Kentucky Derby: Top 8 Horses Not To Win The Run For The Roses

Written By Darren Cooper on May 5, 2022
Best horses to never win Derby

The most well-known horse race in America goes off on Saturday with the 148th running of the Kentucky Derby. It’s drawn a 20-horse field.

All 20 horses carry unique stories and backgrounds. They also carry the hopes of their owners and trainers, and those who have put a few bucks down on them to win, place or show.

But there can only be one winner.

The Kentucky Derby, the first leg of the Triple Crown, is full of heartbreaking stories of champion horses who did not win at Churchill Downs.

Here are eight of the best horses who didn’t win the roses.

Bold Ruler (1957)

He’s the father of Big Red himself, Secretariat. Bold Ruler was the favorite to win the Kentucky Derby, but never got into his rhythm and finished fourth.

Bold Ruler would show his ability by winning the Preakness Stakes by two lengths. He was the overwhelming favorite at 17-20 in the Belmont Stakes but faded to third.

He was still the American Horse of the Year in 1957 and inducted into the National Museum of Racing and Hall of Fame in 1973.

Native Dancer (1953)

Imagine a horse that won 21 of his 22 races, but not the Kentucky Derby. That’s Native Dancer.

At Churchill Downs, Native Dancer was a 3-5 favorite. He had won the prestigious Horse of the Year award as a two-year-old, practically unheard of.

But he had trouble on his trip around the track, getting bumped twice and failing to get clear in time to track down the winner, Dark Star. Native Dancer would win the Preakness and was such a strong favorite at the Belmont that they didn’t allow show betting.

Dancer’s Image (1968)

The son of Native Dancer remains the subject of one of the most controversial Kentucky Derbies of all time. Dancer’s Image finished first at the Kentucky Derby in 1968 but was disqualified when traces of phenylbutazone, an anti-inflammatory drug, were found in his system.

There were all sorts of allegations made that the horse was given an extra dose by a rival. The drug was legalized in 1974, but the disqualification stood.

Alydar (1978)

Alydar won an unprecedented Triple Crown of sorts in 1978.

After winning the Florida Derby and Blue Grass Stakes, he was one of the favorites heading into the Kentucky Derby but finished second to Affirmed.

Alydar then finished second to Affirmed in the Preakness and the Belmont. Four of Alydar’s seven losses to Affirmed came by less than a length, and this rivalry is regarded as one of the best in horse racing history.

Risen Star (1988)

Eighteen horses have won both the Preakness and Belmont Stakes. Risen Star doesn’t get enough credit as maybe the best of the group.

The son of Secretariat waited too long to make his move against Winning Colors in the Kentucky Derby but roared past her to win the Preakness by two lengths.

In the Belmont, Risen Star won by an incredible 14 ¾ lengths. In doing so, he posted a time that still ranks as the fourth-fastest in the history of the race.

However, an injury in the Belmont prevented him from racing again. A Kentucky Derby prep race at Fair Grounds is named in his honor.

Point Given (2001)

People are always looking for the next Secretariat. The horse racing world thought it was Point Given in 2001.

He was a heavy favorite in the Kentucky Derby. However, he could only manage a fifth-place finish behind Monarchos, who won with the second-fastest time in Derby history.

Point Given rebounded to win the Preakness by two-and-a-half lengths two weeks later. He then added the Belmont, which he won by 12 lengths.

Point Given went on to win the Haskell Invitational and Travers Stakes that summer. He was retired after the Travers, but did enough to be named America’s Horse of the Year.

Empire Maker (2003)

Empire Maker prepped for the Kentucky Derby by winning the Florida Derby by almost 10 lengths. He then won the Wood Memorial after repelling a hard-trying New York-bred named Funny Cide.

In the Derby, though, Funny Cide turned the tables in an upset. He then added the Preakness two weeks later.

But Empire Maker, who skipped the Preakness, was ready for the Belmont. He cruised home over a very sloppy racetrack to deny Funny Cide a Triple Crown.

Curlin (2007)

Curlin is the first North American horse to win over $10 million in his career, but he did not win the roses.

The horse had not run as a two-year-old but was a 7-2 favorite to win the Kentucky Derby. He settled for third behind Street Sense.

Curlin got payback on Street Sense in the Preakness, but lost to filly Rags to Riches by a head in the Belmont.

He then blossomed into a globe-trotting superstar. The two-time Horse of the Year won the 2007 Breeders’ Cup Classic and added the Dubai World Cup the following spring.

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Darren Cooper

Darren Cooper was born and raised in Southern Louisiana, just a short pirogue ride away from New Orleans. He started his journalism career at the New Orleans Times-Picayune and has been a writer and columnist in New Jersey since 1998. He's won 14 statewide press awards and earned his first Associated Press Sports Editors Top 10 award in 2022.

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