The Greatest Moments in Kentucky Derby History

The prime jewel in the Triple Crown, a celebrated U.S. horse racing series, the Kentucky Derby has a tremendous attendance and online betting volume. Over its long and vibrant history, the seminal race has produced plenty of memorable moments. Let’s recall the most precious ones!

Early Legendary Moments in the Kentucky Derby

Horse racing bettors and non-gambler enthusiasts of the sport follow the Derby en masse for a bunch of good reasons. The thoroughbred race held in Kentucky is rightfully dubbed “The Greatest Two Minutes in Sports” for delivering an unforgettable experience in just two minutes.

Every year, thrill seekers have an exciting opportunity to watch the fastest runners and most skilful riders in the United States. In addition, the Derby attracts with its whopping purse and enchanting traditions. Below are summarized the key features and conditions of the race.

Venue Churchill Downs, Louisville, Kentucky, the U.S.A.
TimeAnnually in May
Distance1 ¼ miles or 10 furlongs or 2,012 meters
Track surfaceDirt
Eligible horses3-year-old male and female thoroughbreds 
Prize money$5,000,000

“The Run for the Roses,” as it’s also nicknamed after the winner’s floral garland, is a must-try for gamblers. With decent odds and successful picks, the race can yield excellent profits. The best Indian horse race odds are offered at 1xBet, the top website for online horse racing betting.

The Derby is America’s longest-running sports competition that has been held year after year without any intervals or cancellations since its inauguration in 1875. Let’s go back in time to the very first edition to review the highlights of the iconic horse race from the beginning.  

The First Kentucky Derby (1875)

Colonel Meriwether Lewis Clark Jr., an American entrepreneur and horse racing pioneer, became a founding father of the Kentucky Derby. The businessman was inspired by the finest English and French equestrian competitions he had seen during his European trips. 

In 1874, Clark launched the Louisville Jockey Club and laid the foundation for the Churchill Downs racetrack, which hosted the inaugural Derby only a year later. Participants ran a longer distance for the first and next 20 years: 2,400 meters instead of 2,000 meters.    

Aristides Wins the Inaugural Race

About 10,000 spectators witnessed the debut run in the grandstands on May 17, 1875. Jockey Oliver Lewis and racehorse Aristides etched their names into the history of the Kentucky Derby and entire American horse racing by finishing first and leaving 14 other competitors behind.

Lewis and Aristides’ performance was record-breaking for the 2.4 km distance in the United States. The remarkable duo came second the same year at another Triple Crown jewel, the Belmont Stakes. Here are some more details about the inaugural race and its winners:

TrainerAnsel Williamson
OwnerHenry Price McGrath
Time2:37.75
Prize money$2,850

Unforgettable Wins of the 20th Century

The 20th century marked the flourishing of the Kentucky Derby, and the credit is due to the racetrack’s new vice president, Colonel Martin J. “Matt” Winn. An astute manager and marketer, Matt Winn turned the Derby into an extremely profitable, popular, and prestigious horse race. 

While bringing in sizeable profits and crowds of attendees, the Run for the Roses provided a slew of never-to-be-forgotten victories throughout the 1900s. Below, we look back at the most salient wins of the 20th century in chronological order.

  • 1914: Old Rosebud, the odds-on favorite, won the race by eight lengths, setting a new time record on the track that remained unbroken for the next 16 years.
  • 1915: Filly Regret won the 41st edition and became the first female horse winner of the Derby, which raised the event to a higher level of popularity and prestige.
  • 1919: Not only did Sir Barton come first in the Kentucky Derby, but he also completed a hat-trick by winning the Preakness Stakes and the Belmont Stakes the same year.
  • 1932: Initially a longshot, Burgoo King pulled out a win by three lengths and became the first winner in the Derby’s history to be awarded a garland of roses.
  • 1973: Secretariat started last and finished first at a record 1:59.40, securing the title of fastest racehorse with the track record unbeaten up to now. 

Close Finishes and Surprising Upsets

The Kentucky Derby has always brought together contestants with outstanding abilities and lightning speeds. So, it’s no wonder the race frequently ends with a close finish and an unpredictable outcome. Here are some of the runnings with last-minute upsets.   

  • 1904: Elwood’s historic victory was a large upset at Churchill Downs. At odds of 15 to 1, the stallion who came to the race from California won its 30th edition, earning $4,850 in prize money. Most notably, Elwood was the first winner with a female breeder and owner.
  • 1913: Donerail is the Derby’s all-time biggest longshot winner with the unthinkable 91/1 odds. While approaching the finish line, he took the lead and pulled off an incredible upset win with a record-breaking time, paying out $184.90 for a 2-dollar winning bet. 
  • 1933: The 59th Derby was a breath-taking neck-to-neck race with two strong contenders, Brokers Tip and Head Play, where the former won by a nose. Riders pulled and pushed each other all along the stretch and continued fighting in the jockey’s room.  
  • 1957: In addition to supreme runners, the 83rd event is notorious for one of the closest finishes and unexpected outcomes of the Derby. Iron Liege snatched a nose victory from Gallant Man, whose jockey frustratingly lost the edge by misjudging the finish line.   

Iconic Horses and Their Legacy

We’ve already mentioned Secretariat, an unsurpassed record holder and a true legend of the Kentucky Derby and the Triple Crown alike, who won the whole series with record-breaking results in 1973. He also became the first animal to be a Kentucky Athletic Hall of Famer.  

Considered by many the greatest of all in the United States and globally, Secretariat left an impressive legacy. Among his numerous offspring are champion racers, including the winners of the Preakness Stakes, the Melbourne Cup, the Pacific Classic Stakes, and others. 

Another equine icon, Seattle Slew, is the 1977 triumphant of the Derby and two more Triple Crown events. His son Swale and descendants, California Chrome and Justify, repeated their sire’s feat at Churchill Downs in 1984, 2014, and 2018, respectively. 

Northern Dancer is an iconic horse and the first Derby winner bred in Canada. In 1964, he set the track record, later broken by Secretariat. Dancer is renowned for his champion progeny, the latest of which is Mystik Dan, who pulled out a win at the Run for the Roses in 2024.    

Legendary Jockey Performances

Unlike runners, who can only participate in the Kentucky Derby once in a lifetime, riders are allowed to enter the competition multiple times. As a result, brilliant jockeys and American horse racing celebrities Eddie Arcaro and Bill Hartack won the race 5 times each in different years.

Mike Smith won the competition twice but leads the field with 28 mounts. In 2005, he rode Giacomo to a win at odds of 50/1. In 2018, a 52-year-old Smith aboard Justify came first in the entire Triple Crown series and became the oldest rider to achieve the treble. 

However, a jockey’s performance doesn’t have to be a winning one to be legendary. Thus, Diane Crump made history by becoming the first woman to compete at Churchill Downs in 1970. She placed 15th out of 18 contenders and paved the way for female jockeys.  

Memorable Moments in Modern History

Although today’s Derby is visually a far cry from what it was a century and a half ago, the thrill and excitement of the competition remain intact. The running’s modern history is just as enthralling and full of indelible moments, some of which we recall below.

  • 2009: The 135th Derby is well-remembered by a jaw-dropping twist by runner Mine That Bird. Only 200 meters before the finish line, the 50/1 longshot gained the lead in a flash and won the race by 6 ¾ lengths, the longest margin since 1946. 
  • 2015: American Pharoah triumphed at the 141st race and also won the Triple Crown, which hadn’t had a winner in 30 years. The edition set an attendance record of 175,513 visitors and a betting record of nearly $138 million.
  • 2022: The 148th horse racing event had two odds-on favorites, and none met the expectations. Rich Strike, a complete outsider with odds of 80/1, came out of the blue and pulled out the Derby’s second-biggest upset victory.  

The Greatest Rivalries and Drama

With a premier field of contenders, the race inevitably produces fierce rivalries and dramatic denouements. And this is what makes the competition a magnetic spectacle, drawing many thousands of visitors and viewers. Let’s look back at the momentous battles at Churchill Downs.

  • 1978: The 104th race featured two favorites and long-time rivals, Affirmed and Alydar. Despite shorter odds, Alydar lost to Affirmed by 1.5 lengths in a close contest. The drama intensified when Affirmed defeated Alydar in the rest of the Triple Crown events.      
  • 1990: Long-standing adversaries, Unbridled and Summer Squall, met at the 116th Derby. Summer Squall had better odds, but Unbridled gained the upper hand in the home stretch. Summer Squall beat his rival at the Preakness Stakes the same year.
  • 2019: The dramatic 145th race started without much surprise when Maximum Security took the lead and eventually came in first. Yet, the result was disputed, Maximum Security was disqualified, and the win was awarded to the 65/1 longshot Country House.  

Off-Track Stories that Became Legendary

Regulars at Churchill Downs and the sport’s fans cherish memories of striking moments both on and off the track. Many funny, touching, and heartbreaking things happen in the stands and outside the racecourse. Here are just a few memorable stories that took place off the track.

  • 1980: The broadcaster ABC turned to singer Dan Fogelberg and asked him to write a song for the TV broadcast of the 106th race edition. It took Fogelberg a couple of days to compose “Run for the Roses,” which has become the Derby’s unofficial anthem. 
  • 1990: When Unbridled was making his winning run, his 92-year-old owner, Mrs Frances Genter, could not see her horse’s feat from the stands due to poor eyesight. Carl Nafzger, Unbridled’s trainer, gave her a highly emotional race call that was televised.
  • 2006: Barbaro won the 132nd Derby by an amazing 6.5 lengths. He was up to the Triple Crown title when he got a disastrous injury at the Preakness Stakes, finally leading to euthanasia. Since 2009, the Barbaro statue has greeted visitors to Churchill Downs.  

Conclusion

The Kentucky Derby is an unmissable sporting event with 150 thrilling iterations that stands out for the fastest runners, the most intense rivalries, and dramatic upshots. In addition to the great show, the Derby offers an exceptional chance to bet on horse racing online at a profit. 

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