The Forgotten First to Win the Kentucky Derby
“The moment you know your history, is the moment they can no longer rewrite your destiny.”
In 1875, Oliver Lewis, a 19-year-old Black man born free in the heart of Kentucky, did something no one else had ever done, he became the first jockey to win the Kentucky Derby, a sporting event that would go on to define American tradition. But unlike the marble statues and glossy textbooks reserved for others, his story has been buried in silence.
Understand this. Thirteen out of fifteen jockeys in the first Derby were Black. The horse that crossed the finish line Aristide was trained by a Black man, Ansel Williamson. Black excellence wasn’t invited to the table. We built the table. We were the sport!
But why haven’t you heard this before?
Because when Black men and women win, systems move to erase the ink. When we rise, history finds ways to make us invisible. And yet, we are still here.
Oliver Lewis didn’t just race horses. He raced history. He rode against expectation. He rode with strategy. And when the plan changed mid-race, he adapted. That’s not luck. That’s leadership under pressure.
And though he never raced again in the Derby, his impact never left the track.
So what’s the lesson?
Know who you are before they tell you who you’re not.
Use every role even the overlooked ones to change the outcome.
Success isn’t just winning the race it’s knowing when to lead, when to adapt, and when to rise.
Your success exercise this week:
Write down three ways you’ve been conditioned to play small.
Now list three bold moves you will take this month to reverse that narrative.
Call it your “Aristide Plan.” Ride it like your name belongs in history too.
Just in case you didn't know The Aristide Plan is a 3-step blueprint to help you reclaim your power, shift your pace and win with purpose even when the odds are stacked against you.
Inspired by Oliver Lewis and his legendary ride on Aristide in 1875, this plan represents how to lead from the front, even when you were told to follow.
Step 1: Position Yourself With Purpose
Even if you're not the favorite. Even if you're underestimated. Lead from where you are. Step into roles that allow you to learn the terrain even if you're initially told to “just set the pace.”
Think about it, list 3 spaces where you're currently underutilised or overlooked. Now list one bold action to reposition yourself.
Step 2: Adjust in Real Time
When Chesapeake fell behind, Lewis didn’t panic. He didn't wait for permission, he moved. Winners don’t just follow the plan; they sense when it's time to shift.
How can you identify one plan in your life or business that’s no longer working. What would happen if you adjusted your pace or strategy today?
Step 3: Finish with Intention
Aristide pulled ahead not just with speed—but with timing, clarity, and execution. It's not about leading the whole race. It's about knowing when to move, when to rest, and when to rise.
Discover how to define your finish line. What does success look like—on your terms? Write it out. Make it real.
The Aristide Plan is your reminder that you don’t need anyone’s permission to shift from support act to legacy-maker. You just need clarity. Courage. And the will to ride your race.
Would you like this turned into a downloadable worksheet or graphic for your group?
That is why we honor Oliver Lewis not just for winning but for showing us how to win with dignity, under pressure and in full color.
This isn’t just history it’s inheritance. When we uncover the truth, we reclaim the ground we were never supposed to stand on. So let’s not keep Oliver Lewis’s legacy in silence. Pass it forward.
Start the conversation. Add your voice to the roll call of remembrance.
Drop a reflection below, send this post to someone raising the next generation of trailblazers, and make sure this name Oliver Lewis is never left out of the winner’s circle again.
