people. Silvia even wanted a $10 box trifecta bet.

Rubio passed out on a passed-out KerriSoblotne, Maura and I got into the Disney-like line at the betting windows and we started chatting with all of the other derelicts in the area. Soblotne can’t get enough of messing with people’s heads. “You’re from Louahville? See? I knew it was called Louahville. My buddy thinks it’s pronounced, ‘Lewisville.'” (I heard this happening behind me, so I took the cue when they asked me what city we were in and called it Lewisville. It’s fun being an idiot on purpose. Other REAL idiots want to talk to you forever.) The same group of people had someone with them from Breckenridge,Colorado. I said I had a second-cousin from Breckenridge, then I pointed at Soblotne and said that HE had a BUDDY that had a second-cousin from Breckenridge (meaning me). They were amazed.

With this circus of idiocy going on around Maura, and me telling her the story about me calling her Maureen for the ninth time, her patience was thinning. She needed to get back to her hung-over friends that were having a boring-off. Compared to their group, we must have looked like a second-grade class on a field trip to a candy factory.

I got up to the betting window, not really paying much attention to the people making their bets ahead of me, and I started making my wagers. Looking back, I should have researched more by reading the Daily Horse Picks beforehand. As I said, I had my group of bets, mostly box trifectas, and about $40 worth of bets for the Boston girls. After making the bets, the lady asked me for $210. Meanwhile, Soblotne is taking pictures of some random chick dry-humping me from behind. I paid the tab and walked away, trying to do the math in my head.

I paid nearly $100 more than I expected. Apparently, a box trifecta means you are making SIX bets. So if you make a $2 box trifecta, that’s a $12 bet. Silvia’s $10 box trifecta was actually a $60 bet. I went back and told Silvia and the girls. They were unimpressed by my misfortune. Silvia did offer to give me more money, but at that point, I was more embarrassed by my stupidity. So she and I REALLY became fans of the three horses she bet on.

It was close to post time (I still have no idea what that means) and a group of us went to walk across the entire state of Kentucky to watch the horses come through the first turn. Why we had to walk to the completely opposite side of the track to where we were sitting, I asked not. I was still trying to think of how I could ask for a betting refund at the windows.

Kate, Rubio, Soblotne and I ended up standing near a tent at the end of the front stretch. We could see the grandstands, the video screen, a hot dog vendor, some drunk people and I think I even saw the Queen — or at least a gay guy.

Kentucky Derby Churchill DownsThe race was about to begin and you could literally feel the excitement in the air. I looked over at Rubio and he told me he made a last-second big money bet on one horse to win. He wouldn’t tell me what horse it was and I didn’t ask. I did ask him, however, if he’d like me to just kick him in the balls — anything that happens after that is like a trip to the circus.

Here we were, on a Kentucky Derby trip (just “the Derby” to those in the know). The most exciting two minutes in sports. This is one event I got to check off on my list of things to see before I die.

  • Super Bowl
  • Final Four
  • Big Momma’s House 3
  • Wimbledon
  • Indianapolis 500
  • Dwyne’s wedding … to a woman
  • American Idol quarterfinals
  • The Masters
  • StanleyCup Finals
  • 12 naked women in my bedroom

The excitement was palpable. I don’t even know what that means. The race finally started and as the crowd surged, I could tell the horses were approaching. Then everyone’s heads in front of me turned from right to left … and I guess the horses passed us. I’m 6-foot-2 and I didn’t see a thing. Actually, I thought I saw a couple horses, but they could have been some really fast fat chicks to be honest. So I watched the video screen above me to see how my/Silvia’s horses were doing … We would have done better betting on the fat chicks.

The race ended and a guy behind me went crazy. He hit the trifecta and was up a chunk of cash. “Street Sense” won the race. Yet if I had any “street sense,” I would have known how to make a bet correctly. Irony, thy name is Gonos.

I started to think of a way to shake down Silvia for more cash, and then I happened to look over at Rubio. He was so pale he was nearly transparent. He was kind of holding his head in his hands, muttering something in Irish/Spanish about how he has to sell his sperm again to pay off this bet. The first thing that came across my mind was, “I don’t think he bet ‘Street Sense.'” The second thing that came across my mind was, “Don’t ask to borrow $80 from Rubio.” I’m good at reading people. After he got done crying on his hands and knees in a mud puddle and finally took the gun away from his mouth, I asked him, “How much did you win?”

Kentucky Derby Churchill Down SteeplesWe walked back to our hangout spot. The infield was emptying quickly and the Boston girls followed suit. I told Moesha goodbye and she was on her way. Somehow, every bet that Courtney made for her friends at work came through a winner. So Kadoche and I joined her at the payout line. I watched as the cashier paid out each ticket individually. It was amazing to me how non-technological the payout system was. The girl added stuff in her head. Seriously. And to be honest, not only did I think she’d have trouble doing long division, I thought she’d have trouble spelling long division. Kadoche had also made a last-second bet on the race that followed the Derby (yuh, there’s like 12 races that day!) He won back a chunk! I think I was the only non-winner in our group — unless you count Soblotne, just in general.

Finally, we made our way out, through the tunnel, over the 9-mile bridge, then out of the city of Louisville. We really didn’t get to see much of it actually, but we were caked in mud, trying to keep Rubio from taking a handful of sleeping pills, and heck, Tina had like 152 stories left to tell that I had to roll my eyes at. There just wasn’t enough time in the day.

The best way to describe the infield at Churchill Downs is that Easter Sunday,Woodstock, Spring Break and a Jimmy Buffett concert had a baby in Kentucky. We saw some pukin’. We saw some boobies. We saw some people win big bets. We saw many more people lose bigger bets.

Without question, I had a blast on our Kentucky Derby trip and I suggest others check it out as well. While I didn’t get to see much of the race, the energy from the crowd and the party atmosphere was worth the trip.

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