The best (and worst) moments that made the Kentucky Derby the holy grail of horse racing

This year’s Kentucky Derby on May 4 is not just any Kentucky Derby. It will mark the 150th running of the Run for the Roses.

To celebrate the milestone, Churchill Downs has renovated its paddock area, issued a 150th Kentucky Derby souvenir glass, a special 150th poster, a 150 limited edition bourbon whiskey by race sponsor Woodford Reserve, a limited edition anniversary watch by Longines and its first style guide in its history. That’s to name just a few mementos.

To mark this special occasion, we have assembled a “top three” in several categories regarding the history of America’s greatest race, dating back to Aristides’ win in the first Kentucky Derby in 1875 through Mage’s victory in 2023.

And we’re off!

Winningest trainers

▪ 6 — Ben Jones in 1938 (Lawrin), 1941 (Whirlaway), 1944 (Pensive), 1948 (Citation), 1949 (Ponder) and 1952 (Hill Gail).

▪ 6 — Bob Baffert in 1997 (Silver Charm), 1998 (Real Quiet), 2002 (War Emblem), 2015 (American Pharoah), 2018 (Justify) and 2020 (Authentic).

▪ 4 — Herbert J. Thompson in 1921 (Behave Yourself), 1926 (Bubbling Over), 1932 (Burgoo King) and 1933 (Brokers Tip).

▪ 4 — D. Wayne Lukas in 1988 (Winning Colors), 1995 (Thunder Gulch), 1996 (Grindstone) and 1999 (Charismatic).

After winning the 1938 Kentucky Derby with Lawrin for Woolford Farm of Prairie Village, Kansas, Benjamin A. Jones was hired by Warren Wright Sr. to be head trainer for Calumet Farm in Lexington. Jones won five runnings of the Kentucky Derby from 1941 through 1952 for Calumet. Included in those victories were a pair of Triple Crown winners in Whirlaway in 1947 and Citation in 1948.

Jones’ son Jimmy Jones won with Iron Liege in 1957 and Tim Tam in 1958 after his father had been appointed general manager by Calumet. Jones died in 1961 at age 78.

Bob Baffert has trained seven horses who finished first in the Kentucky Derby, but 2021 winner Medina Spirit was disqualified after testing positive for the presence of betamethasone, which is banned on race days in Kentucky. The 71-year-old Baffert has been suspended by Churchill Downs since 2021.

Winningest active trainers

▪ 6 — Bob Baffert in 1997 (Silver Charm), 1998 (Real Quiet), 2002 (War Emblem), 2015 (American Pharoah), 2018 (Justify) and 2020 (Authentic).

▪ 4 — D. Wayne Lukas in 1988 (Winning Colors), 1995 (Thunder Gulch), 1996 (Grindstone) and 1999 (Charismatic).

▪ 2 — Nick Zito in 1991 (Strike the Gold) and 1994 (Go for Gin).

▪ 2 — Doug O’Neill in 2012 (I’ll Have Another) and 2016 (Nyquist).

▪ 2 — Todd Pletcher in 2010 (Super Saver) and 2017 (Always Dreaming).

Pletcher and Lukas both have Kentucky Derby 150 candidates. Pletcher trains 2023 Breeders’ Cup Juvenile and Florida Derby winner Fierceness. Lukas trains Arkansas Derby runner-up Just Steel.

Oldest trainers to win

▪ At age 77, Art Sherman won the 2014 Kentucky Derby with California Chrome.

▪ At age 76, Charlie Whittingham won the 1989 Kentucky Derby with Sunday Silence.

▪ At age 71, MacKenzie Miller won the 1993 Kentucky Derby with Sea Hero.

Art Sherman was the exercise rider for 1955 Kentucky Derby winner Swaps before becoming a licensed jockey in 1957. He switched to training in 1979 and had won just 15 graded stakes races when California Chrome burst on the scene in 2014. Chrome won the Grade 2 San Felipe and Grade 1 Santa Anita Derby before winning the Grade 1 Kentucky Derby and Grade 1 Preakness.

A Hall of Famer, Charlie Wittingham won two runnings of the Kentucky Derby while in his 70s. At age 73, he won the 1986 Derby with Ferdinand. Three years later, he won with Sunday Silence, who went on to win the Preakness before finishing second to Easy Goer in the Belmont.

Youngest trainers to win

▪ At age 24, James Rowe Sr. won the 1881 Kentucky Derby with Hindoo.

▪ At age 27, Hollie Hughes won the 1916 Kentucky Derby with George Smith.

▪ At age 31, Don Combs won the 1970 Kentucky Derby with Dust Commander.

Though records are incomplete, James Gordon Rowe Sr. is believed to be the youngest trainer to win the Kentucky Derby. The Richmond, Virginia, native was 24 when he trained Hindoo to the 1881 Derby win. Rowe started out as a jockey before weight forced him to switch to training at the age of 18. He died at Saratoga, New York, at the age of 71.

Winningest owners

▪ 8 — Calumet Farm in 1941 (Whirlaway), 1944 (Pensive), 1948 (Citation), 1949 (Ponder), 1952 (Hill Gail), 1957 (Iron Liege), 1958 (Tim Tam) and 1968 (Forward Pass).

▪ 4 — Edward R. Bradley in 1921 (Behave Yourself), 1926 (Bubbling Over), 1932 (Burgoo King) and 1933 (Brokers Tip).

▪ 3 — Belair Stud in 1930 (Gallant Fox), 1935 (Omaha) and 1939 (Johnstown).

The legendary Calumet Farm dominated thoroughbred racing under founding owner William Monroe Wright (1924-32) and his son Warren Wright Sr. (1932-50) and Warren’s daughter, Lucille Parker Wright Markey (1950-82). The farm is now owned by Brad M. Kelley.

A self-described speculator, Edward R. Bradley was the leading owner and breeder of thoroughbred racehorses from 1889 through 1933. He purchased what he named Idle Hour Stock Farm near Lexington in 1906. Trainer Herbert “Derby Dick” Thompson’s four Kentucky Derby wins were all with horses owned by Bradley.

William Woodward Sr. owned Belair Stud, which produced three Kentucky Derby winners for trainer Jim “Sunny Jim” Fitzsimmons. Woodward partnered with A.B. Hancock Sr. to purchase English sire Sir Gallahad III and bring him to the United States. Sir Gallahad III was sire to 1930 Kentucky Derby winner Gallant Fox.

Winningest jockeys

▪ 5 — Eddie Arcaro in 1938 (Lawrin), 1941 (Whirlaway), 1945 (Hoop Jr.), 1948 (Citation) and 1952 (Hill Gail).

▪ 5 — Bill Hartack in 1957 (Iron Liege), 1960 (Venetian Way), 1962 (Decidedly), 1964 (Northern Dancer) and 1969 (Majestic Prince).

▪ 4 — Bill Shoemaker in 1955 (Swaps), 1959 (Tomy Lee), 1965 (Lucky Debonair) and 1986 (Ferdinand).

Born in Cincinnati, Eddie Arcaro earned five Kentucky Derby victories from 1938 through 1952. He holds the record for most wins in both the Preakness and Belmont Stakes with six each. He won the Triple Crown aboard both Whirlaway and Citation. Arcaro died in 1997 at age 81.

Born in Pennsylvania, Hartack earned five Kentucky Derby wins from 1957 through 1969. He won over 4,000 races n the U.S. before moving to Hong Kong in 1974. He died in 2007 at the age of 74.

Winningest active jockeys

▪ 3 — Kent Desormeaux in 1998 (Real Quiet), 2000 (Fusaichi Pegasus) and 2008 (Big Brown).

▪ 3 — Calvin Borel in 2007 (Street Sense), 2009 (Mine That Bird) and 2010 (Super Saver).

▪ 3 — Victor Espinoza in 2002 (War Emblem), 2014 (California Chrome), 2015 (American Pharoah).

▪ 3 — John Velazquez in 2011 (Animal Kingdom), 2017 (Always Dreaming) and 2020 (Authentic).

Oldest winning jockeys

▪ At age 54, Bill Shoemaker won the 1986 Kentucky Derby on Ferdinand.

▪ At age 52, Mike Smith won the 2018 Kentucky Derby on Justify.

▪ At age 49, John Velazquez won the 2020 Kentucky Derby on Authentic.

The legendary Bill Shoemaker won his first Kentucky Derby in 1955 at age 23 aboard Swaps for owner Rex Ellsworth. He won his fourth Kentucky Derby in 1986 at age 54 aboard Ferdinand for 73-year-old trainer Charlie Whittingham.

Youngest winning jockeys

▪ At age 15, Alonzo “Lonnie” Clayton won the 1892 Kentucky Derby on Azra.

▪ At age 15, James “Soup” Perkins won the 1895 Kentucky Derby on Halma.

▪ At age 16, Bill Boland won the 1950 Kentucky Derby on Middleground.

Alonzo “Lonnie” Clayton was an exercise rider at age 12 in New Jersey and won the Travers at age 14 and then the Kentucky Derby. Perkins began riding at age 11 for his father, who was a trainer.

Coldest Derby days

▪ 47 degrees on May 4, 1957.

▪ 47 degrees on May 4, 1935.

▪ 57 degrees on May 10, 1919.

According to the National Weather Service, the record for the lowest high temperature on Kentucky Derby day is a tie at 47 degrees on both 1935 and 1957. Omaha won the race in 1935. Iron Liege was the 1957 winner.

Hottest Derby days

▪ 94 degrees on May 2, 1959.

▪ 90 degrees on May 9, 1889.

▪ 90 degrees on May 20, 1879.

According to the National Weather Service, Tomy Lee was the winner on he hottest Kentucky Derby day, a scorching 94 degrees in 1959.

Wettest Kentucky Derby days

▪ 3.15 inches on May 5, 2018.

▪ 2.31 inches on May 11, 1918.

▪ 1.46 inches on May 5, 2012.

On May 5, 2018, Justify won the wettest Kentucky Derby when the National Weather Service measured 3.15 inches of rain n Louisville.

Most controversial Kentucky Derbys

▪ 1968 — Dancer’s Image disqualified.

▪ 2019 — Country House declared winner after Maximum Security was disqualified.

▪ 2021 — Medina Spirit disqualified.

The Dancer’s Image disqualification after a drug test in 1968 qualifies as the most controversial Kentucky Derby. The race result was tied up in courts for years until Forward Pass was finally declared the winner.

Country House was the first Kentucky Derby winner via an on-track disqualification when Maximum Security was taken down for interference.

Largest Derby field

▪ 23 — 1974 Kentucky Derby.

Trained by Woody Stephens, Cannonade won the 1974 Kentucky Derby, which was the 100th running of the race. A crowd of 163,628 packed Churchill Downs that day. In 1975, Churchill Downs announced it was limiting the number of Kentucky Derby entries to 20 horses.

Smallest Derby field

▪ 3 — 1892 Kentucky Derby.

▪ 3 — 1905 Kentucky Derby.

Just three horses entered both the 1892 and 1905 runnings of the Kentucky Derby. Azra beat two other competitors in 1892. Agile did the same in 1905.

Largest Derby Day crowds

▪ 170,500 saw the 2015 Kentucky Derby won by American Pharoah.

▪ 167,227 saw the 2016 Kentucky Derby won by Nyquist.

▪ 165,307 saw the 2012 Kentucky Derby won by I’ll Have Another.

Kentucky Derby attendance has dipped the past few years with 147,294 for Rich Strike’s 2022 win and 150,335 for Mage’s 2023 victory.

The three fillies who have won

▪ 1988 — Winning Colors.

▪ 1980 — Genuine Risk.

▪ 1915 — Regret.

Trained by LeRoy Jolley, Genuine Risk became the first filly to win the Kentucky Derby in 65 years and just the second in history.

Last three geldings to win

▪ 2009 — Mine That Bird.

▪ 2003 — Funny Cide.

▪ 1929 — Clyde van Dusen.

A total of nine geldings have won the Kentucky Derby. They are Vagrant (1876), Apollo (1882), Macbeth II (1888), Old Rosebud (1914), Exterminator (1918), Paul Jones (1920), Clyde Van Dusen (1929), Funny Cide (2003) and Mine That Bird (2009).

Fastest Derby-winning times

▪ 1:59.40 — Secretariat in 1973.

▪ 1:59.97 — Monarchos in 2001.

▪ 2:00.20 — Spend a Buck in 1985.

The legendary Secretariat owns the track record for all three Triple Crown races — the Kentucky Derby, the Preakness and the Belmont Stakes in 1973.

Slowest Derby-winning times

▪ 2:15.20 — Stone Street in 1908.

▪ 2:12.60 — Pink Star in 1907.

▪ 2:12.50 — Typhoon II in 1897.

Listed are the times for the race run at 1 1/4 miles. The Kentucky Derby was originally 1 1/2 miles before being changed to 1 1/4 miles in 1896. The slowest winning Kentucky Derby time in the last 50 years is 2:05.00 by Sunday Silence in 1989.

The most tragic Kentucky Derby

▪ 2008 — Eight Belles dies after finishing second.

The filly Eight Belles broke down just past the wire after finishing second in the 2008 Kentucky Derby for owner Rick Porter and trainer Larry Jones. Having suffered compound fractures of both front ankles, she was euthanized on the track. Since 2009, the Eight Belles Stakes has been run on Kentucky Derby day in her honor.

Largest margins of victory by lengths

▪ 8 — Old Rosebud in 1914.

▪ 8 — Johnstown in 1939.

▪ 8 — Whirlaway in 1941.

▪ 8 — Assault in 1946.

Since 1947, Barbaro in 2006 and Mine That Bird in 2009 are tied for the largest winning margin in the Kentucky Derby. Each horse won the race by 6 1/2 lengths.

Largest odds for winners

▪ 91-1 — Donerail in 1913.

▪ 80-1 — Rich Strike in 2022.

▪ 65-1 — Country House in 2019.

Bred and owned by Thomas P. Hayes near Lexington, Donerail was the surprise winner of the 1913 Kentucky Derby at 91-1. It was the first Kentucky Derby in which the minimum bet was reduced to $2.

Largest $2 winning payouts

▪ $184.90 for Donerail in 1913.

▪ $163.60 for Rich Strike in 2022.

▪ $132.40 for County House in 2019.

After Donerail, Rich Strike was the longest shot at 80-1 to win the Kentucky Derby. Trained by Eric Reed, Rich Strike had only a maiden win before capturing the 2022 Kentucky Derby.

Largest $2 Derby exacta payouts

▪ $9,814.80 in 2005 for Giacomo and Closing Argument.

▪ $4,101.20 in 2022 for Rich Strike and Epicenter.

▪ $3,009.60 in 2019 for Country House and Code of Honor.

Since 1985 the exacta (first- and second-place finishers) has paid at least $1,000 six times — the listed three plus $2,074.80 in 2009 with Mine That Bird and Pioneerof the Nile; $1,300.80 in 2002 with War Emblem and Proud Citizen; 1,229.00 in 2001 with Monarchos and Invisible Ink.

Largest Derby $1 superfecta payouts

▪ $864,253.50 in 2005 for Giacomo, Closing Argument, Afleet Alex and Don’t Get Mad.

▪ $557,006.40 in 2009 for Mine That Bird, Pioneerof the Nile, Musket Man and Papa Clem.

▪ $321,500.10 in 2022 for Rich Strike, Epicenter, Zandon and Simplification.

The 2005 Kentucky Derby featured a huge superfecta (first-, second-, third- and fourth-place finishers) payout thanks to long shots hitting the board. Giacomo won at 50-1, followed by runner-up Closing Argument at 72-1, third-place finisher Afleet Alex at 9-2 and fourth-place finisher Don’t Get Mad at 29-1. Favorite Bellamy Road (5-2) finished seventh.