Best horses to enter the Kentucky Derby undefeated and lose

Apr 20, 2023 Ashley Anderson/TwinSpires.com

Essential Quality (Photo by Coady Media/Oaklawn Park)

Originally published April 30, 2023

Dating back to the 1915 Kentucky Derby (G1), 34 horses have entered the event with an undefeated record, with 18 of those sent off as the post-time favorite in the race.

Nine of the unbeaten Derby starters prevailed in the Run for the Roses, including Triple Crown winners Justify (2018) and Seattle Slew (1977), as well as Nyquist (2016), Big Brown (2008), Barbaro (2006), Smarty Jones (2004), Majestic Prince (1969), Morvich (1922), and the filly Regret (1915).

Maximum Security was also 4-for-4 lifetime heading into the Kentucky Derby and crossed the finish line first, but he was disqualified to 17th for interference.

Below we explore those horses who came up short in the most exciting two minutes in sports while suffering their first lifetime defeat. From Champion Two-Year-Olds to Breeders’ Cup Classic (G1) heroes and eventual prominent sires who bore talented offspring, here are the best horses to enter the Kentucky Derby undefeated and lose.

1. Essential Quality, 2021

Just the 14th colt to earn both Champion Two-Year-Old and Champion Three-Year-Old honors, Essential Quality lived up to the hype as a juvenile, as the Tapit colt went 3-for-3, capping his two-year-old season with a victory in the 2020 Breeders’ Cup Juvenile (G1).

The Brad Cox pupil then launched his sophomore campaign with a 4 1/4-length win in the Southwest S. (G3), before he beat Highly Motivated by a neck to conquer the Blue Grass S. (G2) at Keeneland.

The Godolphin-bred looked primed for a Kentucky Derby victory and went off as the 2.90-1 favorite in the 2021 Run for the Roses. However, 12-1 shot Medina Spirit broke sharply to go gate-to-wire in a time of 2:01.02. The Bob Baffert trainee was later disqualified after testing positive for a banned substance, and Essential Quality’s stablemate Mandaloun, a 26.90-1 longshot, was elevated to first. Essential Quality crossed the wire fourth following a troubled trip.

He rebounded from his first career loss with a win in the Belmont (G1), then triumphed in the Jim Dandy S. (G2) and Travers (G1). Essential Quality closed out his career with a third to stablemate Knicks Go in the 2021 Breeders’ Cup Classic (G1) before he retired to stand at stud at Darley’s Jonabell Farm in 2022.

2. Curlin, 2007

With just three races under his belt before his Kentucky Derby start, Curlin was named the 7-2 morning line favorite by Mike Battaglia, but history was not on the side of the Smart Strike colt.

At the time, no horse had won the Derby with just three previous starts since Regret in 1915, and no runner had triumphed in the Derby without racing as a two-year-old since 1882.

Perhaps Curlin’s inexperience led the betting public to back the Carl Nafzger-trained Street Sense, who had won the Tampa Bay Derby (G3) and finished a nose in second in the Blue Grass earlier in the year. The Street Cry son went off as the slight 4.90-1 favorite and ultimately crossed the finish line first, with 5-1 second choice Curlin coming home eight lengths behind in third.

Curlin’s setback was short-lived, though. He rebounded to beat Street Sense by a head in the Preakness (G1), but the Steve Asmussen runner was then upset by a head by the filly Rags to Riches in the Belmont.

Curlin would conclude his three-year-old season with a third in the Haskell (G1) and victories in the Jockey Club Gold Cup (G1) and Breeders’ Cup Classic to secure the Eclipse Award for Champion Three-Year-Old.

As a four-year-old, Curlin’s only losses were off the dirt: second in the Man o’ War S. (G1) on turf, and fourth in his return to the Breeders’ Cup Classic, on the all-weather track Santa Anita was then using.

The Champion Older Male Horse of 2008, Curlin retired to stud soon after as the highest North American money earner at the time, with more than $10.5 million obtained from a 16-11-2-2 record. Among his notable offspring are Belmont champion Palace Malice, Preakness winner Exaggerator, Travers hero Keen Ice, and Champion Three-Year-Old Filly recipients Nest and Malathaat, who also won Champion Older Dirt Female Horse in 2022.

3. Native Dancer, 1953

Out of 22 career starts, Native Dancer failed to win just one — the 1953 Kentucky Derby.

Prior to the first leg of the Triple Crown, the gray son of Polynesian had won nine straight races as a juvenile, including the Saratoga Special and Hopeful Stakes, to collect Horse of the Year honors. As a sophomore, he succeeded in the Gotham and Wood Memorial, which led to Native Dancer garnering a bevy of attention from the public, both in the press and at the betting windows.

As the 3-5 post-time favorite of the Derby, the Bill Winfrey pupil encountered traffic trouble and raced wide before attempting to rally late, coming up short to place a head second to 25-1 longshot Dark Star.

Native Dancer made his next start in the Withers at Belmont Park on May 16 and would never lose again from there, scoring victories in the Preakness and Belmont along the way.

He retired due to injury at age four but was still voted American Horse of the Year in 1954, as well as in the years of 1952 and 1953. A major sire and influential broodmare sire, Native Dancer’s offspring include 1966 Kentucky Derby winner Kauai King.

4. Bimelech, 1940

Unbeaten in eight races ahead of his Derby start, Bimelech was a 2-5 choice in the race, the lowest odds quoted for a Derby favorite at the time. The Champion Two-Year-Old had already won the Saratoga Special, Hopeful, and Blue Grass, as well as the Derby Trial S., where he beat Gallahadion.

That same rival would repay Bimelech with a surprise victory in the 1940 Run for the Roses as a 35-1 longshot. The race would mark Bimelech’s third start in eight days, but jockey Fred Smith blamed himself for the loss, as Bimelech drifted wide the entire trip and tired in the final furlongs as Gallahadion passed him.

Bimelech returned to race in the Preakness, where he beat Gallahadion, then placed second in the Withers. With inadequate preparation reportedly the culprit for his defeat in New York, the bay son of Black Toney went into heavy training before visiting the winner’s circle in the Belmont S.
Following his next race, an injury was discovered in his foot and he was benched for the remainder of the year. Bimelech managed to win Champion Three-Year-Old in 1940 and retired to stud as a four-year-old with a 15-11-2-1 record.