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I began my Kentucky Derby day with what I thought would be a terrible omen - I woke up because I had received a text from my boss informing me that he was waiting in the lobby of the hotel for a ride to the track. While typing a frantic “Be right down!” reply, I threw on a dress, ran a comb through my hair and grabbed my camera and computer. I actually made it downstairs in about ten minutes, but it wasn’t an auspicious start to the morning. 

Fortunately, my day very much improved from there. The Kentucky Derby is really unlike any other race of the year; people are there to put on a show just as much as the horses are, and there’s a level of pageantry that’s incomparable to any other event (horse racing or otherwise) that I’ve ever been to.

So I was ready for anything when I got to the races, and I was not disappointed. I had just put my computer and various equipment in my workspace when the announcement came over the loudspeakers that the garland of roses the Kentucky Derby winner would wear was arriving. So I, along with a myriad of other photographers, hustled to the entry gate to get a snap of the storied flowers.

When the vans arrived, it was like a Presidential motorcade. Seriously: There were three cop cars, a dummy florist’s van two cars back and a whole slew of personnel attending the roses. In other words, it was perfectly over the top in a way that’s totally appropriate for the Kentucky Derby.

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When the flowers were unloaded I had one thought: That the carrying case looked exactly – but exactly – as I imagined Snow White’s temporary storage tomb looked as she awaited Prince Charming’s wake-up kiss. Sorry if that’s a bit morbid; but seriously, look at it:

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Once you see it, you can’t unsee it. 

Anyway, after watching the roses be delivered to Churchill Downs, I decided to go people watching for the best and worst of Derby hats. I have a spot that I love to go to in order to get photos of hats: I basically climb halfway up one of the columns on the main Churchill Downs building like an insane monkey and take photos of people who have no idea that I’m there. Side note: that is the creepiest sentence I’ve ever written about myself. Here’s the view from that spot:

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Anyway, due to my aforementioned creepiness I have about 1,000 photos of the good, the bad and the inexplicable headgear that people bring out for the Run for the Roses, and here are some of the ones that stood out to me.

Honestly, the hat below is the millinery equivalent of that spooky house one block over that had baby doll heads hanging from trees. 

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If you look closely at the photo below, you will see that the flamingo on the lady’s hat is also wearing a tiny straw boater trimmed in blue grosgrain with white polka dots. Say what you will, people, but that is commitment to a theme. 

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I dunno; in a way I love it. That is so much hat on such a petite woman that I’m kind of convinced that she must have the neck strength of a linebacker. 

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I genuinely loved the two hats below; these ladies looked wonderful and so put together.

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One day I will look this put-together, relaxed and confident. (Actually, let’s be real: probably not.) 

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I am seriously in love with this lady’s dress – check out the jockeys’ silks on the bottom! And I adore that she’s wearing an actual riding helmet – that’s showing some sass, and I approve.

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I decided that my next stop would be the infield, which is one of the more hilarious places on Earth on the first Saturday in May. People are there for a party, and their outfits reflect that perfectly. Check this action out: 

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Greetings, Mr. Mayor! I like your style.

Here are some of the other bold and brash outfits I saw:

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I saw this … person as a race was running:

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After I took this picture, he tried to give me a hug and I literally backed away with both of my hands in the air repeating, “No, thank you. No, thank you. No, thank you.” I’m sure that he’s really a very nice man under there, but that mask is terrifying. 

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On a happier note, I ran into these gentlemen who were at the Derby to support Wicked Strong. That’s the horse whose owners have pledged a percentage of his earnings from the Triple Crown to the One Fund in support of the Boston Marathon bombing survivors. It’s a wonderful cause, and I was thrilled to see some Beantown supporters in the ‘Ville for the Derby.

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I also ran into this guy, who was playing the drums and making up songs about the people who passed by. He was really good, and when I stopped to take his photo, he made up a song about me! So obviously I had to stop and have a one-woman dance party. It was awesome. And he also said that I helped him get some business, so that was a fantastic bonus!

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After hitting up the Infield, I decided to skibble over to its polar opposite, the red carpet. This is where celebrities are ushered into the Derby, and you can see some serious stars (and some D-listers, which I actually like more.) Here’s NBA Star and recovering Karadashian spouse Kris Humphries: 

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The very chic lady below is Lucie Arnaz, the daughter of Lucille “I Love Lucy” Ball and Dezi Arnaz. That’s Hollywood royalty, folks. She is stunningly beautiful in real life, by the way.

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Check out what Joey Fatone of *NSYNC fame wore to the Derby! I mean, this is why I love the C- and D-list celebs. They come dressed to be remembered, and if they will be remembered because they look absurd then so be it. 

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My next stop was the roof of Churchill Downs: there was a big race coming up, and I love seeing the Derby scene from a bird’s eye view, so the timing was perfect. Also, let’s face it: it’s a super-restricted area (just a few photographers and a bunch of government snipers) so I just like going up there because it’s cool as hell. 

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The race I was there to see was the Churchill Downs Turf Mile, a race for fillies and mares going, well, one mile on the grass. (Captain Obvious here to help you out, y’all.) The view was incredible, and I could catch the entire race with ease on my trusty little Nikon. 

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By the way, if you’re curious as to just how massive the new video board is at Churchill Downs, check it out in comparison to the 1,000-pound racehorses running below it: 

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That’s massive.

At the end of the race, Coffee Clique prevailed over Dame Marie to take home the lion’s share of the $300,000 purse.

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With that, my rooftop fun was over since it was time for me to head down to the main track to cover the rest of the afternoon’s major races.

The very next stakes race was the Humana Distaff; this is always a hotly contested event for female horses four years old and up traveling 7/8 of a mile, and I was eager to see Judy the Beauty (one of my favorite racemares) and Midnight Lucky (a very pretty gray filly).


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After the seven furlongs (the horse racing term for 1/8 of a mile) it was Midnight Lucky cruising home all by her lonesome with Rosie Napravnik aboard.

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As we waited for Midnight Lucky to come back to the winner’s circle, I loved seeing her human connections’ delight at the win.

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While Judy the Beauty didn’t have the best race of her career, she came back in good spirits and I hope to see her run again soon.

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When Midnight Lucky and Rosie got back to the winner’s circle, Rosie was all smiles; and, in typical fashion, she was sure to give her horse lots of pats for a job well done.

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The next major race was the one that I was most nervous about for the whole day. That’s right: more than the Derby. Because my boy Wise Dan was defending his win in the Woodford Reserve Turf Classic, and I love him (as regular readers of this blog know) more than any other horse running right now. I have a word I’ve coined for my state of nervousness that consumes me every time Wise Dan runs, and it was taking full effect before the Woodford Reserve:

I planted myself on the rail of the turf course and got ready to shoot the race with my heart in my throat. As the race began, Wise Dan looked fantastic and I got a great shot of him heading down the stretch for the first time.

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But right after that, he got into a little trouble and my stomach plummeted. As the race continued, I had a steady chant of, “Come on, Danny Boy,” on loop in my head. I just wanted a safe trip for him, and thankfully that’s just what he got.  Heading for home, a very game Seek Again challenged him, and as the pair hit the wire I honestly had no idea who won. 

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Talk about a tight finish! But in the end, my man Dan showed the depth of his heart and stuck his head in front to win the Woodford Reserve. What a horse he is!

One of the things that I love so much about Wise Dan is his personality. The horse grins after he wins races – I’m not making that up. So I love this photo that has him and his jockey John Velazquez wearing matching smiles as they make their way back to the winner’s circle. 

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When they arrived, Dan was welcomed home by his human connections. While I wasn’t able to see moment this in person, if you need proof that his trainer Charlie LoPresti loves his horse, look at how he thanked Dan in the winner’s circle:

Dan wasn’t the only one getting hugs that day: here’s Bo Derek embracing jockey John Velazquez after the win: 

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It really was an amazing moment, and I am so, so glad that I was there to witness it.

With that, it was time for the main event: the Kentucky Derby. I hustled to my spot on the dirt track rail to make sure that I could get good photos of the walkover. The walkover is when the Kentucky Derby horses and their human counterparts (aside from their jockeys) make their way from the barn area to the saddling paddock. It’s incredibly cool, because the crowds are cheering and it’s the first look that spectators get of the horses all in one place. 

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My absolute favorite part of the walkover this year was seeing Tony Danza. I mean, first of all he’s awesome; and he was at the Derby as the guest of Eclipse Thoroughbred Partners, who own Danza (the horse). Tony was clearly having the time of his life, and as he walked past the grandstand he was high-fiving fans and yelling out, “Go Danza!” I think he made a lot of life-long fans that day.

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I may have geeked out a little when I saw him. I know I had an absolutely ridiculous grin on my face and that I repeated, “Hi, Tony Danza!” at least ten times. What can I say? I am not above being star-struck. 

As I waited for the Kentucky Derby horses to emerge out of the paddock, I took a moment to check out some of the fabulous hats in the crowd. Check these out!

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Special kudos to this couple, who coordinated their outfits to wonderful effect: 

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Finally, it was time for the post parade and the singing of “My Old Kentucky Home.” This is one of my favorite Derby traditions and one that brings tears to my eyes every year. As the horses parade in front of the stands, the crowd gets to its feet and sings the Kentucky state song. It’s a tradition steeped in history, and it gives me goosebumps every time.

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And then it was time. The gates sprung open, the crowd roared, and suddenly 19 of the best horses in the nation charged past the grandstand for the first time in a bid to make history as the 140th Kentucky Derby winner.

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Two minutes later, it was California Chrome hitting the wire all alone in a victory that was breathtaking. The ease with which he won was incredible, and his jockey Victor Espinoza raised his arm in salute to the win as he crossed under the wire.

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After the win, I hustled over to the turf course to stake out a good place to take photos of our newest Kentucky Derby champion. On my way there, I saw my dear friend (and amazing photographer) Zoe Metz who is firmly on Team California Chrome. She was getting a big hug on the track, and I was sure to give her one right after this! As I tweeted afterwards,

When I was in the winner’s circle (it was my first time having access to it, and let me tell you: it is AMAZING!) I was privileged to be able to get photos of jockey Victor Espinoza and California Chrome’s triumphant return. The joy on Victor’s face speaks volumes about how winning the Kentucky Derby must feel. 

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And this is what was waiting for him: the winner’s circle that all owners, trainers and jockeys dream of visiting:

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When California Chrome was ready, his entourage of humans posed for their Kentucky Derby winner’s circle photo:

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Then, it was California Chrome’s time to go home and rest. To be honest, he didn’t even seem tired as he left the winner’s circle. This little horse was so impressive, and his connections are genuinely good people. I hope in my heart of hearts that he’s the one: the horse to end our 36 year drought of Triple Crown winners.

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After California Chrome left, it was time for his humans to celebrate. By the way, if you’re curious as to how it feels to win the Kentucky Derby, let jockey Victor Espinoza and trainer Art Sherman show you:

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As Victor raised the Derby trophy in acknowledgement of his win, I reflected on what a wonderful journey he had with his Kentucky Derby winner California Chrome and how much excitement lay in front of the pair in the weeks to come.

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Thank you all for joining me this Kentucky Derby week, and I’ll be back with much more in my Preakness Diaries next week! In the meantime, let me know in the comments what you thought of Kentucky Derby day and what your favorite moment was.

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Penelope Miller

I'm Penelope Miller and I'm the Senior Manager of Digital Media for America's Best Racing. I've been involved with the Thoroughbred industry for most of my life and I want to make sure that the great sport of horse racing is enjoyed by people all over the nation. Please share your thoughts and ideas with me in the comments section below!

Image Description

Penelope Miller

I'm Penelope Miller and I'm the Senior Manager of Digital Media for America's Best Racing. I've been involved with the Thoroughbred industry for most of my life and I want to make sure that the great sport of horse racing is enjoyed by people all over the nation. Please share your thoughts and ideas with me in the comments section below!

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