Although everyone wants to make some money in the Kentucky Derby, betting the favorite will not
provide much of a return. The high payoffs come with the longshots. Since 1911,
it’s been tradition to place a $2 bet, and betting $2 on a longshot is a
minimum loss compared to what you could win. Below are the 10 horses with the
highest payoffs since the $2 bet came into play.
1.) Donerail (1913): No other horse
has come close to the longshot win that Donerail had in the Kentucky Derby. He
was sent off at odds of 91-1 and paid $184.90.
Donerail had a short career at stud in Lexington before being donated to
the Remount Service to produce horses for the cavalry.
2.) Mine That Bird (2009): Mine That Bird had four wins as a two-year-old in Canada and finished
second and fourth in New Mexico at age three. His trainer loaded the gelding in
a trailer attached to his pick-up truck and drove to Churchill Downs with a
broken foot. Mine That Bird was given 50-1 odds and paid $103.20 after his shocking win up the rail. He may not have won
another race after the Kentucky Derby, but his victory that day is not
3.) Giacomo (2005): Giacomo ties
with Mine That Bird for having the second highest Kentucky Derby odds at 50-1. He
looked promising after breaking his maiden by 10 lengths as a two-year-old, but
that was his only win going into the Kentucky Derby. His surprising win paid $102.60. Giacomo only won once more in
his racing career when he crossed the wire first by a head in the 2006 San
4.) Gallahadion (1940): Gallahadion was
owned by Ethel V. Mars’ Milky Way Farm. The farm’s name came from the chocolate
bar that Mars’ company produced. Gallahadion was another horse that did not see
as much success outside the Kentucky Derby. He was unplaced in two California
Derby preps, but the decision was made to enter him for the first Saturday in
May after he won the San Vicente and finished second in the Derby Trial. Off at
odds of 36-1, his win paid $72.40.
5.) Charismatic (1999): Before winning
the Kentucky Derby, Charismatic’s record held 3 wins out of 14 races. Those
victories came from a maiden claiming race, another claiming race, and the
Lexington Stakes. His 31-1 odds in the Kentucky Derby paid $64.60 to win.
6.) Proud Clarion (1967): Coming from a
top pedigree, Proud Clarion was given high expectations that he did not quite
live up to. He had no wins from three starts as a two-year-old, and only won a
few sprint races before the Kentucky Derby. His best prep for the race was the
Blue Grass where he finished second. He went off just over 30-1 in the Kentucky
Derby and paid $62.20. He had no
wins outside his three-year-old year.
7.) Exterminator (1918): When his owner’s
U.S. Champion Two-Year-Old Colt Sun Briar
scratched from the Kentucky Derby, Exterminator was grudgingly entered instead.
Having been bought merely as a work mate for Sun Briar, no one expected much
and Exterminator stunned the field at odds of 30-1 to pay $61.20. The gelding became known as “Old Bones” by his fans and
raced 99 times. He retired at age nine with a record of 50-17-17.
8.) Dark Star (1953): Even with odds
at 25-1, Dark Star won the Kentucky Derby and handed Native Dancer his only defeat. The upset paid $51.80. Dark Star won 6 of 13 races during his career.
9.) Thunder Gulch (1995): Though he had
won both the Fountain of Youth and the Florida Derby, Thunder Gulch was given
odds of 25-1 in the Kentucky Derby, where his win paid $51.00. He went on that year to win the Belmont, the Swap Stakes,
the Travers, and the Kentucky Cup Classic Handicap, earning Eclipse Champion
10.) Gato Del Sol (1982): With his only
two wins before the Kentucky Derby being at two-years-old, Gato Del Sol went
off at Churchill Downs
with odds of 21-1. His Kentucky Derby victory paid $44.40. He ran 39 times in his racing career, but only won four
other races after the Kentucky Derby.
By Christine Oser