Kentucky Derby Diaries: From Rooftop to Racetrack on Derby Day

The Kentucky Derby is unlike any other sporting event in America; half of the day is a celebration of unparalleled Thoroughbred racing, a quarter is an ongoing fashion show, it has a little bit of old-school sophistication and the rest is just one big party. It’s one of my favorite (if not most exhausting) days to cover of the year because it’s always such a spectacle, and this year’s edition certainly did not disappoint! 
After arriving at the track at about 8 a.m., I set my gear up in the media center, guzzled about three cups of coffee (not an exaggeration; it takes a lot of caffeine to get me perky in the morning) and started to put together my cameras. I really love covering the Derby because you see some sports writers and photographers there that you may not see any other time of year. It becomes kind of like a high school reunion (except the coolest kids are the nerds who love to write and play on computers.) It’s fun! 
By the time I’d exchanged greetings with media members and had everything set up, the gates were open and people were pouring in. I decided to wade out into the already remarkable crowd to take some photos of the always-outstanding Kentucky Derby fashion.
Even before the first race began, Churchill Downs was packed; here’s jockey John Velazquez aboard Irish You Well in the paddock before the day’s opener at 10:30; you can’t even see his horse for the crowd surrounding the saddling area.

After taking in that scene, it was time me to seize the opportunity to snap some style photos. Of course, with this plan in mind the very first person I ran into had on the exact same dress as me.

We had a giggle fit and then posed for a photo together. She gets major points for the fabulous hat, but I think my photographer’s vest really completes the outfit, don’t you?
After that little bit of fun, I settled down to get photos of some of the style on parade at the Run for the Roses. From loud to lovely, there were some unforgettable looks at the Derby this year and I had a blast taking in the sights.

Once I was done with my junior varsity people watching, it was time to head to the big leagues of ogling: the Churchill Downs infield. The infield is where people go to lose their inhibitions, and I saw some truly remarkable individuals in there this year. A lot of people avoid the area, but I kind of revel in it; it’s the horse racing equivalent of letting your freak flag fly, and that’s right up my alley. 
The infield was definitely a popular destination and it was packed this year – which was hardly surprising considering that there was a record crowd of over 170,000 fans at the Kentucky Derby. 

While I saw so many interesting people during my infield adventure, and here are three of my personal favorites. I loved this guy, who I suspect may be from Maryland and who I hope to see again in two weeks at the Preakness: 

I loved these guys, who were willing to make an honest trade of labor for libations:

(It looks like it worked out, by the way, though I never actually saw them get on a horse.)

And this lady with the most spectacular hat I saw all day. Seriously: it was elaborate and huge and so detailed; she ended up taking photos with tons of people who were just as bowled over by her creation as I was. 

After my infield adventure, it was time for me to make tracks to the red carpet to check out what celebrities were in Louisville for the run for the roses. 
Now, I am no one’s stargazer; in fact, I’m notoriously bad at recognizing celebrities. I always just think they’re someone I’ve met before since they’re oddly familiar to me. Consequently have embarrassed myself rather spectacularly in the past: last year at Derby I passed by Bob Costas outside of the paddock. I sort of recognized him, didn’t want to be rude, turned around, gave him a big hug and asked how he’d been. He was confused/horrified, the NBC guys asked me to leave, and I fled at top speed blushing so brightly that I could probably be seen from space. In other words: I, unlike Bruno Mars, am nowhere near as smooth as a fresh jar of Skippy. 
So, there I was at the Kentucky Derby red carpet, reminding myself that I did not *actually* know any of these people. It … mostly went well. I was able to keep my trap shut around football players Matt Shaughnessy and Frostee Rucker of the Arizona Cardinals. 

I did just fine around Breaking Bad actor Dean Norris:

Same goes for seeing Lindsay Ellington, Gorgui Dieng, Paget Brewster, J.D. Shelburne, Vanessa and Nick Lachey, Luke Hancock, and Brian Vickers.

Then I stumbled: model, animal welfare advocate, FOX Sports host, NBA scout and horse racing fan Bonnie-Jill Laflin came down the carpet. See, she loves Thoroughbreds, and I’ve interacted with her before on Twitter through our America’s Best Racing account and in my head that meant we were friends. So as she walked past, I didn’t think twice and sang out, “Oh, hi, Bonnie-Jill!” She looked a little startled but smiled and said hi back. I took a photo and then booked it out of there; she was awesome but clearly the red carpet is a dangerous place for me. 

I decided my best bet after that was to take myself to my happy place: the racetrack. I’m so glad that I did, since it was time for the American Turf Stakes and one of my favorite trainers out there, Buff Bradley, won the race with his horse Divisidero. Buff is a fantastic, caring horseman and it tickles me pink every time he gets to the winner’s circle. When Divisidero returned to get his photo taken, Buff gave jockey Rafael Hernandez a big hug and Divisidero a giant pat on the neck. 

In fact, Buff loves his horses so much that he was wearing a tie bearing the likeness of his champion racemare (and mother-to-be in 2016!) Groupie Doll. That’s awesome.

The next race was the Humana Distaff, which is a very prestigious race for fillies and mares (female horses) 4 years of age and older. The race comes with a $300,000 purse attached and some of the finest older fillies and mares were lined up to duke it out for first place. I was rooting for my girl Judy the Beauty, who just tries her hardest every time she runs. She also constantly has her tongue hanging out of her mouth, which is pretty endearing.

And did she ever run her heart out in this race; you can see in the photo below that she almost got her nose (and tongue) in front, but a very game Dame Dorothy refused to give up. 

Jockey Javier Castellano gave a thumbs-up when he went into the winner’s circle, which I’m sure was reciprocated somewhere by Dame Dorothy’s owner, celebrity chef Bobby Flay. 

Because I believe in wearing out my shoes as much as possible when I’m at the track, my next stop was to climb all the way up to the roof to check out a race from there. It’s an amazing place to watch the action since you can see literally everything that’s happening anywhere on the grounds. 

That includes but is not limited to a man who looked like a combination of Abraham Lincoln and a hipster taking a selfie up there. 

Hope it came out well, No. 16! 
I also managed to shoot the finish of the next race, the Churchill Downs Distaff Turf Mile, while I was in my perch all the way above the rafters. That’s Tepin galloping to an easy win on the luscious lawn of the grass course. 

I then hustled back downstairs since I wanted to be on the track for the next race, which was the Churchill Downs Stakes. The reason I was so pumped was because Bayern, winner of the 2014 Breeders’ Cup Classic, was debuting for 2015 and I was dying to see how he did.

I was also excited to see my guy Private Zone; he’s a fixture in the winner’s circle at the New York tracks and I’ve developed a lot of respect and fondness for him. 

Well, it wasn’t Bayern’s day, but Private Zone just cruised, much to the delight of his team. That’s jockey Martin Pedroza celebrating as he crossed the finish line, and I was so delighted for Martin and everyone who works around this tough 6-year-old gelding. 

Time was really flying at this point, and before I knew it, it was time for the Woodford Reserve Turf Classic, the final race before the run for the roses. As the horses prepared to emerge onto the racetrack, I marveled at how packed Churchill Downs had grown in anticipation of America’s most famous horse race. 

The Woodford Reserve was a hard-fought battle between Finnegans Wake and Sky Captain, with Finnegans Wake (on the outside in the photo below) gutting it out to get his nose in front at the wire. 

Owner Jerry Crawford was clearly tickled with his horse’s performance, laughing delightedly with jockey Victor Espinoza after the win. 

Then it was time for the 141st running of the Kentucky Derby. Since there was a lot of time between the two races, I decided to experience something I’ve never done before: journey from the backstretch barn area to the saddling paddock with the Kentucky Derby contenders in what’s become known as the “walkover.” It was something I’ve always wanted to experience in person, and it was something I was so excited to share with you for my maiden voyage. 
As I was walking over to the barn area, I was struck by the sheer beauty of the afternoon and the stunning spectacle of the Churchill Downs complex, which was packed from the floor to the rafters. 

When I arrived at the backside (the racetrack name for the barn area) there were throngs of people lined up to catch a glimpse of the runners for the first leg of the Triple Crown.

I decided to wander around the stables and visit some of the Kentucky Derby contenders in the final moments before the biggest race of their lives.
Dubai invader Mubtaahij was looking very relaxed as he waited to make his American debut:

Ahmed Zayat, owner of American Pharoah and Mr. Z, looked nervous but excited and was surrounded by his family at trainer Bob Baffert’s barn.

Team Danzig Moon was having a great time, posing for photos with hand-made signs:

Then, suddenly, it was time for the horses to emerge and get ready for the walkover. They milled about on the backstretch, circling and waiting for the whole group of 18 Thoroughbreds and their human entourages to arrive for the march to the saddling paddock. 
Dortmund came out, followed by Danzig Moon: 

When American Pharoah arrived, I was so impressed by his beauty and calm demeanor.

Then, it was time for the walkover to begin! There was such a feeling of electric anticipation in the air as the Thoroughbreds, their handlers, their trainers and their owners took to the main track and set out for the twin spires of Churchill Downs.

As we passed fans heading around the turn, people stretched to see their favorite horses and get a photo or selfie.

For the most part, the horses were incredibly unfazed by the crowd and the noise; American Pharoah and Dortmund each seemed to be handling the scene with aplomb.

Once we got to the home stretch part of the track, I settled into my spot on the photo line to wait for the post parade and the singing of “My Old Kentucky Home.” I used the downtime to take some photos of the people in the stands there to watch America’s biggest horse race: 

I adored these guys, who came to the Derby in full regalia to support American Pharoah:

Gotta love it! 
Finally, it was time for the run for the roses. A deafening roar erupted from the crowd as 18 3-year-old Thoroughbreds catapulted out of the starting gate and into the home stretch for the first time as the Kentucky Derby began. 

That cacophony only grew louder as American Pharoah fended off Firing Line and Dortmund as he charged down the homestretch with incredible determination. 

Moments later, American Pharoah became a part of history as the 141st Kentucky Derby winner with his jockey Victor Espinoza raising his fist in celebration.

There was so much cheering in the crowd, but I think some of the loudest noise was coming from those Pharoah fans I’d spotted earlier: 

Congrats, guys! 
I then hustled over to the Kentucky Derby winner’s circle, which afforded amazing views of American Pharoah and Victor Espinoza returning to collect their congratulations. 

The famed red roses of the Kentucky Derby blanket were draped over American Pharoah’s neck, and then he and his humans posed to have their image immortalized in the annals of sports history.

Then it was time to present the famed solid-gold Kentucky Derby trophy; each of American Pharoah’s connections had the opportunity to hold the storied prize aloft: owner Ahmed Zayat, trainer Bob Baffert (who also held up four fingers, one for each of his Kentucky Derby wins) and jockey Victor Espinoza. 

Then things got kind of out of hand, but in the most fun way! Someone handed Victor a bottle of champagne, and he immediately popped the cork.

And then proceeded to completely douse the rest of his crew with the spray.

Well played, Victor. Well played. 
But perhaps my favorite moment of the weekend came next: an official whispered to Victor that the servicemen and women who stood guard over Churchill Downs all weekend had asked for a photo with him. Without wasting a moment for the stairs, Victor leapt over the railing of the trophy presentation platform and ran to join his waiting fans. 

And he didn’t just stand there and smile: he gave them the photo of a lifetime: 

It was the perfect end to an amazing Kentucky Derby, and we have so much to look forward to in the coming weeks as we get ready for the Preakness Stakes on May 16 at Pimlico Race Course. Thank you so much for joining me, and I’ll be back soon with all the dispatches from the second jewel of the Triple Crown!