Methodology: Each horse’s rating is based on the standard deviation of the distance covered as of the time the winner crossed the finish line measured against the average of other race finishers unless unless a horse finished more than one-half standard deviation behind the horse immediately ahead of it. If the latter occurs, that horse’s distance and the distances of all subsequent horses are not considered. The Kentucky Derby is a 1.25 mile race, a distance that translates to 6,600 feet. In racing, distances behind the leader are measured in lengths, a measure commonly standardized at eight feet per length. Therefore, a horse finishing one length behind the winner is presumed to have covered 6,592 feet as of the time the winner crossed the finish line. The following example, from the 2015 Kentucky Derby won by Triple Crown winner American Pharoah illustrates the method. Eighteen horses started the race of which 12 finished close enough behind the leader to qualify for inclusion in the rating. The field average distance covered by those 12 was 6,544 feet; the standard deviation was 33.42 feet:
Place Horse/Jockey Lengths Distance St. Dev.
- American Pharoah/Espinoza 6,600 67
- Firing Line/Stevens 00 6,592 1.43
- Dortmund/Garcia 00 6,576 0.95
- Frosted/Rosario neck 6,574 89
- Danzig Moon/Leparoux 25 6,548 0.12
- Materiality/Castellano 25 6,538 -0.19
- Keen Ice/Desmoreaux 00 6,530 -0.42
- Mubtaahij/Soumillon 75 6,524 -0.60
- Itsaknockout/Saez 75 6,518 -0.78
- Carpe Diem/Velazquez 75 6,518 -0.78
- Frammento/Nakatani 00 6,510 -1.02
- Bolo/Bejarano 75 6,502 -1.26
- Z/Vazquez 2.75
- Ocho Ocho Ocho/Trujillo head
- Far Right/Smith head
- War Story/Talamo 50
- Tencendur/Franco 75
- Upstart/Ortiz 50
Summary: To dedicated race fans, the most surprising element of the following list will be the absence of more than half of the Triple Crown winners in history…among them American Pharoah, who has noted above rated 1.67. These absences are due to a variety of factors. For the record, here are the standard deviations of the performances of the other six Triple Crown winners not among the all-time top 25 Kentucky derby winners: Seattle Slew (1977) 1.67, Gallant Fox (1930) 1.66, Omaha (1935) 1.55, Sir Barton (1919) 1.52, Citation (1948) 1.27, Affirmed (1978) 1.26. An additional word about Citation, the 1948 Triple Crown winner often numbered among the greatest thoroughbreds in racing history. It is no criticism of Citation’s overall achievements to say that his Kentucky Derby performance, while victorious, was not particularly exceptional. He won by 3.5 lengths over a weak field of just six. Beyond that, the runner-up, Coaltown, was Citation’s stablemate, and Coaltown ran as a pacesetter for Citation, who passed Coaltown in the stretch and pulled away.
Disclaimer: Our perceptions of the strength of individuals (or teams) can be colored by factors that are extraneous to their actual dominance: general familiarity, the presence or absence of attention-getting personalities, national affinities, subjective opinions that become engrained over time, superiority in certain statistical categories being the most likely. This rating is based on an objective methodology, meaning that it is immune to influence from any of those criteria. That also means its findings may vary – in some cases substantially – from the historical consensus. As you scan this list, be prepared to have your presumptions of relative greatness challenged.
Each paragraph is headed by the name of the horse, year, jockey, odds and standard deviation score.
25: Determine, 1954, Raymond York, 4.3-to-1, 1.78. Going off as part of an entry pegged as the second favorite, Determine survived a jostled start to overtake Hasty Road at the head of the stretch and win going away.
24: Count Fleet, 1943, Johnny Longden, 0.4-to-1, 1.79. The overwhelming favorite based on his four victories as a two-year-old, Count Fleet assumed the lead at the outset and was never headed. Jockey Johnny Longden, who would ride County Fleet to that season’s Triple Crown, kept him well in front of eventual runner-up Blue Swords, finishing three lengths to the good.
23: California Chrome, 2014, Victor Espinoza, 2.5-to-1, 1.813. Rated close to the lead from early in the race, California Chrome moved in front around the final turn and his driving finish wore down Samraat, who faded from a challenging position to finish fifth. California Chrome beat longshot Commanding Curve by nearly two lengths. Chrome went on to win the Preakness before managing only a fourth place finish in the Belmont.
22: Thunder Gulch, 1995, Gary Stevens, 24-5-to-1, 1.822. Held just off the lead in a tightly packed field through the first mile, Thunder Gulch passed Serena’s Song at the head of the stretch and won a battle with Tejano Run for the finish line by nearly four lengths.
21: Barbaro, 2006, Edgar Prado, 6.1-to-1, 1.860. Race fans are familiar with the tragic story of Barbaro, who left the Derby as a Triple Crown favorite only to break down in the Preakness and eventually be euthanized. Only the second betting favorite when the Derby began, Barbaro stumbled at the start but caught the leaders at the far turn and reached the lead by the sixteenth pole. From there he won inspirationally, opening up a six and one-half length advantage by the finish line.
20: Proud Clarion, 1967, Ron Ussery, 30-to-1., 1.861. A 30-to-1 shot at the race’s start, Proud Clarion broke inauspiciously behind the heavy favorite, Damascus, and ran eighth at the halfway point. Forced outside as Ron Ussery positioned him for stretch run, he circled the field and caught leader Barb’s Delight and ran him down in the final furlong, winning by a length.
19: Monarchos, 2001, Jorge Chavez, 10.5-to-1, 1.873. Bumped at the start, Monarchos was pulled back at the race’s outset, standing only 10th at the three-quarter mile mark. But a strong sustained rush pulled him up to sixth at the mile mark and to second at the head of the stretch. From there he pulled away from Congaree to win by more than four lengths.
18: Pompoon, 1937, Harry Richards, 8-to-1, 1.874. Pompoon is the only horse among the 25 most dominant who did not actually win the race. He had a good excuse, running against War Admiral, a future Triple Crown winner and one of racing’s all-time great horses. This should not diminish Pompoon’s own run. Close to the pace all the way, he worked his way to second place – a length and a half behind War Admiral – by the mile mark. Although unable to catch the eventual winner, he did rout the rest of the 20-horse field, finishing eight lengths ahead of the third place finisher.
17: Unbridled, 1990, Craig Perret, 10.8-to-1, 1.927. Only the fifth betting favorite, Unbridled broke badly in a tightly packed 15-horse field and was 12th a half mile into the race. But jockey Craig Perret found running room outside entering the stretch, enabling him to tap Unbridled’s speed heading home. He won by three and one-half lengths.
16: Count Turf, 1951, Conn McCreary, 14.6-to-1, 1.931. Despite being the son of 1943 Derby winner Count Fleet and grandson of 1928 winner Reigh Count, Count Turf was so lightly regarded that he was part of a five-horse field entry. Count Turf came from fourth at the mile marker and won going away, his final margin put at four lengths.
15: Street Sense, 2007, Calvin Borel, 4.9-to-1, 1.932. The first of Calvin Borel’s three Kentucky Derby champions, Street Sense ran a conservative race that saw him 17th in a 20-horse field at the three-quarters mile mark. Running in Borel’s favorite position on the rail, Street Sense found enough running room deep on the backstretch to move all the way to third by the mile mark. He took the lead from Hard Spun at the head of the stretch and won by nearly four lengths.
- Gato Del Sol, 1982, Eddie Delahoussaye, 21-to-1, 1.95. Jockey Eddie Delahussaye broke Gato Del Sol easily, positioning him at the back of a 19-horse field as late as the half mile mark. Finding ample running room on the outside, Gato Del Sol advanced easily up the backstretch, working his way to fifth by the mile mark. As the leaders faded, Gato Del Sol displayed plenty in reserve for a stretch run that saw him hold off a fast-closing Laser Light for a two and one-half length victory.
13: Always Dreaming, 2017, John Velazquez, 5-to-1, 1.96. The weak betting favorite in a 19-horse field, Always Dreaming stalked longshot State of Honor down the backstretch, gradually drew away and fought off other challengers into the home stretch. He won by two and three-quarters lengths.
12: Hill Gail, 1952, Eddie Arcaro, 1.10-to-1, 2.00. With Eddie Arcaro in the saddle, Hill Gail went off as almost an even money favorite in the field of 16, took the lead at the outset, withstood a brief challenge from Hannibal on the backstretch, then opened up a five-length lead by the mile marker. Perhaps eased a bit toward the finish, he won by two lengths.
11: Smarty Jones, 2004, Stewart Elliott, 4-to-1, 2.02. The betting favorite, Smarty Jones stalked the early leader, Lion Heart, down the backstretch, challenged him three-quarters of a mile from the finish, seized the lead with a furlong remaining and pulled away to a three-length win. He would go on to win the Preakness and then see his Triple Crown hopes dashed by a runner-up finish at the Belmont Stakes.
10: Big Brown, 2008, Kent Desormeaux, 2.4-to-1, 2.03. The heavy favorite due to a series of sensational winter and spring performances, Big Brown worked his way forward from the 20th starting position to seize the lead with a quarter mile to go. The rest was easy, Desormeaux gradually building a five-length winning margin. Like Smarty Jones, Big Brown added the Preakness and went to the Belmont Stakes a heavy favorite to complete the Triple Crown, only to finish that race well out of the money.
- Reigh Count, 1928, Chick Lang, 2.06-to-1, 2.08. A dominant two-year-old, Reigh Count demonstrated why he was the clear betting favorite. Close to the front virtually from the start, he forced the leader, Misstep until overtaking him down the stretch and winning by three lengths. Reigh Count was the sire of Derby winner County Fleet and the grandfather of Derby winner Count Turf.
- Twenty Grand, 1931, Charles Kurtsinger, 0.88-to-1, 2.09. Possibly the shortest favorite in Derby history, Twenty Grand broke leisurely but gained momentum entering the backstretch and began relentlessly wearing down the rest of the 12-horse field. He won by four lengths. Jockey Charles Kurtsinger would also ride Twenty Grand to a Belmont victory, and would add the Preakness in 1933. In 1937, aboard War Admiral, Kurtsinger won the Triple Crown.
7: Hoop Jr., 1945, Eddie Arcaro, 3.7-to-1, 2.11. Hoop Jr. is often overlooked today, having run in an era that also produced such racing legends as Triple Crown winners Count Fleet, Assault and Citation. Still he went to the Derby post as the second favorite in the final race of the World War II era, seized the lead early and was never headed. Arcaro’s horse opened up a six-length lead by the head of the stretch and gave none of it back.
- Pensive, 1944, Conn McCreary, 7-to-1, 2.12. The 16-horse race quickly broke down into a battle between Pensive, Broadcloth and the heavy favorite, Stir Up. At the top of the stretch, Broadcloth and Stir Up staged a neck-and-neck battle, but that effort exhausted both, and Pensive overtook them in the final furlong to win by four. Pensive nearly completed the Triple Crown, adding the Preakness and finishing a close second in the Belmont. Jockey Conn McCreary would win a second Derby in 1951 aboard Count Turf.
- Mine That Bird, 2009, Calvin Borel, 50-to-1, 2.13. Probably the biggest upset in Kentucky Derby history, Calvin Borel rode Mine That Bird to the Derby win despite being only the 18th betting choice in the 20-horse field. As was his pattern, Borel kept his horse well back on the inside through the race’s early stages, beginning his drive at the mile mark and slipping into the lead position at the stretch. Riding the rail toward the finish, Borel pulled away to win by nearly seven lengths.
- Whirlaway, 1941, Eddie Arcaro, 3-to-1, 2.14. The betting favorite coming off a four-win season as a two-year-old, Whirlaway found himself blocked coming out of the gate. So Arcaro eased him back until asking for speed with a half mile to go. He got it; Whirlaway powered into the lead as the stretch run began and left no doubt, winning by eight lengths. He and Arcaro went on to complete the Triple Crown.
- Secretariat, 1973, Ron Turcotte, 1.5-to-1, 2.15. Rated easily by Turcotte at the start, Secretariat disdained the rail for the clear outside lane, which he used to rein in his competitors down the backstretch. He caught the front-runner, Sham, just past the mile marker, and won by three lengths. Secretariat of course went on to win the Triple Crown, an achievement capped by his stunning 31-length win in the Belmont stakes.
- Assault, 1946, Warren Mehrtens, 8-to-1, 2.191. The son of 1936 Kentucky Derby and Preakness winner Bold venture, Assault made his reputation with a dominant performance at the Derby. Guided by Warren Mehrtens, Assault stayed close to Spy Song until passing him for the stretch run. The final quarter mile was a pure exhibition, Assault steadily pulling away to an eight-length victory. He would go on to claim the Triple Crown.
1: War Admiral, Charles Kurtsinger, 1937, 1.6-to-1, 2.193. Son of the legendary Man O’ War, War Admiral had been lightly raced, a fact that did not deter betters from making him nearly an even-money favorite. Leading virtually start to finish, he ran easily until the final half mile when – facing a persistent challenge from Pompoon – Kurtsinger asked for speed. War Admiral maintained his two-length lead to the finish, he and Pompoon leaving the rest of the 20-horse field eight to 10 lengths and more in arrears. The subsequent Triple Crown winner, War Admiral is perhaps best-known today for his 1938 match race against Seabiscuit.