Best horses to enter the Kentucky Derby undefeated and lose

Apr 20, 2023 Ashley Anderson/TwinSpires.com

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.

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.

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.

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.

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.