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What are the greatest moments in Kentucky Derby history?

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80-1 underdog Rich Strike shocks Churchill Downs by winning the 148th Kentucky Derby after only being in the race due to a scratch.

The Kentucky Derby is one of the most loved sporting events in American history. What makes the running of 20 horses on the Churchill Downs track so beautiful? Its unpredictability is a huge part of the appeal.

Thoroughbreds have run for roses for 148 years, and every race bears no similarity to the last. A horse can only compete in the Derby once in its lifetime, meaning that no horse has ever raced in the Kentucky Derby more than one singular time.

Each Derby presents thrill and tradition to the nation, but some have gone down in history as unforgettable memories. As the 149th Kentucky Derby prepares to air on NBC and Peacock on May 6, take a look back to some of the infamous moments that will forever define the sheer splendor of the Kentucky Derby.

RELATED: How to watch, what to know for the Kentucky Derby 2023

1933: The Fighting Finish

Never before has the world seen a Run for the Roses quite like 1933, as fighting horses turned into fighting jockeys on the racetrack.

As the gates flew open for the 59th running, the horse Isiah grabbed the initial lead. It wasn’t until the third and final turn that budding star Head Play and jockey Herb Fisher roared with acceleration, breezing by the front runners into first position.

Just when Fisher felt that his horse had sealed the victory, however, he noticed jockey Don Meade and Broker’s Tip closing in from behind. Meade, dubbed the “Bad Boy” of horse racing by Time magazine, propelled forward to the side of Head Play. The horse responded, bumping into Broker’s Tip. This slight nudge, however, would cause an eruption.

Meade grabbed ahold of Fisher, pulling at him fiercely. Fisher pulled back, and the two were wrestling back and forth in hopes of knocking the other off his horse. As the finish line approached, both riders let go and slashed their whips.

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The two finished so closely together that no winner could initially be determined. After deliberation, however, Broker’s Tip was declared the winner by a mere nose.

Meade and Fisher engaged in another brawl in the jockey’s room after the race, and the two were handed 30-day suspensions as a result. While Broker’s Tip went down in history as the champion of the 59th running, the jostle of the jockeys was the lasting image in everyone’s minds in a race forever remembered as “The Fighting Finish.”

1957: The Standing Man

1957’s Run for the Roses not only featured one of history’s most elite fields of Thoroughbreds, but also one of the most dramatic finishes in horse racing history.

A group of the most esteemed horses met at Churchill Downs on the first Saturday of May, with hall of fame horse inductees Bold Ruler and Round Table lining up for race day.

The battle that ensued, however, was not dependent on those two horses. Rather, it was Gallant Man and Iron Leige who found themselves neck-and-neck when the finish line drew near. As the horses ferociously fought toward the race’s end, Gallant Man’s jockey, Bill Shoemaker, made a disastrous misjudgment.

Mistaking the sixteenth pole for the finish line, Shoemaker stood up to celebrate in victory before the race was actually over. Gallant Man pulled up and slowed down, allowing Iron Leige to surpass the leader for the Kentucky Derby crown by a simple nose.

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1973: World’s Fastest Horse

The fastest Derby time ever recorded was witnessed by a very lucky, then-record crowd of 134,476 at Churchill Downs in the 99th Run for the Roses.

While Secretariat was the morning-line favorite entering the race, many doubted that Big Red could pull off the victory after a third place finish at the Wood Memorial just two weeks prior.

As the gates opened, Secretariat’s rival, Sham, jumped out to lead the pack.

Sham held a steady lead for the majority of the thrilling contest, with most thinking that Secretariat would not be able to mount a comeback. Big Red, however, promptly narrowed the gap in the finishing stretch and surpassed the leader in the Derby’s final moments with a two and a half length win. Secretariat’s magnificent recorded time was a new world record.

The greatest horse of all time would go on to secure the first Triple Crown in 25 years, setting records in each of the three races that still remain to this day.

2006: Barbaro’s Legacy

As the 132nd Kentucky Derby approached, there was no clear-cut favorite in the field of 20, with the most competitive group of Thoroughbreds the Derby had seen in quite some time.

Brother Derek, who had won four straight races leading into the Run for the Roses, was declared the morning line favorite. Barbaro and jockey Edgar Prado, however, were a very close second, boasting an undefeated record.

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Barbaro intended to keep that streak intact. When the gates opened, however, Barbaro stumbled, bumping into both Bob and John. It took the Bay horse the majority of the race to make up ground, shocking the crowd and taking the lead with a quarter of a mile remaining.

Barbaro then pulled ahead significantly, claiming the Derby crown by 6 1/2 lengths over Bluegrass Cat. The horse became just the sixth to win the Derby with an undefeated record, capturing the gaze of the nation.

Now a fan favorite, Barbaro was expected to impress once again at the Preakness Stakes and claim the first Triple Crown accolade since 1978. These hopes, however, suddenly diminished as Barbaros shattered his leg in the race. The Thoroughbred’s will to continue inspired those across the world, but the injury would eventually lead to the horse’s passing on January 29, 2007.

2022: A Striking Victory

In the days leading up to the 2022 Kentucky Derby, all seemed to be unfolding as planned. Epicenter and Zandon were the objects of attention, expected to battle for the leading position and Derby title. Though both Thoroughbreds drew unfortunate post positions, it was not insurmountable for the elite competitors.

All would change the night before Derby Day, as it was announced that Ethereal Road was officially scratched from the Run for the Roses. The next horse up to take Ethereal Road’s 20 post position was Rich Strike, who bore a record of 1-0-3 in seven lifetime starts.

RELATED: Relive Rich Strike’s unbelievable upset victory

As 147,294 gathered at Churchill Downs, none had any idea what would transpire on the infamous track. Out of the gates, Summer is Tomorrow held the early advantage, setting a Derby record for fastest quarter-mile ran (21.78 seconds).

Messier managed to catch up and take top spot at the 3/4 mile mark, only for the favored Epicenter to swiftly surpass Messier at the head of the stretch. Rich Strike, who was sitting at the back in 15th, then pulled off a miraculous comeback. The horse impressively transitioned to the rail, dodging Messier and propelling past Epicenter in the final furlong to shock America.

Rich Strike and jockey Sonny Leon were just the second duo in Derby history to claim a win from the 20th post, and the victory was the first in any form of stakes race for Leon.

How to watch the 2023 Kentucky Derby:


  • Date: Saturday, May 6
  • Time: Live coverage begins at 12 PM ET
  • Where: Churchill Downs in Louisville, Kentucky
  • TV Network: NBC
  • Streaming: Peacock, NBCSports.com, NBC Sports app

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Watch the 149th running of the Kentucky Derby on Saturday, May 6 on NBC, NBCSports.com, the NBC Sports app and Peacock from 12 p.m. to 7:30 p.m. ET.