They’re people who the rest of the world rely on to make their Kentucky Derby Experience the event of a lifetime, time after time. While their roles are wildly different, each one plays a critical part and each one feels that pressure to deliver perfection. Rocko Jerome grabs a few moments with a some of the hardest-working people behind this magical season.

Photo by Clay Cook

The phenomena that is the Kentucky Derby extends far beyond Churchill Downs. It’s a global event with ripple effects reaching into every corner of our city and state thanks to a sometimes-unsung cast of supporting characters. This legendary race has been spun into a season that is bolstered by entrepreneurs, milliners, media personalities, event planners and visionaries who all play a role in maximizing the two-minute race into a once-in-a-lifetime, over-the-top celebration for locals and out-of-towners year after year.

On our cover, we honor a select handful of stalwarts who have made their personal imprint on the way the rest of us do Derby. Here, they share their thoughts before the gates open on Kentucky Derby 145.

Co-Founders of The Unbridled Eve Gala

What does a successful Derby season look like for you?
Tonya: I would say that our primary goal is that our volunteers, guests, and attendees leave with a great feeling after being a part of Unbridled and that we raised money and awareness for some really vital causes. Our intention is to present a world-class event that puts Louisville in a good light during this special time and in the end, when I feel like we did that, it’s a great year.
Tammy: I’m just happy when all the pieces fall together. It’s like watching a duck gliding across a pond, where it looks so effortless but what you can’t see is that there’s a lot of hard paddling underneath.

How does it feel to have created a gala that is so closely tied to this iconic event?
Tonya: I feel that the most important thing is the sense of interconnectivity that Unbridled creates. We are so fortunate that our attendees and sponsors are such amazing and smart people. Just like in any effort, we’re all stronger together. I take a great deal of pride in that.
Tammy: For our part, it feels like we’re right where we should be. It all circles back to the reason that we started and our constant goal, which is to make a difference beyond just this event. Unbridled is a tool. It creates a certain sense of value towards economic development and philanthropy that continues throughout the year. That has always been very important to us.

What’s your best Derby memory?
Tammy: The year that Luke Bryan performed for us. He had just been named Country Music Entertainer of the Year for the first time a few months previously at the CMAs, so there was all of this buzz and excitement around him. He and his wife Caroline couldn’t have been sweeter or kinder. I’ll always remember that the next day on the Derby Red Carpet, he ran over to me and excitedly asked “Do you know how much we raised?”
Tonya: As much as I love what we do on Derby Eve, my recurring favorite memory is actually from Derby Day every year when a group of us from the event all gather on the balcony over the track as they play My Old Kentucky Home. I get chills just thinking about it.

What was your most surprising Derby moment?
Tonya: One year, Ian Somerhalder (Star of Lost and the Vampire Diaries) grabbed me and asked me to walk the Churchill red carpet with him. That was pretty fun and very unexpected!
Tammy: Our first year, we had to create a tented area over a terrace so that we could have enough space for the silent auction items, and wouldn’t you know that there were hurricane force winds and rain that night. It actually ended up getting so bad late into that night that the top of the thing collapsed and poured buckets of water all over me, in my ball gown. I kicked off my shoes and just made a mad dash to try to save all these lovely donated items that we were auctioning off, and I just couldn’t stop laughing.
Everybody was concerned that I had snapped, but it was just such a completely crazy thing to happen at that moment that all I could do was crack up at how ridiculous it was. What can you not predict when you’re planning an event? That a waterfall will pour from the ceiling! In the end, we saved everything, but I will never, ever forget that moment and I still laugh about it.

Owner of Formé Millinery

What does a successful Derby season look like for you?
I love Derby season because of the feeling of excitement everyone has about the events. It means that people put that extra effort into what they wear, and it means so much that I get to be a part of making their wardrobe come together. I always say that for each person I style, it’s like planning a little personal wedding; the hat is the final touch that’s really giving a bride her complete look. So, I’m successful when my clients look nice, stand out in a hat that is unique, and most of all, feel special in the hat that I made just for them.

How do you feel about your work being a part of this iconic event?
It’s truly an honor. You know, being a master milliner truly means having a life of service. Creating a hat for my clients can be very personal. I learn so much about each of them and the hat we create together becomes a little bit of the both of us. I love that hats are still a tradition. At Derby time there’s a kind of a seasonal novelty to them and I think that’s fantastic, but there are also people for whom hats are a perennial part of their outfit every day, all year. I mold these hats for my clients using a technique that few people in the country still use, it involves molding them over a block of wood that’s over 100 years old, so the basis of their hat has this historic pedigree before I begin to add the unique features to it. No two are alike, and that’s important to me and my clients.

What’s your best Derby memory?
It has to be a couple of years ago when NBC did a feature on my hat shop and the art of millinery that ran during Oaks and Derby. Bob Costas came and checked out what I did, then showed it to the world. I’m very proud of that and to have represented the millinery industry.

What was your most surprising Derby moment?
I’m always a bit surprised by how late people sometimes wait to start to plan! I know that everyone is busy, but the custom process that I use takes a little bit of time. The absolute minimum to get a hat together for someone is five days and when it’s Derby season, the orders add up. It takes a great deal of care and effort, and I really insist on putting my best effort into every single one. You are going to be wearing your hat for many hours, so it is important to find the right hat that is comfortable, fits properly, and compliments your complete outfit and physique. I’m surprised every year by how late some people push it in terms of finding their hat. I have people coming in with custom requests on Oaks. I’m sure I’ll be surprised again this year!

Wave 3 Weatherman, Derby Anchor

What does a successful Derby season look like for you?
Sunny and 72 degrees! That’s what we all want, right? The question of what the weather will be like on the upcoming Derby Day pretty much comes up on the day after every Derby Day, 364 days prior, and keeps building steam through the year. I think that’s because in this area at this time of year, just about anything can happen. It could rain or snow or be really terribly hot, or we might get lucky and have a really nice one. Meteorology is an inexact science and people are pretty forgiving about the forecast most days...but Derby Day is special for a whole lot of reasons!

How do you feel about being a part of this iconic event?
It feels fantastic, even as just a native of Louisville, annually witnessing this awe-inspiring tradition. Even beyond forecasting the weather, I really enjoy being in a position where I can research so many different interesting things associated with the Derby and then present them to the public through WAVE 3. Here we are after a lot of years, it’s still exciting on every level.

What’s your best Derby memory?
Oh, there are so many. I worked on stories about people like Bill and Susanne Juaire, the couple up in New England who handcraft the Derby Trophy every year. Those are truly a wonder to behold. I’ve been fortunate enough to be just about everywhere in Churchill Downs on Derby Day, including up inside of the twin spires. The view from up there is just absolutely breathtaking. Being able to see the athletes in person behind the scenes as they get ready is fascinating.

What was your most surprising Derby moment?
Last year when it would just not stop raining. Every bit of meteorology told us that the rain would be gone by noon. Then it seemed that there was no way that it would last past 4:00, and even if it did, it would certainly be out by race time. And it wasn’t. It just wouldn’t go away, and I felt terrible. If you saw a guy walking around hiding his identity with a bag over his head, that was me. We’re hoping for much better this year.

Kentucky Derby Festival Chief of Staff

What does a successful Derby season look like for you?
We at KDF just want our patrons to have really fun and memorable experiences. Our goal is to create varied programming that the entire community can get into, and it makes me happy to know that all kinds of people get to enjoy the whole festival in different ways. Also, I know that it seems like a really easy answer, but I just really hope for nice weather throughout. A gorgeous day for Thunder through to a clear and temperate Derby day. We plan our programming all year, then it’s just up to Mother Nature to help us stick the landing!

How does it feel to be a part of this iconic event?
You know what? It’s been 30 plus years for me with KDF, and it still feels great. Everywhere I go, even if people don’t know my name, they will yell out “Hey, it’s that Derby Festival Lady!” I think it’s fantastic, even though I never meant for this to become so much of my identity. I suppose that I hope that who I am has affected what KDF is at least a little bit as much as KDF has affected who I am.

What’s your best Derby memory?
There have been so, so many and they all sort of blur together a bit, but a big standout for me has to be in 2010 when the movie Secretariat came out. We had Diane Lane and Penny Chenery herself, Secretariat’s owner, here for the Festival this year. That movie was in the making for a long time and it was already really exciting to have it finally come out and turn out to be so great. Plus, to have such a great actress and a real historical figure here for it... It was really cool. I just loved it.

What was your most surprising Derby moment?
Oh my gosh (laughing). It’s funny now, but it wasn’t at the time. In 2012, we had Cyndi Lauper at the parade. She had this mix-up about whether or not her mic was on. She thought it wasn’t, it was, and she ended up dropping an F-bomb on live television. It was quite a panic for us behind the scenes. It was uploaded and totally viral around the world in a hot minute. I wish it hadn’t happened and it was embarrassing, but I think everybody was ultimately okay in the end. What can I say, anything can happen at the Derby!

Clothing: Teri Jon pink gown on Tonya York Dees, $600, and Theia silver gown on Tammy York Day, $595, both at Rodeo Drive. On Chloe: Elizabetta Franchi bodysuit, $375, and pants, $345, and Rebecca Minkoff handbag, $248, all at Rodeo Drive and Forme by Jenny Pfanenstiel fascinator, $485, at Forme in Mellwood Arts and Entertainment Complex. On Stacey: Chiari Boni dress, $695, at Rodes For Her. Forme fascinator on Jenny: $435, at Forme.

Jewelry: All jewelry provided by Davis Jewelers, prices and descriptions clockwise from top: On Tammy: David Yurman Tides ring in 18K yellow gold with morganite and diamonds, $4,500. David Yurman Chatelaine drop earrings in 18K yellow gold with rutilated quartz, champagne citrine, and pink tourmaline, $2,650. David Yurman Chatelaine linear bracelet with diamonds and 18K gold, $3,650. David Yurman Chatelaine linear necklace with diamonds and 18K gold, $7,900. David Yurman Chatelaine bypass ring with 18K gold and diamonds, $900. David Yurman Chatelaine ring with 18K gold and diamonds, $1,300. David Yurman Buckle bracelet in 18K yellow gold with diamonds, $2,500. On Kevin: Longines stainless steel Master Collection Chronograph with brown alligator strap, $3,000. David Yurman Deco signet ring, $525. On Stacey: David Yurman Tides wide woven cuff with diamonds, $3,950. David Yurman Chatelaine bypass ring with diamonds in blue topaz, $900. David Yurman Chatelaine linear chain earrings with blue topaz and diamonds, $2,650. David Yurman Tides dome ring with diamonds, $2,400. David Yurman Tides pendant necklace with diamonds, $2,700. On Chloe: David Yurman Crossover chain drop earrings with diamonds in 18K gold, $2,550. On Tonya: David Yurman Continuance center twist bracelet in 18K gold, $3,500. David Yurman Pure Form smooth bracelet in 18K gold, $5,500. David Yurman Pure Form collar necklace in 18K gold, $1,950. David Yurman Starburst ring with diamonds in 18K gold, $4,100. David Yurman Stax wide ring with diamonds in 18K Gold, $3,900. David Yurman Continuance full pave small drop earrings in 18K yellow gold, $4,800. David Yurman Starburst pendant necklace in 18K gold with diamonds, $5,400. David Yurman Continuance center twist bracelet with diamonds in 18K gold, $3,900.

Posted on 2019-04-05 by Christine Fellingham