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Can a Horse Run in the Kentucky Derby Twice?

The Kentucky Derby, known as the Run for the Roses, is one of the most famous horse races. The one and a quarter-mile of purse speed is often referred to as “the most exciting two minutes in sports.” Limited to only twenty horses, it is natural to wonder: Can a horse run in the Kentucky Derby Twice?

A horse cannot run in the Kentucky Derby twice. The reason a horse can’t run in the Kentucky Derby twice is that the race is limited to three-year-old horses only. There is no limit, however, on how often a jockey can ride in the derby.

Even if you have never followed horse racing, it would be hard to have never heard of the Kentucky Derby. From the roses to the mint juleps, the race is full of tradition. Even fashionistas look forward to it: it’s all about the hats. But how did the race get its start? And why do the horses have to be three years old?

The Kentucky Derby: A Race of Tradition or Money

Tradition. That’s what anyone says when somebody asks a question about The Kentucky Derby that nobody knows the answer to: Its tradition. Even the reason why only three-year-olds can enter the derby is unknown. Its tradition. However, there is a theory, and it has to do with the short careers of racehorses.

Why Are Race Horses So Young?

Racehorses have short careers. They start young, some as early as two years old, and generally don’t race beyond eight. The reason for this is speed and cartilage.

Horses grow until they are about six-years-old, until then, not all the cartilage in their bones has fused. Before race trainers can even begin to think about putting a person on a horse’s back, the cartilage in the knees of the young horse has to have fused. This natural process happens between 18-24 months old.

After the cartilage has fused in the knees, the clock begins ticking as horses reach their peak speed between 3.5 to 4.5 years of age. By the time a horse reaches five, it is starting to slow. Thus, a horse’s top speed window is short, despite horses having an average life span of 25 – 30 years.

Theory on Why Horses Are Three at the Kentucky Derby

Thus, the theory on why horses are three at the Kentucky Derby is money. Horse racing is big money business, and if a horse does well at three, doors open, including in breeding. Making babies is where real money can be made. This is why winners of The Kentucky Derby (which is part of the coveted Triple Crown of races) are often retired before reaching four years old. Winners fetch the highest breeding fees—some winners earning their owners 80 million in a year.

How Horses Get Selected: The Road to the Kentucky Derby

Only twenty horses race in The Kentucky Derby. The number has fluctuated slightly during the race’s history, but since 1975 it has been held to twenty. Horses’ names are not pulled from a hat. There is a system, and it is called The Road to the Kentucky Derby.

The Road to The Kentucky Derby

The Road to the Kentucky Derby is actually roads, plural, and replaced a point and ranking system that previously determined who made it to the big race. Now there are three pre-derby racing schedules for the United States, Europe, and Japan. Horses are entered in these races and earn points, depending on how they do. It is these scores that determine who gets to race.

You can see the 2020/21 schedule here.

The Kentucky Derby: Mint Julep and Hats

Tradition. The Kentucky Derby is full of it. Two of the best-known traditions are the mint julep and hats.

Why Mint Julep is the Drink of The Kentucky Derby

Take bourbon and combine it with crushed ice, sugar, and mint. Bourbon, itself, is a very Southern beverage. But the drink truly became part of the Derby fabric in the late 1930s after Churchill Downs began serving the drink in special Derby souvenir cups. 

In 2021 there were 11 gold-plated julep cups for sale at 2,500 dollars (numbered 1-11) and 89 silver-plated cups for 1,000 dollars (numbered 12 – 100). The 2021 recipe, however, was released to the public to make at home, and you can read it by clicking here.

Why There Are so Many Hats at the Kentucky Derby

Southern culture in the United States has always involved hats, especially during the times when The Kentucky Derby began. However, the root of it being a true Derby tradition is jolly old England.

Mary and her husband, Colonel Meriwether Lewis Clark Jr, went to England and France in the run-up to the first-ever Derby race. The couple enjoyed the racing fashions at these European races, which were and still are, full of hats.

Upon the couple’s return, as Meriwether helped to establish the Derby, Mary used her high influence to encourage women to treat The Kentucky Derby as a high fashion event. Women did, complete with hats, as Mary so desired. While the fashions in the stands have evolved over the years, the hat remains an essential part of the outfit. 

10 Kentucky Derby Fun Facts

  1. 1875 was The Kentucky Derby’s first run, making it the youngest Triple Crown race. (source)
  2. While the Kentucky Derby is often referred to as “the most exciting two minutes in sports,” only two horses have ever completed the race under the two-minute mark. These horses are Secretariat, who finished 1:59 2/5 in 1973, and Monarchos 1:59.97 in 2001. (source)
  3. The most a jockey has ever won the Kentucky Derby is five times. The record is held by two jockeys: Eddie Arcaro “The Master” and Bill Hartack. (source)
  4. Bill Shoemaker is the oldest jockey ever to win The Kentucky Derby. He won in 1986 at the age of 54, riding Ferdinand. (source)
  5. The Kentucky Derby’s nickname is the “Run for the Roses.” The nickname comes from the 40-pound (18 kg) garland placed over the horse, made from over 400 roses. (source)
  6. Fillies have only won The Kentucky Derby three times: Regret (1915), Genuine Risk (1980), and Winning Colors (1988). Interestingly, this isn’t because fillies are slower than colts, but due to how horses earn points and, of course, there is controversy around the matter. (source)
  7. 2.4 million is the biggest bet made in The Kentucky Derby. It was made in 2021 by Jim “Mattress Mack” McIngvale on the horse Essential Quality. The bet was lost as the horse came in fourth. (source)
  8. Horses in The Kentucky Derby share the same birthday. This is because all Thoroughbred horses in the Northern Hemisphere are given the birthday of January 1st, and Southern Hemisphere Thoroughbreds are given August 1st. These dates are during each hemisphere’s breeding season. (source)
  9. Donerail is the longest long shot winner in the history of The Kentucky Derby. In 1913 Donerail had been given a 91- shot of winning. That was good enough for him. (source)
  10. Ben Jones has trained six Kentucky Derby winners, more than any other trainer. (source)


The Kentucky Derby is a treasured race saturated in traditions. No horse can win it twice, and the restrictiveness of the three-year-old’s only rule goes hand-in-hand with their exclusive collectible mint julep cups and the high fashion it promotes.


Anrie Diedericks

I've been around horses since I was 6 years old and started competing at the age of 9. Horses are my greatest passion and I am thrilled to be able to share my 23 (and counting) years of experience and knowledge with you.

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