The Chronicles Of Todd: The Kentucky Derby, Part I

The Chronicles Of Todd: The Kentucky Derby, Part I

He emerged from the plane with his blazer slung over his arm and a weekender bag filled with three outfit changes, his dopp kit, and his recently refilled Adderall prescription. Taking off his sunglasses, he squinted across the airport’s gate area looking for John and Finn who were sitting at a Fridays both with a glass of Kentucky Bourbon sitting in front of them.

“Look what the fuckin’ cat dragged in,” John yelled across the airport loud enough for everyone within an earshot to hear. Todd couldn’t contain the grin on his face.

“We made it, boys!” he yelled back before sitting down next to them and looking towards the bartender. “Angel’s Envy, neat.”

John and Finn flew in about an hour earlier than Todd and had clearly already had drinks on the plane. At this point, it was only ten o’clock on Friday morning and they were unsure if they were going to make it to The Oaks or sightsee around Louisville prior to heading out that night.

Todd hunched over his drink and leaned into the table. “I didn’t come here to not bet on some ponies. We’re goin’ to the fuckin’ Oaks.” The threesome erupted in laughter while each taking their drinks in their hands and drinking them down. “Alright, let’s drop this shit off at the Airbnb and just roll from there.”

Upon getting in the Uber, they immediately asked to pull over to go to a liquor store and pick up a bottle of Woodford Reserve prior to their arrival at the house Finn had booked weeks in advance.

“Let’s just ditch the bottle and our shit and go straight to the track,” John said. “Sanjay, can you wait for us to drop this stuff off and we can just continue the trip?” He nodded in agreement before they all piled out of the car and made roadies before re-entering the Kia Rio less than ten minutes later.

As Todd entered Churchill Downs as the Uber’s new destination, he let out a sigh of aggravation – “Fuck, my phone’s at 19% battery.”

“You’re not going to have service there anyway,” John told him. “Your phone’s as good as dead all weekend.”

Todd slid his phone into his blazer pocket and shrugged it off. His voice raised a little before saying, “Proooobably gonna hear about this one when the weekend’s over.”

As the traffic built up surrounding the track, they agreed to have Sanjay drop them off a few blocks from the entrance. Approaching the front of Churchill Downs, they swigged the rest of their roadies and ditched the cups in a bush for fear of law enforcement seeing their open containers.

“Hey, can I score one of those Adderall?” John hesitantly asked Todd.

Todd reached into his pocket and picked one out. “Does a bear shit in the woods?” Todd asked. “Of fuckin’ course, you can. It’s fucking Derby weekend, man.”

There was hardly a line near the box office where they needed to buy their tickets for the day. A perfect 73º and sunny, it was evident that the crowd would only grow from that point on. Todd was the only one with any Oaks or Derby experience, so he warned everyone to leave some in the tank on Friday before the races on Saturday.

They entered the tunnel to head to the infield not truly knowing what to expect. The lines outside were minimal, and it was still fairly early in the day. But as they emerged, they saw thousands of people dressed largely in pink, as is Oaks tradition. At this point, they needed to make three stops — ATM, the betting booths, and a bar, all in that order.

Approaching the ATM, the line was longer than they anticipated. “Fuck, remind me to get money out beforehand tomorrow,” Finn said while on his tip-toes trying to gauge how long it would take. “Fuck it, I’ll go get us drinks while you guys wait in line here.”

Todd and John took out their programs and randomly started assigning horses as “their horse” despite not actually knowing anything about said horses. Looking back to see if Finn was in tow with their cocktails, Todd looked behind him and saw a group of three girls all dressed identically — knee-length Lily Pulitzer dresses, oversized sunglasses, and hats appearing to be about two-feet in diameter. He nudged John and whispered, “Get a load of the talent behind us.”

John looked back with raised eye brows and confirmed what Todd had seen. At this point, they were a few people from the ATM with no Finn in sight. When they were finally able to take their money out, John said, “Todd, watch this.” Todd looked down to see John leaving his ATM receipt in the machine for the girls behind them to see. Laughing, Todd jokingly said, “Wow, you’re a real piece of shit,” as they left.

But upon turning around, John looked at the three girls and simply said, “Ladies,” while walking past them.

“Jesus,” Todd muttered. “Too early for that kinda trouble.”

When the finally tracked back, Todd noticed Finn standing at a bar ordering three Woodford Juleps. As they approached him, all Todd could hear him say to the bartender was, “Can I grab a couple floaters on these?”

Looking back with the grin of all grins, Finn told both of them to enjoy as they all smiled and agreed to head to the betting booths to throw down some ill-informed wagers.

“You should’ve seen the girls we just saw back there,” John told Finn. “Like, I know you’re married, but my God they were scorching.” Finn laughed while explaining that good looking girls at Churchill Downs were a dime a dozen.

“Okay, okay, I get it, you’re married,” John continued. “I’ll point ’em out if I see ’em again.”

They stood in a much shorter line to place their wagers. Each of them admitted to one another that they hadn’t done any research prior to The Oaks and had only looked at Saturday’s horses. “Honestly,” Todd began, “I probably shouldn’t be betting today but fuck it. Gotta make things interesting.”

Todd reached his head towards the booth and shouted out a slew of names before handing a woman $100. She wished him good luck and he turned around while stuffing his four betting slips into his chest pocket. Finn and John stood directly behind him waiting for their turn to place their bets as Todd looked off into the distance over their heads. He tapped John on the chest with the back of his index and middle fingers with a smile.

“Hey, look. Here comes trouble.”

Read The Chronicles Of Todd: The Kentucky Derby, Part II.

Image via Shutterstock

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Will deFries (Twitter / Instagram) is a Senior Writer at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram). Email me at

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