Top 6 Best Kentucky Derby Races of All Time

Best Kentucky Derby Races of All Time

The Kentucky Derby is an annual horse racing competition held at Churchill Downs in Louisville, Kentucky. At this competition, three year old, Thoroughbred horses race along with their jockeys to compete for first place. A $3 million prize fund is split between the top five competitors. The first-place winner typically wins around $1.86 million, which is more than 60% of the total.


What are the best Kentucky Derby Races of all time?

  1. Secretariat, 1973
  2. Big Brown, 2008
  3. Mine That Bird, 2009
  4. Affirmed, 1978
  5. Monarchos, 2001
  6. Forward Pass, 1968

1. Secretariat, 1973

  • Secretariat was coached by jockey Ron Turcotte.
  • Ron Turcotte has 3,032 career wins.
  • Ron Turcotte’s career came to an abrupt stop in 1978 when his horse clipped heels with another horse, causing a catastrophic accident.

Turcotte began his racing career in 1960 as a hot walker (groomer) for E.P. Taylor's Windfields Farm in Toronto, but he quickly rose up the ranks and began winning races. Turcotte became recognized across the world in 1973 when he rode Secretariat to the first Triple Crown victory in 25 years. Secretariat, considered the greatest racehorse of all time, won the Kentucky Derby in 1973. Secretariat, nicknamed "Big Red'' because of his reddish-brown hue, set multiple records throughout his 16-month racing career. During this specific race of 1973, Secretariat’s rival Sham led the Kentucky Derby field of 14 horses until Secretariat caught up with him halfway down the finishing stretch. Secretariat ended up winning by two and a half lengths over Sham with a world-record finish time of 1:59 and 2/5ths. 

2. Big Brown, 2008

  • Big Brown was coached by the famous Jockey Kent Desormeaux
  • Kent Desormeaux has three Kentucky Derby victories to his credit (Big Brown, Fusaichi Pegasus, and Real Quiet).
  • Big Brown has won the Kentucky Derby, Florida Derby, Preakness Stakes, Haskell Invitational Handicap, and Monmouth Stakes.
  • Big Brown stands at 16.1 hands tall.
  • Big Brown won the Eclipse Award and the American champion 3-year-old male award in 2008.

During this memorable Kentucky Derby race in 2008, Kent Desormeaux rode Big Brown to victory. Kent Desormeaux is currently in the Jockey Hall of Fame and holds the U.S record for most races won in a single year, with 598 wins in 1989. Kent Desormeaux was raised in a remote farming community a few miles outside Maurice, Louisiana. He has had a deep connection to the countryside ever since his father purchased him his first saddle when he was a child. He has competed in thousands of races around the United States. However, his Kentucky Derby win of 2008 stands out the most. Big Brown raced alongside Eight Belles, resulting in Big Brown winning by four and three-quarter lengths. He began from the adverse outside post position No. 20, but neither that nor his lack of racing experience hampered him.

3. Mine That Bird, 2009

Mine That Bird
  • Chip Woolley trained Mine That Bird in 2009.
  • In 2005 and 2006, Wolley won a total of 9 races out of 183 he participated in, having a winning percentage of just 4.9%.
  • Mine That Bird was born in Kentucky and cost $9,500 to acquire.

Mine That Bird was trained by Chip Woolley in early 2009, and despite only finishing second and fourth in their two races together, Mine That Bird's qualified as the 19th horse out of 20 in the 2009 Kentucky Derby. Chip Woolley is somewhat known to be a “one-hit wonder” due to the single Kentucky Derby win he managed to pull off accompanied by Mine That Bird. During this particular race, Calvin Borel rode Mine That Bird, and right from takeoff, they were placed last out of 20 horses. As the race continued, Mine That Bird raced ahead of all its competitors and ended up winning first place. This surprised everyone because Mine That Bird was considered a huge underdog.

4. Affirmed, 1978

  • Affirmed was coached by jockey, Steven Cauthen
  • In 1977, Cauthen received the Eclipse Award for Outstanding Jockey and was named Associated Press Athlete of the Year.
  • In 1984, he received the George Woolf Memorial Jockey Award
  • Cauthen was the first jockey to win more than $6 million in a single year when working with agent Lenny Goodman in 1977.
  • Cauthen was the youngest jockey to win the U.S. Triple Crown in 1978. He was 18 years old at the time.
  • Affirmed was named 1978 Horse of the Year

Steven Cauthen was the son of a trainer and, as a result, grew up surrounded by horses in Walton, Kentucky. From the very beginning, Cauthen knew he wanted to pursue a career in horse racing because of his father’s influence and his small build. He began racing as soon as he could, and he came off as a natural from the start. Later in 1977, he led the country in race victories with 487. During this particular Kentucky Derby, Affirmed raced against a horse named Alydar, who was his number one rival at the time. Affirmed won by one and a half lengths over favored Alydar. With that being said, Affirmed managed to obtain this win by not exerting all his energy in the first lap around the track.

5. Monarchos, 2001

  • Monarcho was assisted by jockey Jorge Chavez.
  • Monarcho ran the second-fastest time in Kentucky Derby history.
  • Monarchos' timing of 1:59 4/5 was only two-fifths of a second slower than Secretariat's 1973 record mark.

Jorge Chaves began his racing career in Peru in 1982, where after five years, he quickly became Peru’s leading rider. He came to the United States in April 1988, where he competed with remarkable success at Florida race tracks. He moved to New York and soon became a leading rider in The New York Racing Association (NYRA). After multiple failed attempts, Jorge Chavez finally won the Kentucky Derby in 2001. Monarchos won the 127th Kentucky Derby by 4 3/4 lengths against Invisible Ink, ridden by John Velazquez. The second-place finisher, John Velazquez, complained that Jorge Chavez had interfered with him at the quarter-pole. The stewards wasted no time in rejecting the allegation. No winner of a Triple Crown race has ever been disqualified due to foul play on the track.

6. Forward Pass, 1968

  • Jockey Ismael Valenzuela trained Forward Pass.
  • Ismael Valenzuela is originally from Mexico, but at the age of 14, he moved to the United States and began working with quarter horses.
  • Valenzuela was inducted into the National Museum of Racing and Hall of Fame in 2008.

Ismael Valenzuela is also in the Jockey Hall of Fame, and he is more popularly known as Milo. Valenzuela has won a total of two Kentucky Derbys, once in 1960 and then again in 1968, riding the famous Forward Pass. During this particular race in 1968, Forward Pass won due to the disqualification of Dancer’s Image. Dancer’s Image raced accompanied by jockey Peter Fuller. Dancer’s Image was disqualified because officials completed a drug test, and it appeared that his veterinarian gave the horse a phenylbutazone tablet. The veterinarian did this in hopes of relieving inflammation of joints; this non-steroidal drug isn’t typically banned, although it’s considered illegal at the Kentucky Derby. Due to this mishap, Forward Pass stole the win right out from underneath Dancer’s Image.