Top 5 Kentucky Derby Fails in History

These champion racehorses seemed like a lock for the Derby win… until they picked the most important race of their life to run their worst race ever. Heather Benson counts ’em down.

It’s that time of the year when everyone sees a fast 3-year-old colt or filly running and declares “There’s is the NEXT Kentucky Derby winner!” Of course, anyone who spends any time around horses knows that a LOT can happen in four short weeks (heck, between the hour you unload at the show and your first class!) and that much like meteorologists predicting the weather, predicting a horse’s performance is a crapshoot at best. Hype tends to slam into reality on the first Saturday in May and one bad day at the track can mean the difference between destiny and destitution. And so we present some of the biggest fails in Kentucky Derby history:

#5: Himyar — 1878 Kentucky Derby

Himyar (photo courtesy of

(Photo courtesy of

Sure, it was 1878 and the Kentucky Derby wasn’t even a big deal yet, but Himyar still managed to catch the attention of the nation after a series of scintillating wins at age 2. He went into the Derby as the shortest priced favorite (1-4 odds) in history and lost by two lengths to Day Star. He did make up for in a way, by siring 1898 Kentucky Derby winner Plaudit.

#4: Native Dancer — 1953 Kentucky Derby

Native Dancer (photo courtesy of

Native Dancer
(Photo courtesy of

The “Grey Ghost” was undefeated in nine races at age 2 and crowned Champion 2-Year-Old Colt in 1953, with many viewing him as the Horse of the Year as well. He was just as sparkling at 3 and went into the Kentucky Derby still undefeated. As it happened, that Derby would be the only race he ever lost after being fouled twice during the race and losing by a narrow margin to victor Dark Star.

#3: Arazi — 1992 Kentucky Derby

Arazi (photo courtesy of

(Photo courtesy of

During the 1991 Breeder’s Cup Juvenile, held that year at Churchill Downs, Arazi had put on a performance that made him look like the second coming of Secretariat. Shipped back to his native France to condition for the following year’s American classic, he underwent a minor surgery and never again showed the same sparkle, despite the public still favoring overwhelming to win. He placed 8th behind Lil E Tee.

#2. Holy Bull-1994 Kentucky Derby

Holy Bull (photo courtesy of

Holy Bull
(Photo courtesy of

Holy Bull had it all going for him in the spring of 1994; he rattled off victories in the Florida Derby and the Blue Grass Stakes and seemed the closet thing to a sure thing. As it happened, the Kentucky Derby would be the only bad race he had that year, placing 12th of 14. He got white hot after that, winning the prestigious Met Mile and Travers Stakes before being named Horse of the Year over the eventual Kentucky Derby winner Go For Gin.

#1. Friesan Fire — 2009 Kentucky Derby

Friesan Fire (photo courtesy of

Friesan Fire
(Photo courtesy of

He may not have the household name status as some of the other Derby fails, but his Derby failure wasn’t pretty. After wins in the entire 3-year-old stakes series at the Fairgrounds Race Course, including the Grade I Louisiana Derby, he was on the board as the Derby favorite. Not only did he manage to lose and place nearly last, he lost to 50-1 longshot Mine That Bird. Double fail!

Go Riding.

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