A Look Back at The Kentucky Derby’s Most Memorable Winners

I know, I know, it’s only just February, but already, everybody in the horse racing world is looking forward to the first Saturday in May. Why? The Kentucky Derby. Each year, the Churchill Downs transforms into the beating heart of American horse racing.

This year’s Derby is already shaping up to be an exciting race. For many, part of the enjoyment is having a wager on the action and at the moment, there are some seriously good ante-post odds that are making online horse racing look an attractive avenue. Taking a glance at what’s available for online horse racing at Bovada ahead of time means you’ll definitely be able to secure a longer price – although do make sure that you’re confident the horse will actually run at this early stage. If you’re right about that, you could have your wager in early and enjoy some excellent pricing! It’s no wonder online horse racing is attracting so much attention even at this early stage.

Coming up are some horses who certainly made it to the starting gate and managed to rewrite history in the process. These horses tore up the script, shattered records, and straight-up refused to lose.

Secretariat (1973) – The Freak of Nature

There’s fast. Then there’s Secretariat. When Big Red exploded down the stretch in 1973, the clock nearly melted. His 1:59.40 remains the fastest Derby ever run, and the way he did it? Unbelievable. He started dead last. Then, with every quarter-mile, he ran faster – yeah, that’s not supposed to happen. Anyway, by the time he hit the homestretch, the others were too far behind to even claim to be ‘eating his dirt’! It truly isn’t hyperbole to say that this wasn’t just a win. It was a performance so ridiculous that I for one still watch the footage and shake my head in disbelief.

Mine That Bird (2009) – The 50-1 Shockwave

Calvin Borel and that blessed white rail. Can you name a more iconic duo? I certainly can’t.  Mine That Bird absolutely shouldn’t have won the 2009 Derby. He was 50-1, had no early speed, and was so overlooked that NBC’s race broadcast forgot to put his name on the screen during the stretch run – I’m not kidding! But, Borel rode him like he’d stolen him. It was like watching one jockey who’d been given a GPS for the shortest possible route. He snuck up that rail, leaving the entire field in a state of stunned disbelief. By the time anyone realized what was happening (including the commentators!), Mine That Bird was already six lengths clear and galloping his way into the history books.

American Pharoah (2015) – The End of the Drought

From 1978 to 2015, racing had a Triple Crown problem. That is to say that, nobody could win it! American Pharoah was different though. He didn’t just win the Derby – he made it look like a warm-up. Gliding over the Churchill Downs dirt like a horse born for the moment, he never looked in trouble. Some horses fight for the wire. Pharoah just took off, ears pricked, as if to say, “This? This is nothing.” It was the beginning of a history-making campaign, the kind racing fans had been waiting 37 years for. And when he sealed the Triple Crown five weeks later? The crowd roared watching him.

Rich Strike (2022) – The 80-1 Sneak Attack

You thought Mine That Bird was a long shot? Frankly, even getting into the 2022 Kentucky Derby was a long shot for Rich Strike! He simply wasn’t supposed to be there. In fact, he wasn’t even entered in the race until just one day before when another horse scratched. For his connections, that alone would probably have been a big enough moment. But, instead, it was just the beginning. Sitting in last place halfway through the race, Rich Strike looked pretty forgettable. But if you held your gaze on him for just one more second, you saw the pace pick up. He started weaving through the pack. By the time the leaders spotted him, it was too late. 80-1. The second-biggest upset in Derby history. 

Genuine Risk (1980) – The Filly Who Wouldn’t Back Down

Only three fillies have ever won the Kentucky Derby. Genuine Risk was the second, and for me, the toughest. Racing against colts? She didn’t care. A brutal pace? Didn’t faze her. When the field turned for home, Genuine Risk powered past the boys like she belonged – and she absolutely did. Then came the controversy. She finished second in both the Preakness and Belmont, but the latter came with a cloud of suspicion. She was cut off badly in the stretch – many say intentionally – but still managed to finish just a length behind. A different trip, and she might have been the first filly Triple Crown winner. Either way, she proved the Derby isn’t just for the boys.

War Admiral (1937) – The Silent Destroyer
When people think of War Admiral, they often think of his legendary match race against Seabiscuit – it was quite something. But before that, he was a Kentucky Derby champion. War Admiral looked nothing like a sprinter. He was too small, too refined, but he had an almost mechanical running style. To put it lightly, War Admiral was the opposite of his massive, long-striding father, Man o’ War. But what he lacked in size, (I know it’s a cliche) he made up for in heart. In the 1937 Derby, he set a blistering pace. Nobody ever came near him. He crossed the finish line without ever really being challenged.