Horse Races And Tracks
Donerail, Kentucky Derby 1913

No Hopers who Won the Biggest Horse Race in America

Donerail, Kentucky Derby 1913
Rena Sherwood's image for:
"No Hopers who Won the Biggest Horse Race in America"
Caption: Donerail, Kentucky Derby 1913
Image by: Public Domain

It’s been called the greatest two minutes in sport. The pressure to win this race is so intense that even the most professional of jockeys can make the simplest of mistakes. Anything can happen in the Kentucky Derby and usually does. Here are the five biggest upsets in the race’s 135 plus years.

Dark Star (1953)

The 1953 Kentucky Derby was supposed to be a coronation for the sport’s biggest superstar of the 1950s – Native Dancer, nicknamed the Grey Ghost. In an age of black and white television, Native Dancer’s dappled grey coat made him a standout. Undefeated before the Derby, he was bet down to 3 to 5. Only ten other colts would dare to face Native Dancer. But the Grey Ghost could not catch the pacesetter, 25-1 longshot Dark Star, who won by a head.

This was the only race Native Dancer would ever lose. Although other horses would win at longer odds in the Derby’s history, this was the Derby’s biggest upset, the public was not expecting the champion’s loss. Native Dancer would win Horse of the Year twice and became a success at stud.

Exterminator (1918)

World War I decimated thoroughbred horse racing. Only ten colts and geldings could make the 1918 Kentucky Derby. When the heavy favorite, Sun Briar, was scratched due to an injury, the race was thought to go to heavy favorite War Cloud. The winner was Sun Briar’s stablemate, the chestnut gelding Exterminator, called the “Galloping Hatrack” due to his ugliness. He won on a muddy track at odds of 30-1.

Exterminator would go on to a spectacular racing career and became a national hero. He won at many different track conditions and lengths. However, he was the undisputed champion at long races a mile and a half or longer (which are not run today.) He was so dominant that the owner of Man o’ War refused to race his champion against Exterminator at long distances. The two champions never met.

Mine That Bird (2009)

Went off at odds of 50-1, the bay gelding was written off by the media, even though he was the two-year-old champion in Canada a year previously. He won by nearly seven lengths over 19 other colts and geldings on a sloppy track. His grandsire was the winner of the 1996 Kentucky Derby, Grindstone.  The Derby was the last race he would ever win.

Donerail (1913)

The biggest longshot ever to win the Run for the Roses was Donerail, who went off at 91 to 1. He was overlooked by the bettors and the media because of his poor races as a three year old before the Derby. He set a new track record for his dominating win. Not much is known about the bay colt by McGee – the same sire as Exterminator.  This hard working colt won 10 times in 62 starts.


More about this author: Rena Sherwood