Pink, Power & Prestige: The Legacy of the Kentucky Oaks at Churchill Downs
Today, May 2, 2025, marks one of the most anticipated events in American horse racing—the Kentucky Oaks at Churchill Downs in Louisville, Kentucky. Held each year on the Friday before the Kentucky Derby, the Oaks is more than just a prelude to the Derby—it’s a celebration of elegance, strength, and tradition, featuring the fastest three-year-old fillies (i.e. the young ladies) in the sport.
A Timeless Tradition Since 1875
The Kentucky Oaks has been part of Churchill Downs' history since the track first opened in 1875. Founded by Meriwether Lewis Clark Jr.—grandson of William Clark of Lewis and Clark fame—the Oaks was inspired by England’s Epsom Oaks and has remained a cornerstone of thoroughbred racing in the United States.
Originally run at a mile and a half, the race has been adjusted over time and is now set at 1 1/8 miles, testing not only a filly’s speed but her endurance. With a purse of $1.5 million, it's one of the most prestigious races for female horses on the calendar.
A Day Devoted to the Ladies—On and Off the Track
Nicknamed “Lilies for the Fillies,” the Oaks is famously symbolized by a beautiful blanket of stargazer lilies placed over the winning horse. The day is also a visual spectacle, as spectators show up in pink attire to support breast and ovarian cancer awareness through the event’s “Pink Out” theme.
From stylish hats to signature cocktails like the Oaks Lily, the Friday before the Derby has become a day of celebration that blends tradition with philanthropy, with proceeds benefiting women’s health initiatives across the region.
Memorable Moments Through the Years
The Kentucky Oaks has seen its share of incredible performances and emotional finishes. In 2009, racing fans witnessed Rachel Alexandra deliver a jaw-dropping 20 ¼-length victory—still the largest winning margin in the race’s history. In contrast, 2006 brought one of the biggest surprises when Lemons Forever crossed the finish line as a 47-1 longshot.
The race has also been a platform for trailblazing women in the sport. Jockey Rosie Napravnik made headlines by winning the Oaks twice, becoming a role model for young women aspiring to join the racing world.
2024 Recap: History Made Again
Last year’s race was unforgettable. Thorpedo Anna captured the Oaks title under trainer Ken McPeek and jockey Brian Hernandez Jr.—and the duo made headlines again by winning the Kentucky Derby the very next day with Mystik Dan. It marked the first time in over 70 years that a trainer and jockey team claimed victory in both races during the same weekend.
The Road to the Starting Gate
Entry into the Kentucky Oaks is earned, not given. Fillies must accumulate points through a series of prep races held across the country. Only the top contenders secure a spot in the starting gate on Oaks Day, ensuring a competitive and thrilling race for fans and bettors alike.
Representing The Agency in Style
We’re especially excited for this year’s Oaks because our very own Agency Real Estate Advisor and dear friend, Sara Huiss, and her husband Randy are attending the festivities in person today! From the fashion to the fanfare, we can’t wait to see the photos and hear all about their day at Churchill Downs. Sara and Randy, we’re all living vicariously through you—and truly wish we were there with you. Have an unforgettable time!
Why It’s More Than a Race
Whether you’re a lifelong fan of horse racing or attending for the atmosphere, the Kentucky Oaks is a must-see event. It combines high-stakes competition with heartfelt causes, dazzling fashion, and Southern charm. It’s a celebration of excellence, tradition, and community—and it all unfolds today at the iconic Churchill Downs.
So don your best pink outfit, pour yourself a chilled Oaks Lily, and cheer on these incredible athletes as they chase glory on one of the sport’s most legendary stages.
