Top 5 Famous Kentucky Derby Winners That Made History

Kentucky Derby

It has been called the most exciting two minutes in sports and is watched by millions worldwide every year. The Kentucky Derby, one-third of the American Triple Crown and one of the oldest horse races in the world will once again take place on the first weekend in May.

Featured Image: Richard HurtCC BY 2.0, via Wikimedia Commons

Kentucky Derby 2014 finish
The Kentucky Derby is one of the most prestigious horse races in the world. –
Bill Brine
CC BY 2.0, via Wikimedia Commons

Five of the Most Famous Kentucky Derby Winners in History

You may have already looked at the Bovada Kentucky Derby betting markets for the best value bets. But whichever runner and rider does end up draped in the traditional blanket of roses this year, will have to perform incredibly well to put themselves in the same conversation as our five of the most famous Kentucky Derby winners of all time.

Smarty Jones

It had been a long time coming, but in 2004 Smarty Jones became the first undefeated horse to win the Kentucky Derby since Seattle Slew in 1977. Jockey Stewart Elliott also made history by being the first rider to win the famous race on his very first attempt.

Smarty Jones was a huge fan favorite – and the one that all the sportsbooks agreed would probably win. But being the favorite and actually winning don’t always go hand in hand. It was a tough race, but Smarty Jones pulled through the field to eventually beat Lion Heart in a two-horse race to overwhelming adulation.


It was one of the most famous sports rivalries of the time – and in 1978, Affirmed beat Alydar to win the Kentucky Derby, eventually claiming the Triple Crown just a year after Seattle Slew had achieved the same record. Affirmed was only the 12th horse ever to win the prestigious title, and there was a 37-year wait for the next one.

In the Kentucky Derby, Affirmed had gone into the race as the second favorite behind Alydar. That was even though Affirmed had won three of the five races the two had competed up until that point. In the end, Affirmed won by just one and a half lengths and jockey Steve Cauthen also won the Sportsman of the Year award.


At 91-1, Donerail is still the biggest longshot ever to win the Kentucky Derby. It was back in 1913 when the thoroughbred stallion shocked everyone by claiming the prize, and that achievement was even greater as the horse and jockey had to walk three miles from their temporary stables before even starting the race.

It is not known how many people won big with those odds. But it would have been more than there ever had been before because of a change in betting laws that allowed for a smaller minimum stake. Donerail never hit those heights again – but the name lives on in Kentucky Derby history to this day.

Kentucky Derby 2009 3
Many of the famous winners made their move on the final turn. – from Lindenhurst, IL, USACC BY-SA 2.0, via Wikimedia Commons

Rich Strike

We don’t have to go quite as far back into history for our next memorable Kentucky Derby winner. Rich Strike won just last year – and at odds of 80-1, he was the second biggest longshot to claim the prize. But he nearly didn’t race at all, only coming in as a late replacement.

In one of the deepest fields ever, Rich Strike settled into the middle of the pack until making his move on the final turn. He was briefly boxed in by a tiring horse but pushed through on the inside of Epicenter to eventually cross the line first by just three-quarters of a length.


Those longshot winners will be remembered long after their victories. But the most famous name in the history of the Kentucky Derby is probably Secretariat. In fact, he is regarded as one of the greatest racehorses of all time after winning the Triple Crown in 1973.

That started with a record-breaking run in the Derby – a record that still stands today–a feat repeated in both the Preakness Stakes and the Belmont Stakes. His 31-length victory in that last race is considered one of the greatest races in history, but it all started at the Derby.

FAQs About Famous Kentucky Derby Winners

Who was the biggest longshot to win the Kentucky Derby?

Donerail, with odds of 91-1, remains the biggest longshot winner in the Kentucky Derby’s history.

Which famous horse still holds the record for the fastest Kentucky Derby time?

Secretariat, one of the greatest racehorses of all time, still holds the record for the fastest Kentucky Derby time.

How many horses have won the Triple Crown, including the Kentucky Derby?

As of September 2021, only 13 horses have won the prestigious Triple Crown, which includes the Kentucky Derby, Preakness Stakes, and Belmont Stakes.

Final Thoughts on Famous Kentucky Derby Winners

The Kentucky Derby has a rich history of thrilling performances and iconic champions. These five remarkable horses – Smarty Jones, Affirmed, Donerail, Rich Strike, and Secretariat – each left their indelible mark on this prestigious event. As we look forward to the next race, we celebrate these legendary Kentucky Derby winners’ incredible achievements and inspiring stories.

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Malcom Mott

Malcom is a student at Saginaw Valley University near Flint, Michigan. He is an avid writer and contributes to online media, and dabbles in using AI technologies to find new vegan recipes.

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