Every time May rolls around each year, the Bluegrass gets a glow-up. Greater Louisville is flooded with visitors, many of them celebrities, to attend the Kentucky Derby and hit the red carpet at the Barnstable Brown Gala. Suddenly, everyone wants to be from Kentucky; gone are the hillbilly references and mountain folk tropes.  One of my favorite parts of the Derby is watching the rich and famous struggle through “My Old Kentucky Home” even though the lyrics scroll across multiple screens.  Most of them have a Mint Julep in hand and claim to love it. I don’t bet on the ponies, but I’d wager they really don’t like minty-fresh bourbon at any other time of the year. 

Unfortunately, in recent years these temporary Kentuckians have discovered the Kentucky Oaks, a fillies-only stakes race run the Friday before the Derby.  The Oaks used to feel like the secret race for Kentucky folks only, but, no more. Maybe it’s because the official beverage, the Oaks Lily,  is a delightful alternative to bourbon mouthwash. 

On Derby Day proper,  both outsiders and insiders work pretty feverishly to outdo one another.  They crave the attention of retired Olympic skaters-turned-Derby-fashion-commentators with their elaborate hats and fascinators.  Some of the best I’ve seen are homemade designs, loaded with roses and plastic horses, decidedly not couture but fabulous, nonetheless.  Probably the best part about that sacred Saturday for the true Kentuckians is that we can claim the Derby, giving us a day of endless clout over the year-round influencers.

Let me explain my Derby nostalgia: I was born in Louisville (so I pronounce it correctly), but when my parents parted ways, my mother, brother and I settled in Florence. The agreement was that my brother and I would spend alternating weekends in Louisville with my father, and occasionally these visits fell on the first weekend in May. The first time this occurred, I was about four or five years old and as a special treat, we got dressed up and headed to Churchill Downs.

As my father often told it, a photographer from Life magazine was taking “society” shots at Churchill Downs and asked if he could take my picture. My dad was so proud; his darling little girl in her pink dress was always willing to smile, a performer from day one.  He had given me the nickname, Happy Hillary, when I was a baby, because it was easy to get a grin from me. The photographer did not witness the legendary happiness; I was not terribly cooperative and refused to smile. I hid behind boxwoods, made faces and pouted. My fifteen minutes of fame ended in about five. To commemorate my bad behavior, my dad took his own snapshot of my foul mood.

I can’t blame him for assuming I would be happy to pose, after all, my own mother was on the Royal Court of the Derby Festival her freshman year at the University of Kentucky. Unlike her ill-tempered offspring, Mom posed and smiled like a true Queen, yet she lost the crown to Martha Layne Hall (later Collins) who went on to become Kentucky’s first and only female governor.  I like to tease that my mom’s career in politics ended with that pageant.  In terms of my own lost moment of Derby fame, I may have inherited my mom’s smile, but not her obliging, beauty-queen demeanor.

An important detail left out of my Derby ramblings thus far is that the Derby is actually a horse race.  This brings me to our best chance at Derby and horseracing bragging rights here in Boone County. In 1978, 18-year-old jockey from Walton, Steve Cauthen, won the coveted Triple Crown astride Affirmed. This rare achievement is earned through a win at the Kentucky Derby, followed by the Preakness Stake and the Belmont Stakes.  There have been thirteen Triple Crown winners in history. Affirmed held the Triple Crown title until 2015, when American Pharaoh became the next to take all three wins. Steve Cauthen retired at the age of 32, after winning many championships across England and Europe.  He still lives in Boone County.

Several years before Cauthen guided Affirmed to victory, Virginia-born thoroughbred, Secretariat, won the Triple Crown in spectacular fashion.  His times set records still unbroken, among them his 31-length win at the Belmont Stakes, the final of the Triple Crown races. He was a large, powerfully built horse, standing over 16-hands high, earning every bit of his nickname, Big Red.  By all accounts, he had perfect confirmation meeting every requirement of his sport, which was apparent during the height of his career.  Secretariat retired to the legendary Claiborne Farm in Paris, KY, where he became the sire to over 600 foals.

My grandmother had a friend with an inside connection at Claiborne Farm who was able to get us a private introduction to Secretariat several years before his death in 1989.  Though I had plenty of exposure to horses growing up, he was an intimidating animal. The man who gave us the tour set the tone, telling my brother and I that we’d better be careful around the champion Thoroughbred, hinting he might try to bite us.  Though his size was undeniable, he wasn’t aggressive. Later, my brother and I agreed that our tour guide was a little scarier than Big Red.

May is upon us and this year marks 150 years of the Kentucky Derby. So memorize your lyrics, decorate a hat, pour a traditional drink and enjoy Kentucky’s most celebrated holiday, no matter where you’re from.