The fun in gambling lies in taking risks and defying the odds. The thrill of placing a bet on an underdog and witnessing them emerge victorious is unmatched. The Kentucky Derby has witnessed many memorable moments throughout its history, but few can compare to the incredible upsets of ’91-1, 80-1, and 50-1 odds.

Over the years, the rate of success in longshots has risen. This year a couple of horses have 50-1 odds. Within this herd, Sun Thunder and Raise Cain have the potential to win it all and become a part of history. Talking about history, let us look back at some of the spectacular longshot moments in the Kentucky Derby.

Unforgettable Moments in Kentucky Derby History

The last two decades have seen the biggest upsets in the history of the Kentucky Derby. There have been five biggest upsets so far that deserve our mention. All of these horses entered the racetrack with at least 50-1 odds. Mine that Bird had 50-1 odds when it started at the 2009 race. The magnificent horse covered twenty lengths and put another seven lengths between itself and the other contenders by the time the race ended. It had managed to set a record for the largest margin since 1946.

Another horse with 50-1 odds was Giacomo. The bettors had no faith in Giacomo because it won one out of seven races in 2005. Its performance helped the rider Jerry Moss earn a place in the Rock and Roll Hall of Fame the following year. According to BetFTW, “Moss named the horse after Sting’s son”. Next came a win that has gone down in history as the most controversial win in horse racing.

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A Memorable twist in Kentucky Derby history

In 2019, Maximum Security crossed the finish line first in the Kentucky Derby but was disqualified for interference. The first runner-up, Country House, became the winner. This was the first time that a winner was disqualified for wrongful interference. Country House was suffering from an ailment and had 65-1 odds. This was the last match in the horse’s life. In 2022, there was once again a twist of fate in the Kentucky Derby. Rich Strike had 80-1 odds, but it blazed through the race course ahead of all.

Read More: Controversies in the Kentucky Derby – Events That Put a Shadow on the Biggest Horse Race of the Year

What was interesting was that Rich Strike was not supposed to race in the Derby. It got the opportunity when Ethereal Road pulled out of the race. Lastly, the horse with the biggest longshots was Donerail. In 1913, this horse had 91-1 odds when it entered the racecourse. That meant a bettor would get about $185 back for a $2 bet. From what we have seen so far, it would be folly to underestimate the underdogs in the Kentucky Derby.

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