Hats, Horses, and Hooligans, are what defines the Churchill Downs Infield at Derby. But on the other side of the betting window, lies another realm. One filled with 50 cent tri wheels and super hi-fives. It’s where even the greatest of handicappers can have a bad day, and a couple mint juleps can lead to a four figure payoff. It’s the place newcomers and seasoned veterans come to celebrate the “Greatest Two Minutes in Sports.”
Taking bets at the infield at Oaks and Derby isn’t an easy gig. Supervisors at Churchill Downs will say that over the course of the day the average teller on Derby will handle more than $15,000. One big mistake and you could cost Churchill or any of its visitors a lot of money.

To prepare for my weekend at the Downs, I attended a class last week to master the Tote Mutuel machines. These are the little cashier looking devices that sit at every window at Churchill Downs. I’ts not incredibly difficult when you get the hang of it, but still making mistakes happens very easily.
Despite my best hopes of being placed in the iconic grandstands (tips central), I was delegated to the infamous infield for the weekend. I was about to take my first plunge into the Kentucky Derby in a trial by fire.
The Oaks Day went off without too much a hitch. Saw my fair share of inebriated gamblers. I was certain on a few occasions that many people weren’t quite positive on who they were betting on. Still, everything was relatively tame compared to the beast that is the Derby Day Infield.
I will admit, there was something absolutely magical about entering Churchill Downs on Derby Day. Despite being a transplant from New York City, I felt truly a part of the magical tradition that is the Kentucky Derby. Seeing the spires as I was carrying my wooden bar stool through the crowds was magnificent and something I won’t ever forget. It was touching as a sports fan, young person, and proud resident of this great city.
As the racing commenced the crowds starting pouring in. This begun the most crucial time period for a mutuel teller. Making friends. A betting window is like a bar, it has its regulars. Finding those regulars increases business for a bar and in the case of a teller…tips.
I made it my job to make friends with anyone who showed interest. I explained the difference of an exacta with or without a box at least 40 times. I made jokes like “may the Horse be with you,” and yelled “across the BOARD” whenever someone would make a win-place-show bet. Finally, I would make sure to tell everyone that when they won, “bring it right back here!” Soon enough I began to accrue a small following of betters.
I had Valerie, a middle aged woman from Henry County who only bet $2 to win on two Horses in each race. She won 5 times, and tipped a little more each time.
There was A.J. the seasoned handicapper, who had a soft spot for Horses with an Irish connection.
Finally there was Kevin, the businessman from Cincinnatti who was coming to Derby to “get money and get women.”
Valerie, A.J, and Kevin were among those that became the reason why I stayed excited and energetic through the hours leading up to the big race. Whenever I could spot a familiar face in the 40 person deep lines, it would help me to push forward and keep up my enthusiasm that brought smiles to many faces throughout the day.
Finally when it came to making my own Derby predictions, two older Latino men approached, I flashed my very disappointing grasp of the Spanish language and got a couple of tips. They were hands on the backside, and had been watching the Horses all week. Then one of the men finally said, “cinquenta dollares para Animal Kingdom,” or 50 dollars on Animal Kingdom.
I was astonished, I asked why they thought so strongly that a Horse that had never run on dirt could win the Derby. They smiled and asked me to “confian” or trust them.

I passed the advice along to my followers. They all called me crazy, most bet on Nehro and Decisive Moment. Yet, Valerie took the chance and put $5 win on the 16 Horse. I followed, taking advantage of my easy access to a betting window and placed a $5 across the board on Animal Kingdom and Nehro.
In the infield a hush comes about once the call to the post is made. People put down their drinks and find their spot to watch the race. A couple of friends who were also tellers accompanied me as we watched the TV right outside our line of windows.
I will admit, I had no idea who won for the first 5 minutes, I heard 14 over and over again, that I swore that Shackleford was victorious. Then finally Valerie ran up to the window.
“We won!” she screamed to me. After receiving her winnings she smiled and told me how much fun she had betting with me. She sprinkled a couple bucks into my tip jar and walked away.
As the day winded down and I left the Downs, I reflected on the day I had.
No, working mutuels at Churchill Downs wasn’t easy, but still it was a genuine way to experience the Derby and all the hoopla surrounds it.
Will I ever work Derby Mutuels again? No, I think I have had enough. I hope that my next experience at the Derby is on the other side of the windows.