Ranking the Biggest Disappointments in Kentucky Derby History

In horse racing, the only sure thing is that there is no sure thing. The average Kentucky Derby is run in about two minutes, and in that time, absolutely anything can happen. The race is not billed as the most exciting two minutes in sports for nothing.

Disappointment comes in many shapes and forms. It could be the heavy favorite like Point Given that simply could not lose…until he did. Or, it could be the narrow photo finish that went the wrong way. This year, Nyquist is heading into the Kentucky Derby undefeated and will try to emulate greats like Seattle Slew and Smarty Jones who kept their perfect record alive in the Derby. If he should lose on Saturday, it will be a major blow to his connections.

Here is a look at some of the biggest disappointments in Kentucky Derby history.

8. Native Dancer, 1953

Native Dancer broke from the starting gate in the 1953 Kentucky Derby at odds of 3-5, according to Daily Racing Form. The colt was not just a heavy favorite, he was awarded the title of Horse of the Year as a juvenile, which was a rare accolade.

Undefeated from nine starts as a juvenile, the massive gray colt kept his perfect streak intact heading into the Kentucky Derby and looked like a formidable threat. After a troubled trip, the best he could manage was a runner-up effort behind long shot Dark Star who pulled the upset at odds of 25-1.

Native Dancer went on to win the Preakness Stakes (Grade 1), as well as the Belmont Stakes (G1), and never lost again, completing his remarkable career with 21 victories from 22 starts.

7. Holy Bull, 1994

Churchill Downs is an interesting track. Though one of the country's most heralded and historic race tracks, the surface is one that horses tend to either love or hate. Holy Bull, for all of his talents, seemed to fall in the "hate it" category, at least that day.

After two impressive victories in the Florida Derby (G1) and the Blue Grass Stakes (G1), Holy Bull was tabbed as the heavy favorite in the 1994 Run for the Roses. The rain hammered Churchill Downs, leaving the track sloppy. Holy Bull never seemed to participate and finished a dismal 12th. He would go on to win his next six starts before being injured in his final race.

Though, his trainer speculated years later in Bill Christine's Los Angeles Times article that he was convinced his superstar horse's poor performance was because he was drugged. Disappointment, conspiracy and a beautiful gray horse—it was bigger than even Hollywood could dream up.

6. Bellamy Road, 2005

Bellamy Road did not have the sparkling record heading into the Kentucky Derby that many of his fellow disappointments on this list possessed, and he did not make amends with a stunning post-Derby career. However, his final prep race before the Kentucky Derby in 2005 was one of the single-most impressive performances by a three-year-old that decade.

He romped in the Wood Memorial (G1) by a dazzling 17 1/2 lengths, and in doing so, he was awarded a Beyer Speed Figure of 120—the highest ever recorded in a Kentucky Derby prep race. Off that impressive performance, coupled with an otherwise mediocre group of three-year-old rivals, he seemed like a strong contender in the Kentucky Derby. 

Unfortunately, his winning effort seemed to take more out of him than it appeared. He finished seventh as the favorite behind 50-1 long shot Giacomo, per Tom Keyser of the Baltimore Sun.

5. Unbridled's Song, 1996

Charlie Riedel/Associated Press

Unbridled's Song was from the first crop of the brilliant Kentucky Derby and Breeders' Cup Classic (G1) winner Unbridled. After winning the Breeders' Cup Juvenile (G1) in 1995, it was fitting that he would try to follow in his father's imposing footprints.

After a slow start to his three-year-old campaign, he appeared to hit his best stride later in the spring with back to back wins in both the Florida Derby (G1) and Wood Memorial (G1), two key prep races. He set the pace and ultimately could not sustain his speed for the 1 1/4 miles and wound up fifth. Unbridled was, however, represented in the winner's circle by a son—Grindstone. 

The race was a double whammy of disappointment. Cavonnier was on the losing end of the photo finish to Grindstone, and trainer Bob Baffert took the defeat to heart, telling Pat Ford of Yahoo Sports nearly two decades later that it was still the toughest loss of his career.

4. Empire Maker, 2003

Empire Maker had it all. He was a multi-generation blue blood with one of the most impressive pedigrees in recent memory, and he was trained by the great Robert Frankel. With those two factors alone, he was practically anointed as the Kentucky Derby winner at the start of his three-year-old season in 2004.

After back-to-back wins in the Florida Derby (G1) and the Wood Memorial (G1), the hype was so high around this colt that no one really noticed the game chestnut gelding that battled behind him in the Wood Memorial (G1). But that horse, a New York-bred from humble beginnings named Funny Cide, would turn the tables on him in the Kentucky Derby (G1). 

Empire Maker lost the battle in the Kentucky Derby, but he gets credit for winning the overall war. He denied Funny Cide the Triple Crown in the Belmont Stakes (G1) and has gone on to a prolific career in the breeding shed.

3. Arazi, 1992

Arazi was hailed as the second coming, and legendary announcer Tom Durkin christened him as a "superstar" in his call of the Breeders' Cup Juvenile (G1) the previous fall.

With international allure, the chestnut colt shipped to Churchill Downs for the Breeders' Cup after winning six straight races against top competition in Europe. In that race, he showed tremendous professionalism and extraordinary talent to win by an effortless five-lengths. And best of all, the Breeders' Cup was at Churchill Downs so he had already proven he could win on that track.

Fast forward to the first Saturday in May the next year. Arazi, with only one start since the Breeders' Cup, went to the gate as the odds-on favorite, according to John Eisenberg of the Baltimore Sun. He had none of the brilliance he had shown as a juvenile and wound up eighth. The remainder of his career would not be noteworthy.

2. Point Given, 2001

Eclipse Sportswire/Getty Images

Going into the 2001 Kentucky Derby (G1), nearly everyone believed Point Given was a lock. The imposing chestnut colt was drawing comparisons to the other "Big Red" with his stature and dominance, and he seemed practically unbeatable as they went to the starting gate.

But somehow, he was very beatable. He went off as the overwhelming favorite and spun his wheels, finishing fifth behind a very average winner in Monarchos. It would be his only loss from a total of seven starts as a three-year-old, and he went on to win both the Preakness Stakes (G1) and Belmont Stakes (G1) impressively.

Years later, in an interview with Lenny Shulman of Bloodhorse.com, Gary Stevens reflected on his loss in the Kentucky Derby and said, "Since 2001, he’s probably the best horse never to win the Triple Crown. You move on, but I’m still haunted by his loss in the Kentucky Derby."

1. Dancer's Image, 1968

Tasos Katopodis/Getty Images

Of all of the disappointments, none may have stung worse than Dancer's Image in 1968. A son of fellow Derby disappointment Native Dancer, Dancer's Image finished first in the 1968 Kentucky Derby. 

It was later discovered that he tested positive in a post-race urinalysis for phenylbutazone—a very common anti-inflammatory medication. There was significant controversy in the years that followed, and Peter Fuller staunchly believed he had been the victim of foul play, as he told the Associated Press (h/t Fox News). The drug is now legal, in restricted dosages, at many race tracks throughout the country.

Dancer's Image remains the only horse in the history of the Kentucky Derby to finish first but to have been disqualified.