Kentucky Derby Longshot Winners Led by Donerail

Mine That Bird Second Longest While Jockeys and Trainers Set Marks

© BarbaraAnne Helberg

May 5, 2009
In 135 runnings of the Kentucky Derby, Mine That Bird became the second largest longshot behind 1913's Donerail to win. His jockey and trainer also set historic marks.

For stretches of time in the history of the Kentucky Derby, betted favorites have been unable to win the classic. Such was the case for the year 2009, but over the last two seasons, the favorites, Big Brown in 2008 and Street Sense in 2007, were winners.

Big Payoffs From Kentucky Derby Longshots

Donerail, bred, owned, and trained by horseman T.P. Hayes of Kentucky, was an underdog in the 1913 Derby field of eight entrants. Yankee Notions was the pick of many Derby fans. Foundation and Ten Point also drew much of the betting.

Donerail defied the odds on May 10. Roscoe Goose had his first Derby mount, and he made the most of it, bringing Donerail home 1/2 length in front of Ten Point.

In just the third year of $2 mutuel betting, Donerail created a $2 bet payout of $184.90, a figure that still stands as the highest payoff ever in Derby history.

Mine That Bird's payoff was well behind Donerail's raw figure, but his payout of $103.20 per $2 bet is second highest all time.

Top Twelve Kentucky Derby Payoffs

  • No. 1 --- Donerail --- $184.90
  • No. 2 --- Mine That Bird --- $103.20
  • No. 3 --- Giacomo --- $102.60 in 2005
  • No. 4 --- Gallahadian --- $72.40 in 1940
  • No. 5 --- Charismatic --- $64.60 in 1999
  • No. 6 --- Proud Clarion --- $62.20 in 1967
  • No. 7 --- Exterminator --- $61.20 in 1918
  • No. 8 --- Dark Star --- $51.80 in 1953
  • No. 9 --- Thunder Gulch --- $51.00 in 1995
  • No.10 --- Gato Del Sol --- $44.40 in 1982
  • No.11 --- Bold Venture --- $43.00 in 1936
  • No.12 --- War Emblem --- $43.00 in 2002

Calvin Borel's Double Kentucky Oaks and Derby Win

Jockey Calvin Borel accomplished the first double win since 1993 on Kentucky Oaks day and Kentucky Derby day with Rachel Alexandra in the Oaks and Mine That Bird in the Derby.

Hall of Fame jockey Jerry Bailey doubled in 1993 with filly Dispute and Derby colt Sea Hero.

Kentucky Derby Trainers First Starting Entry Winners

In addition, the 2009 Derby yielded a win for trainer Bennie Woolley Jr., a first-time participant. In the last seven years, six conditioners entering their first Derby starter have won the race.

  • 2003 --- Funny Cide, trained by Barclay Tagg
  • 2004 --- Smarty Jones --- John Servis
  • 2005 --- Giacomo --- John Shirreffs
  • 2006 --- Barbaro --- Michael Matz
  • 2007 --- (Carl Nafzger won his second Derby with Street Sense)
  • 2008 --- Big Brown --- Richard Dutrow Jr.
  • 2009 --- Mine That Bird --- Bennie Woolley Jr.

Highest Payouts to Win 2003-1917

Since 1917, fourteen other Kentucky Derby winners have paid $20, or more on the purchase of a "to win" ticket.

  • 2003 --- Funny Cide --- $27.60
  • 2001 --- Monarchos --- $23.00
  • 1994 --- Go For Gin --- $20.20
  • 1993 --- Sea Hero --- $$27.80
  • 1992 --- Lil E. Tee --- $35.60
  • 1990 --- Unbridled --- $23.60
  • 1986 --- Ferdinand --- $37.40
  • 1980 --- Genuine Risk (f) --- $28.60
  • 1970 --- Dust Commander --- $32.60
  • 1951 --- Count Turf --- $31.20 ----- Royal Mustang --- $53.00
  • 1949 --- Ponder --- $34.00
  • 1923 --- Zev --- $40.00
  • 1920 --- Paul Jones --- $34.40
  • 1917 --- Omar Khayyam --- 27.60

In 1908, before the $2 mutual bet was instituted, Derby winner Stone Street paid out at $123.60 for a minimum $5.00 chance.


The copyright of the article Kentucky Derby Longshot Winners Led by Donerail in Thoroughbred Racing is owned by BarbaraAnne Helberg. Permission to republish Kentucky Derby Longshot Winners Led by Donerail in print or online must be granted by the author in writing.




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