Visiting Louisville, Kentucky, is always a vibe. Visiting it during Derby weekend? Now that’s an experience.
This “Rich Auntie” adventure began the moment I touched down at Muhammad Ali International Airport, because this city truly is about greatness.
Before I could even grab my bag, I was handed my first bourbon flight, courtesy of the Louisville Tourism Airport Welcome Center: three pours, from sweet and smooth to “sit down and respect your elders.”
But there was no time to linger, Derby Eve was calling. So I donned a fascinator, easily procured at a chic pop-up shop located in the lobby of the Hyatt Regency Louisville, and just like that, I was off to Churchill Downs.
Nestled inside the Club SI Suite & Enclosure (because Rich Auntie has to watch the races in style), I was surrounded by jockey silks and racing relics, and I couldn’t help but reflect on the Derby’s history.
In 1875, the very first Derby was dominated by Black jockeys. Oliver Lewis won aboard Aristide, and 13 of the 15 riders that day were African American. In fact, Black jockeys won 15 of the first 28 Derbies. And while they were eventually pushed aside due to discrimination, it can never be denied that Black horsemen built the foundation of the races.
While our presence since those early days has been rare, in 2024, at the momentous 150th Kentucky Derby, Larry Demeritte brought horse West Saratoga, proof that we are still very much in the race.
In the suite, Mint Juleps were flowing, and shrimp cocktail was in rotation, but I wasn’t the only one indulging. Five special guests — each with a very lucky plus one — had won an all-expenses-paid trip to the Kentucky Derby weekend courtesy Verizon Access, a rewards program that allows its customers to win exclusive experiences, from wine tastings with NBA greats to exclusive viewing of the world’s most exciting horse race, very “Rich Auntie” approved.
We all got to be a part of a Kentucky Oaks “first,” as the legendary run took place at night, with an 8:40 p.m. ET post time. That glorious win went to Always a Runner, who finished in 1:48.82.
But that was just the evening’s starting point. We were off to SI’s Revel At The Races With Tiesto, held at Ice House, a prominent event venue in Louisville. The night of merriment and music featured an impressive guest list that included Buffalo Bills cornerback Maxwell Hairston, Brazilian model Lias Ribeiro and her husband, former Chicago Bulls Joakim Noah, and many more.
The next day, back at Churchill, the energy shifted to bigger hats and even bigger bets. Inside the lounge, I caught up with CBS Mornings‘ Nate Burleson, along with Zay Flowers, who just signed another multi-million dollar contract with the Baltimore Ravens. So, of course, I had to know the secrets behind his Derby fit.
“I wanted to show where I’m from; make it a little streetwear and a little derby at the same time,” the Floridian native shared. “So I got the jean jacket, denim shirt with the tie, to make it a little classy and tie it in a little bit. Good pants. We picked this all out from YSL, two days before the race.”
Somewhere between several Mint Juleps, I placed my first bet on a horse named So Happy. Because at that point? I was.
My horse didn’t win, but history was made: Golden Tempo took the crown, making Cherie DeVaux the first female trainer to win in Derby history. Jockey Jose Ortiz secured back-to-back wins riding the top-placing horses in the Oaks and Derby.
With a whole night ahead of me, I decided to slip into something a little more reflective: a walk down Fourth Street. Music filled the open-air entertainment venue, but a deeper look reveals so much more. Civil Rights markers line the street, reminding you that this city, like so many, has a layered past.
Discrimination protests were held in the 1950s and 60s so segregated hotels like Seelbach and Brown would open their doors to all visitors. A less than 10-minute walk takes you to the Ohio River waterfront, where Black entrepreneur Shelton Morris founded a barbershop and bathhouse under the old Galt House in 1832. Not far from there, the Roots 101 African American Museum shares more of our stories so we can know and honor the city’s history and heritage.
And just like that, my Derby adventure crossed the finish line. And in true Rich Auntie fashion? I’m already shopping for my chapeau for the 153rd.