The field for the 142nd Kentucky Derby will learn their starting gates at 5:30 p.m. Wednesday.

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If a Thoroughbred trainer is asked what their favorite race to win is, many will answer the Kentucky Derby. The Run for the Roses kicks off the Triple Crown excitement and a horse only gets one chance to run in the race. Below are the trainers who have not experienced the biggest victory at Churchill Downs once or twice, but three times or more. They are the trainers with the most Kentucky Derby wins.

Ben A. Jones (6): No other trainer has seen the success of Jones in the Kentucky Derby and no one has tied his record. The closest trainers have gotten is two wins less. Jones’ Kentucky Derby winners were Lawrin, (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), and Hill Gail (1952). Except for Lawrin, each horse was owned by Calumet Farm, with Whirlaway and Citation both being Triple Crown winners. Jones is one of two trainers to have won the Triple Crown twice.

Herbert J. Thompson (4): Switching from harness racing to Thoroughbred racing served Thompson well. His picked up horses for Colonel E.R. Bradley and won the Kentucky Derby with four horses, each owned by the Colonel. The four winners were Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932), and Brokers Tip (1933). Brokers Tip is one of the two maidens to win the Run for the Roses.

D. Wayne Lukas (4): Lukas is one of the best known names in racing. His first Kentucky Derby win came with the filly Winning Colors (1988), followed by Thunder Gulch (1995), Grindstone (1996), and Charismatic (1999). Thunder Gulch won the Kentucky Derby and Belmont while Charismatic won the Kentucky Derby and Preakness.

Bob Baffert (4): The fourth time was the charm for Baffert. He missed the Triple Crown with three different horses, but finally got the glory in 2015 with American Pharoah. Silver Charm (1997), Real Quiet (1998), and War Emblem (2002) all won the Kentucky Derby and Preakness, but missed the third jewel. This year Baffert could have Mor Spirit and Cupid in the Kentucky Derby. They sit at numbers 8 and 13 respectively on the Kentucky Derby leaderboard.

Jim Fitzsimmons (3): “Sunny Jim” Fitzsimmons is the only other trainer besides Ben A. Jones to win two Triple Crowns. His three Kentucky Derby wins came with Gallant Fox (1930), Omaha (1935), and Johnstown (1939), the first two being the horses that won the Triple Crown. Belair Stud was the owner of all three horses.

Max Hirsch (3): Hirsch’s first Kentucky Derby winner was Bold Venture (1936), who ended up siring two more Kentucky Derby winners for Hirsch. Bold Venture’s sons Assault (1946) and Middleground (1950) followed in their father’s footsteps, and Assault even won the Triple Crown.
 

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A horse writes their name in history when they win the Kentucky Derby. While the thrill of victory is always exciting, the horses below ran their hearts out at Churchill Downs to get to the top of the Kentucky Derby list and stamp their respective years into the 10 fastest editions of all time.


10.) Funny Cide, 2:01.19, 2003: Funny Cide, “the gutsy gelding,” was the first gelding since 1929 to win the Kentucky Derby. He was also the first New York bred to win the race. He went on to win the Preakness before finishing 3rd in the Belmont. Funny Cide now resides at the Kentucky Horse Park in the Hall of Champions.


9.) War Emblem, 2:01.13, 2002: War Emblem was one of three Bob Baffert trainees to win the Kentucky Derby and the Preakness, but fall short in the Belmont. He has returned to the U.S. after stud duties in Japan and is now retired at Old Friends in Georgetown, Kentucky.


8.) Fusaichi Pegasus, 2:01.12, 2000: Fusaichi Pegasus was the first favorite to win the Kentucky Derby since Spectacular Bid in 1979. He was 2nd in the Preakness and did not run in the Belmont. Ashford Stud is his current home where he stands as a stallion.


7.) Grindstone, 2:01.06, 1996: Grindstone was one of four horses trained by D. Wayne Lukas to win the Kentucky Derby and was sired by 1990 Kentucky Derby winner Unbridled. Unfortunately, Grindstone did not run again after his Kentucky Derby victory due to an injury.


6.) Proud Clarion, 2:00.60, 1967: Proud Clarion was a 30-1 upset in the Kentucky Derby. He followed that effort with a 3rd in the Preakness.


5.) Decidedly, 2:00.40, 1962: Decidedly was also sired by a previous Kentucky Derby winner. He was by Determine, who won the 1954 edition of the race.


4.) Spend a Buck, 2:00.20, 1985: Spend a Buck caused a Triple Crown uproar when his connections chose to skip the Preakness and Belmont and point their Kentucky Derby winner for the Jersey Derby, where he was eligible for a $2 million bonus. Luckily for his connections, Spend a Buck did win the Jersey Derby, but others were left feeling bitter with no shot of witnessing a Triple Crown that year.


3.) Northern Dancer, 2:00.00, 1964: Northern Dancer is one of the most prominent bloodlines in the Thoroughbred industry. He was a Canadian bred who won the Preakness following his Kentucky Derby win, but finished 3rd in the Belmont.


2.) Monarchos, 1:59.97, 2001: Some of the fastest fractions the Kentucky Derby has seen helped with this speedy victory. After winning the Kentucky Derby, Monarchos finished 6th in the Preakness and 3rd in the Belmont.


1.) Secretariat, 1:59.40, 1973: The immortal Secretariat holds not only has the fastest Kentucky Derby time, but the fastest Preakness and Belmont times as well. He was named champion three year old and horse of the year in 1973. Many still consider Secretariat to be the greatest racehorse ever.
 

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If you take a look at the Kentucky Derby times through the years, it is easy to see that the horses have gotten faster. The first Kentucky Derby was run in 1875 at Churchill Downs at a distance of 1 1/2 miles. In 1896, the distance was shortened to 1 1/4 miles. The times listed here are the 10 slowest editions of the race since the 1 1/4 miles distance was implemented. Even though most of the times have gotten faster over the years, the last few editions of the race may indicate that Kentucky Derby 2016 could be a bit slower.

1.) Stone Street, 1908, 2:15.20: Stone Street had not won any major stakes before his Kentucky Derby win, nor did he win any major stakes after. The 1908 Kentucky Derby was a muddy one, and as the other seven horses failed to perform their best, Stone Street excelled. He went off at odds of 24-1, and the minimum $5 bet cashed $123.60 to win.

2.) Pink Star, 1907, 2:12.60: Another sloppy track and another longshot. Pink Star ran on a Churchill track where the horses were in mud up to their fetlocks. He was retired the following year because of his bad temperament and lackluster races.

3.) Typhoon II, 1897, 2:12.50: Typhoon II was bred in Tennessee and beat the Derby favorite on a muddy track. His performance level fell after his three year old year and he eventually retired to a farm in Lexington as a pensioner. When his owner demanded the trainer to dispose of the horse because the paddock was needed for something else, the trainer gave him to a friend, who used him as a cart horse pulling hay for livestock.

4.) Manuel, 1899, 2:12.00: Manuel was bred in Louisville, Kentucky at Bashford Manor Stable. He missed the rest of his three-year-old year after stepping in a hole on Churchill Downs’ track. He faced only four other horses in the Derby.

5.) Exterminator, 1918, 2:10.80: Willis Sharpe Kilmer bought the gelding Exterminator to work alongside his two-year-old champion colt Sun Briar, who was to run in the Kentucky Derby. Kilmer often referred to Exterminator as "the goat," even though the gelding would run right with Sun Briar in workouts unless held back. To Kilmer's dismay, Sun Briar would not be Derby bound due to ringbone. Churchill Downs president Matt Winn had to convince Kilmer to run Exterminator. Off at 30-1 in the slop, Exterminator proved many people wrong and won by a length. He raced until the age of nine and ran 99 times, earning the nickname "Old Bones.” He lived out his retired life with companion ponies, each one named Peanut. Exterminator lived until he was 30.

6.) Clyde Van Dusen, 1929, 2:10.80: Clyde Van Dusen was the last gelding to win the Kentucky Derby before Funny Cide in 2003. He was a son of Man O'War, but was said to be "a mere pony of a horse with a weedy frame." Because of his appearance, he was named after his small statured trainer. The 1929 Kentucky Derby was run in the pouring rain and Clyde Van Dusen's mud caulks on his shoes helped him through the slop. He won by two lengths and beat the favorite and future horse of the year Blue Larkspur. Clyde Van Dusen was purchased by his trainer after his racing days to become an exercise pony.

7.) Agile, 1905, 2:10.75: Agile only faced two competitors when he won the Kentucky Derby. He also won the Phoenix Stakes in his three year old year, which used to be held at Lexington's Kentucky Association racetrack. Keeneland picked up the race in 1937 and it is still run today. Agile later became a family's carriage horse.

8.) Reigh Count, 1928, 2:10.40: Reigh Count certainly had a great run in both his race career and stud career. He won four races at two, including the Kentucky Jockey Club Stakes, and took the Kentucky Derby at three. He missed the Preakness and Belmont because of an injury, but came back later that year to beat the Preakness winner and receive Horse of the Year honors. He also won the Jockey Club Gold Cup that year against older horses. As a four year old, Reigh Count shipped to England and won the Coronation Cup before finishing second in the Ascot Gold Cup. He stood stud in Paris Kentucky and sired 22 graded stakes winners, including 1940 Triple Crown winner Count Fleet.

9.) Sir Barton, 1919, 2:09.80: With no win as a two-year-old, Sir Barton started his three-year-old year in the Kentucky Derby and was entered as a rabbit. Sir Barton flipped the tables and won the race, then took the Preakness and Belmont, becoming the first Triple Crown winner in America and 1919 Horse of the Year. At age four, Sir Barton took on Exterminator in the Saratoga Handicap and won. After a mostly unsuccessful stud career, Sir Barton served as a work horse for the U.S. Army Remount Service. He was then bought by a Wyoming rancher and lived out the rest of his days on his owner's ranch.

10.) Worth, 1912, 2:09.40: Not only did Worth win the Kentucky Derby, but he also became a U.S. champion racehorse in 1912. He was the top racehorse his two-year-old year based on earnings.
 

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Kentucky Derby Drink Prices.
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Nyquist and trainer Doug O'Neill at their barn earlier today. <figure class="feed-item-figure ">
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An undefeated favorite

Nyquist (7-for-7 lifetime) takes a perfect record into the Derby. Seven horses have won the Derby with an unblemished record. He is the first Breeders’ Cup Juvenile winner to enter the Derby with a perfect record.

Only four horses have entered the Derby undefeated and with more wins than Nyquist. Of the previous six to enter the Derby with at least seven wins, two won the race: Morvich in 1922 and Majestic Prince in 1969.

Nyquist will be the 27th horse to run in the Derby undefeated. He will also be the 16th undefeated horse to be favored in the Derby. Six of the 15 undefeated Derby favorites won. The worst finish by an undefeated Derby favorite is ninth by Private Terms in 1988.

Nyquist is the first Breeders’ Cup Juvenile winner to run in the Derby since 2012, when Hansen finished ninth. The only Breeders’ Cup Juvenile champion to win the Derby was Street Sense in 2007. (Note: The first Breeders’ Cup was held in 1984.)
 

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Favorites on a winning run.

Last year, American Pharoah made it three years in a row in which the favorite won the Derby, on his way to winning the Triple Crown and ending a 36-year drought. Before this stretch, the last time three successive favorites won the Derby was a run of four years from 1972 to 1975. Over the past 16 years, post-time favorites have won seven times, and five have won the last nine. From 1980 to 1999, favorites were 0-for-20.

Don’t discount a long shot to have a say in the outcome. Since 2000, there have been just as many winners with odds of 15-1 or worse, and the average price of the winner has been greater than during the period from 1980 to 1999. That tells you if the favorite doesn’t win, a real long shot could.

In four of the past five years, a horse that was at least 15-1 finished first or second, and in two of the past three years, a 30-1 shot ran second. Last year was the first time since 1996 that three horses with 10-1 odds or better completed the trifecta. The last time that happened in consecutive years was 1988-89.
 

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Notes on trainers

Bob Baffert can win his 13th Triple Crown race with a win in the Derby. That would tie him with Sunny Jim Fitzsimmons for second all time among trainers. Baffert will attempt to win consecutive Derbies for the second time. He is also the last trainer to win the Derby in consecutive years, with Silver Charm and Real Quiet in 1997 and 1998.

Steve Asmussen (Gun Runner, Creator) is winless with 13 Derby starters -- the most starters for a trainer without a win in the Derby. He has two in-the-money finishes: Curlin (third in 2007) and Nehro (second in 2011).

Todd Pletcher got his first Kentucky Derby win in 2010 with Super Saver. Of Pletcher’s 43 Derby starters, however, six have posted a top-three finish. His horses last year finished sixth, ninth and 10th. Pletcher will send Destin and Outwork to post Saturday.

Dallas Stewart has never won a Triple Crown race, but he has nearly pulled some stunners, running second four times at 28-1 or longer. Those horses represent the four longest-priced horses Stewart has run in a Triple Crown race. So there is reason to think Tom’s Ready could run a big race Saturday.
Asmussen, Pletcher and Chad Brown have multiple horses in this year’s field. A trainer has had two horses finish in the top three 12 times.

In the past 13 editions of the Derby, 11 have been won by a trainer who had previously never won the Derby. Baffert, Pletcher and Doug O’Neill are the only trainers in Saturday's race who have previously won it.
 

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Record within jockey Espinoza’s reach.

Victor Espinoza (Whitmore) can become the first jockey to win the Derby three years in a row. Six jockeys have won the Derby in consecutive years; Jimmy Winkfield in 1903 came the closest to winning the Derby in three straight years. He finished second aboard Early, three-quarters of a length behind winner Judge Hines.

Espinoza has three wins from seven Derby mounts. The first Hispanic jockey to win the Triple Crown, he has won five of the past six Triple Crown races and seven overall. His five Triple Crown wins over the past two years are the most by a jockey since Ron Turcotte in 1972 and 1973 on Riva Ridge and Secretariat.
 

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$30 win.....$30 place.....#5 Gun Runner

$1 Exacta Box.....5/20/14/15

$1 Exacta Box.....5/13/17/9

$1 Triple Box.....5/20/14/15

$1 Triple Box.....5/13/17/9
 

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