Memorable Moments From the Kentucky Derby

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A jockey on a racehorse.
BetMGM @BETMGM Jun 21, 2022, 9:45 AM

The main and final highlight of the two-week-long Kentucky Derby Festival, the Kentucky Derby, is a Grade I stakes race for thoroughbred horses with a history as exciting as it is extensive. It’s one of the most popular events for horse racing betting and online sports betting enthusiasts in the US and around the globe and takes place annually on the first Saturday of May (with a few exceptions.)

It’s safe to say that there have been many memorable moments – both good and bad – since the Kentucky Derby’s debut in 1875. Here is a round-up of the top five.

1. The very first Kentucky Derby

How could we neglect to mention the very first Kentucky Derby event, which set the scene for all other thrilling events to follow? Taking place on May 17, 1875, the race drew in a whopping 10,000 keen spectators and was a great success. The winner was a gorgeous chestnut-colored stallion called Aristides, ridden by American jockey Oliver Lewis. It’s reported that the dynamic duo beat out 14 other horses and won the then mile-and-a-half race by two lengths. 

Fast fact: Did you know that the length of the race remained a mile and a half until 1896 when it was permanently changed to a mile and a quarter? 

2. Shoemaker’s big mistake

The 1957 Kentucky Derby goes down in the history books as one of the most nerve-wracking and dramatic races ever and is often referred to as horse racing’s version of basketball’s “Shot Heard Round the World.” Most bets were on Bill Shoemaker and his horse Gallant Man to snag the win, and that seemed like it was going to happen until the last few seconds of the race when Shoemaker stood up to celebrate his victory a tad too early at the 16th pole. Unfortunately, his jubilation caused Gallant Man to slow down considerably, allowing Willie Hartack and Iron Liege to steal the lead and win by a nose.

3. Secretariat secures his win

Anybody who knows anything about Kentucky Derby horses, and race horses in general, will have heard the name Secretariat mentioned more than a few times. Arguably the greatest racehorse of all time who won all but one of his lifetime races, this beautiful reddish-brown stallion, nicknamed “Big Red,” secured his anticipated win at the Kentucky Derby in 1973. 

The race was a heart-thumping one, with another horse, Sham (who had beaten Secretariat just weeks before in the Wood Memorial,) taking the lead until the finishing stretch when Big Red managed to pip him, reaching the finish line ahead of his rival by two and a half lengths. His winning time of 1:59.40 set a new record, which is still unbroken to this day. Just to add to his impressive performance, Secretariat went on to win the Preakness Stakes just a fortnight later.

4. Donerail gets it done

Donerail, a bay-colored colt ridden by Roscoe Goose at the 1913 Kentucky Derby, is known for being the most notorious longshot victory in the Derby’s history. The horse racing odds were 91–1, so it goes without saying that this was a win nobody expected. Add to the odds the fact that, due to overcrowding at the stables, Donerail had to trot three miles to Churchill Downs from Douglas Park right before the race, and it’s easy to see why fans still talk about this lucky stallion many, many years later. Another kicker? Donerail clocked in at 2:04.80, setting a new record at the time.

5. The “Fighting Finish”

Everyone attends the Kentucky Derby to see the horses battle it out, but few expect to see the jockeys getting physically competitive too! During the 1933 Derby, jockeys Herb Fisher and Donald Meade (who was also known as the “bad boy” of racing due to his many suspensions throughout his career) let the excitement and their ambition get the better of them. 

As the two riders neared the end of the race, Fisher and his horse Head Play were in the lead. With seconds to spare, Meade and Brokers Tip pulled forward, with both horses now running head-to-head. This was when the jockeys started tussling, grabbing hold of and whipping one another. The race ended with Meade’s Brokers Tip winning by a nose. But the trophy wasn’t the only thing Meade walked away with that day. Both Meade and Fisher were slapped with a 30-day suspension and bad reputations. 

Until his dying day in 1983, Fisher insisted he’d been cheated out of a win. Horse racing fans are torn regarding the outcome of the race, with some siding with Meade and others backing up Fisher’s claims that it was he who was subjected to foul play and was simply defending himself in the moment.

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Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.

Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.