Top 5 most jaw-dropping moments in Kentucky Derby history

September 20, 2022

One reason people love watching sports, and why many choose to bet online on sporting events, is that you can never be certain what’s going to happen. A heart-stopping moment could happen at any time, and an upset is always on the cards, which is all part of the attraction of live sports.

The Kentucky Derby is a race that’s had its fair share of surprising moments. The race has been run since 1875 at Churchill Downs, Louisville, Kentucky, usually on the first Saturday of May. It is a beloved American institution, nicknamed “The Run for the Roses” because the winner is draped in a blanket of roses.

Here is our choice of the top 5 most jaw-dropping moments that the Kentucky Derby has seen over the years.

Maximum Security getting disqualified

In 2019 there was a lot of anger, disappointment, and confusion when Maximum Security was disqualified. He was running at odds of 9-2 and many were expecting him to win. True to form, he led the way round the first bend and held the lead by a length on the backstretch. He was, indeed, first over the finish line, with his owners jubilant in celebration.

But that jubilation was to be short lived. Two jockeys raised an objection. Apparently, Maximum Security swerved into another horse causing their jockey to pull back and avoid a collision. The objection was upheld, which meant that the horse that had come in second, a 65-to-1 underdog named Country House, was declared the winner.

The race footage seems to indicate that it was the horse himself who took the swerve as opposed to the jockey instructing him to swerve. However, the disqualification stood.

Seven Underdogs

 Longshots rule

The 1992 running of the Derby yielded surprising results. Every horse among the top seven finishers was an underdog and was expected to be nearer the back than the front of the race! It seemed as though the race had happened backwards, with none of the hot favorites performing well.

The winner was Lil E Tee who had odds of 17-1. No one expected this horse to come anywhere near first place – especially as his breeder had been told he’d never be a racehorse.

The favorite that day was Arazi with odds of 6-5, but he came in eighth ‒ the lowest placing ever for a Derby favorite.

A dog won the Derby

Well no, not really…

It was the 1913 Kentucky Derby and a jockey named Roscoe Goose claimed first prize on a “dog”. However, it wasn’t an actual dog but rather an absolute underdog of a horse. The odds were 91-1 and Donerail, a bay colt, had practically zero chance of winning.

Roscoe Goose was so proud to take part in the Derby as a born-and-bred native of Louisville that he didn’t really care which horse he rode. He was simply happy to be able to race. However, everyone was astonished when he took the lead and maintained it until the finish line.

Go for Gin wins

In the 1994 Derby, Go for Gin wasn’t a favorite. In fact, his odds were 9-1 – not terrible, but an unlikely winner. There were lots of faster horses in the field, so Go for Gin didn’t seem to be a contender for the podium.

1994’s Horse of the Year Holy Bull was the firm favorite at 8-5. However, there was a huge deluge just before the race that turned the usually firm track into a mushy mess. This meant that the race wouldn’t be about pure speed, but about focus and fortitude.

Go for Gin took the lead right from the start and stayed there all the way home!

 Iron Liege, 1957

In 1957, the Kentucky Derby saw one of its most dramatic finishes ever. On the finishing straight, Gallant Man had the slimmest of leads over Iron Liege. As they approached the finish line, with Iron Liege gaining, Gallant Man’s jockey Bill Shoemaker misjudged where the finish line was and stood up in the saddle to celebrate his “win”. However, he celebrated a fraction too early, giving Iron Liege the chance to sneak past and win the race.

As if the embarrassment of his error wasn’t bad enough, Shoemaker was suspended by the stewards for 15 days for “gross carelessness”. This mistake is considered to be one of racing history’s biggest blunders.

Final thoughts

So, there you have it, our top 5 most jaw-dropping moments in Kentucky Derby history. It really is the best two minutes of horse racing each year!

I admit I’m a history nerd, love learning stories of the past. Thank you for a great and insightful read…

Jon Parr (@JonParr21) View testimonials