The Best Trainers Who Haven’t Won the Kentucky Derby

Racing
Champion Good Magic breezes at Churchill Downs prior to the 2018 Kentucky Derby. The colt, trained by four-time Eclipse Award winner Chad Brown, finished second to eventual Triple Crown winner Justify. (Eclipse Sportswire)

Every trainer dreams of winning the Kentucky Derby Presented by Woodford Reserve. Since the first edition in 1875, 114 trainers have won the run for the roses, with Ben Jones and Bob Baffert tied for the most at six wins apiece.

For every great trainer who has won the Derby, there are plenty more who are not on the list of Derby winners, although it’s not from lack of trying. Let’s take a look at some of the best trainers without a Derby win on their résumé, listed in alphabetical order.

All Equibase statistics for active trainers are as of the end of the day on April 11, 2021.


STEVE ASMUSSEN

CAREER WINS: 9,282

CAREER EARNINGS: $352,074,694

NUMBER OF DERBY STARTERS: 21

BEST DERBY FINISH: 2nd with Nehro in 2011 and with Lookin At Lee in 2017

Eclipse Sportswire

At some point this year, Steve Asmussen will become the all-time leading trainer in American racing history. His 9,282 wins as of April 11 are only 163 behind Dale Baird. Since he started training in 1986, Asmussen has enjoyed great success at all levels of the sport. He continues to be a force to be reckoned with in the Midwest, having recently won the training title at Sam Houston Race Park while leading the standings at the ongoing Oaklawn Park meet. Last year, he surpassed Dale Romans to become the all-time winningest trainer at Churchill Downs. He has been the country’s leading trainer by wins 10 times and the highest-earning trainer three times. Asmussen has won seven Breeders’ Cup races, two Preakness Stakes, and one Belmont Stakes. In 2016, Asmussen was inducted into the Racing Hall of Fame. Two horses he trained, Curlin and Rachel Alexandra, have also been inducted.

Asmussen’s first Derby trip was in 2001, when he sent out Louisiana Derby winner Fifty Stars to a ninth-place finish. Since then, Asmussen has had a bevy of starters, including at least one in eight of the past 10 years. However, he has not yet added the Derby to his expansive résumé. His 21 starters are far and away the most of any trainer without a win. This year, Asmussen will likely send Lecomte Stakes winner Midnight Bourbon and Arkansas Derby winner Super Stock to the Churchill Downs starting gate on the first Saturday in May.


CHAD BROWN

CAREER WINS: 1,939

CAREER EARNINGS: $199,291,585

NUMBER OF DERBY STARTERS: 5

BEST DERBY FINISH: 2nd with Good Magic in 2018

Eclipse Sportswire

Over the past decade, Brown has established himself as one of the country’s top trainers. In 2019, he became the third person to win the Eclipse Award for outstanding trainer four years in a row. He was the highest earning-trainer in the country each of those four years.

Most of Brown’s success has come with horses in turf races. Of his 102 Grade 1 wins to date, 82 of them have occurred on turf. With most of his focus on grass races, Brown does not produce major dirt 3-year-olds as often as other top-tier trainers, although he did campaign later-developing Cloud Computing to a win in the 2017 Preakness.

Brown’s best Derby shot came in 2018, when Good Magic went postward in the run for the roses as the sixth betting choice. He had won the Breeders’ Cup Juvenile the year before, giving Brown his second win in a dirt Breeders’ Cup dirt race (he has 15 wins overall). In the wettest Kentucky Derby in history, Good Magic rated off the pace but could not catch favorite and eventual Triple Crown winner Justify and finished second. This year, Brown is in position to saddle two Derby starters: Toyota Blue Grass Stakes runner-up Highly Motivated; and Crowded Trade, most recently third in the Wood Memorial Stakes Presented by Resorts World Casino.


BOBBY FRANKEL

CAREER WINS: 3,654

CAREER EARNINGS: $227,912,709

NUMBER OF DERBY STARTERS: 8

BEST DERBY FINISH: 2nd with Aptitude in 2000 and with Empire Maker in 2003

Anne Eberhardt/BloodHorse

For more than four decades, the late Bobby Frankel was one of the country’s preeminent trainers. Although based in Southern California, Frankel enjoyed success in stakes races in all areas of the country. In 1995, he was inducted into the Racing Hall of Fame, and he hadn’t done his best work yet. He won the Eclipse Award as outstanding trainer every year from 2000 to 2003, becoming the first trainer to do so.

Frankel’s first two Derby starters came in 1990, when he sent out longshots Burnt Hills and Pendleton Ridge, the latter of whom was a maiden. Both of them finished well behind the winner, Unbridled, and it was a decade before Frankel returned to the Derby. He finished second in the 2000 Derby with Aptitude and then was fourth in 2002 with Medaglia d’Oro.

In 2003, Frankel looked like he was on the doorstep of a Derby win. He sent out heavy favorite Empire Maker, who had won the Florida Derby by 9 ¾ lengths and the Wood Memorial handily. However, the big colt dealt with foot problems the week of the race, which at one point put his status in jeopardy. Frankel got the big favorite to the race, but he ended up second behind Funny Cide. Another Frankel trainee, Peace Rules, finished third. Five weeks later in the Belmont Stakes, a fully-healed Empire Maker denied Funny Cide the Triple Crown and gave Frankel his lone win in a Triple Crown race.


JERRY HOLLENDORFER

CAREER WINS: 7,678

CAREER EARNINGS: $202,842,768

NUMBER OF DERBY STARTERS: 7

BEST DERBY FINISH: 3rd with Battle of Midway in 2017

Eclipse Sportswire

Few trainers have dominated a region of the country the way Jerry Hollendorfer dominated Northern California for much of his career. He won 37 consecutive training titles at Bay Meadows and 32 straight at Golden Gate Fields. He’s won the Kentucky Oaks, the filly equivalent of the Kentucky Derby, three times (Lite Light, owned by rapper MC Hammer, in 1991; Pike Place Dancer in 1996; Blind Luck in 2010). Other great horses he’s trained include Songbird, Hystericalady, and Shared Belief. His 7,678 career wins and counting rank third on the all-time list for American trainers. In 2011, he was inducted into the Racing Hall of Fame.

Hollendorfer’s first trip to the Derby came in 2003, when he sent out longshot Eye of the Tiger to a fifth-place finish. None of his Derby starters overall has been well-regarded in the wagering, but several of them have outran their odds. In 2017, Battle of Midway gave Hollendorfer his best Derby finish, getting third at 40-1. The year after, Instilled Regard was fourth at 85.10-1.

So far, Hollendorfer’s best Derby chances never made the starting gate on the first Saturday in May. In 1998, Event of the Year started his career a perfect 4-for-4 and looked like a major Derby prospect after he won the Jim Beam Stakes at Turfway Park by five lengths. Unfortunately, he suffered a knee injury before the big race and was sidelined for more than six months. Shared Belief also looked like a serious threat after winning the 2013 CashCall Hollywood Futurity impressively, a victory that earned him the Eclipse Award as champion 2-year-old male. An abscess knocked him off the Derby trail but Shared Belief bounced back with three Grade 1 wins later in the year.


HIRSCH JACOBS

CAREER WINS: 3,596

CAREER EARNINGS: $15,356,904

NUMBER OF DERBY STARTERS: 6

BEST DERBY FINISH: 3rd with Palestinian in 1949

Paul Schafer/NYRA

For decades, Hirsch Jacobs was a force to be reckoned with in training and breeding. As a trainer, he was dominant, winning 11 national training titles in 12 years from 1933 to 1944. Later in his career, he led the country in purse earnings three times.

Although Jacobs was best-known as a claiming trainer, later in life he enjoyed success with top-class horses as well. His greatest horse, Stymie, was claimed by Jacobs for $1,500 at Belmont Park in June of 1943 and went on to become one of the top horses of the 1940s. When he retired, Stymie was the highest-earning horse in North American history with career earnings of more than $918,000.

Jacobs also enjoyed success as a breeder. Along with partner Isidor Bieber, Jacobs bred 47 stakes winners and were the leading breeders in the country four times. The operation produced several champions, including perhaps Jacobs’ best Derby hope, Hail to Reason. As a 2-year-old in 1960, Hail to Reason won seven stakes races before suffering a career-ending injury in a workout in September. He went on to become an influential sire.

At the time of Jacobs’s passing in 1970, he was the all-time winningest trainer in North American racing history. Later that year, his son John trained Personality (a daughter of Hail to Reason) to a Preakness Stakes win and a share of the Horse of the Year title.


ALLEN JERKENS

CAREER WINS: 3,859

CAREER EARNINGS: $103,754,915

NUMBER OF DERBY STARTERS: 3

BEST DERBY FINISH: 6th with Sensitive Prince in 1978

Allen Jerkens (1929-2015) was known as the “Giant Killer” for his propensity to spring upsets in big stakes races. Perhaps his most famous one came in the 1973 Whitney Handicap when he sent Onion to a surprising win over Secretariat. Jerkens won 14 training titles at New York tracks, including four at Saratoga. In 1973, he won the Eclipse Award as outstanding trainer and became the youngest trainer inducted into the Hall of Fame in 1975.

Despite his great success in other areas of the sport, Jerkens was rarely a serious threat at the Derby. His first Derby starter, longshot Round Stake, was a nonthreatening 11th in 1975. Sensitive Prince finished sixth behind Affirmed and Alydar in 1978, and perhaps his best hope, Wood Memorial winner and eventual multi-millionaire Devil His Due, was 12th in 1992. He had several Belmont Stakes starters in the years thereafter, including Virginia Rapids, Best of Luck, and Limit Out, but never went back to Louisville on the first Saturday in May.


RICHARD MANDELLA

CAREER WINS: 2,207

CAREER EARNINGS: $146,144,876

NUMBER OF DERBY STARTERS: 6

BEST DERBY FINISH: 5th with Soul of the Matter in 1994

Eclipse Sportswire

Richard Mandella opened his stable in Southern California in 1976 and has been one of the top trainers in the area ever since. He’s won five training titles at various Southern California tracks, while sporting a winning percentage of at least 15% in every year but one since 1985. Some of his best horses include 1993 Horse of the Year Kotashaan and four-time champion Beholder.

Mandella set a Breeders’ Cup record in 2003 when he won four World Championship races on the one-day card at Santa Anita Park (Halfbridled, Juvenile Fillies; Action This Day, Juvenile; Johar, dead-heat win, Turf; and Pleasantly Perfect, Classic).

Mandella has not been to the Kentucky Derby since 2004, when his two starters, Action This Day and Minister Eric, were sixth and 16th, respectively. He looked poised to win his first Derby in 2019, when Omaha Beach won the San Felipe Stakes and the Arkansas Derby impressively and was pegged as the morning-line favorite by most handicappers heading into Derby week. Unfortunately, he was scratched three days before the race with an entrapped epiglottis.


RON MCANALLY

CAREER WINS: 2,591

CAREER EARNINGS: $126,160,101

NUMBER OF DERBY STARTERS: 10

BEST DERBY FINISH: 4th with Super Moment in 1980 and Water Bank in 1982

Eclipse Sportswire

Ron McAnally’s career has spanned more than six decades. He won his first race in 1958 at Hollywood Park and has operated a stable ever since. He has won the Eclipse Award as outstanding trainer three times and has won 10 training titles on the Southern California circuit. His greatest horses include two-time Horse of the Year John Henry and champion mares Bayakoa, a two-time winner of the Breeders’ Cup Distaff, and Paseana. In 1990, McAnally was inducted into the Racing Hall of Fame.

The overwhelming majority of McAnally’s success has come with older horses. His last graded stakes triumph in a 3-year-old dirt race was in the 2004 Fantasy Stakes, when he saddled House of Fortune to victory. In 1976, McAnally won the Santa Anita Derby with An Act but elected not to send him to Louisville. His first Derby starter, Super Moment in 1980, finished fourth behind the filly Genuine Risk. Water Bank was fourth to Gato Del Sol two years later. Perhaps the best horse McAnally ever sent to Louisville, Hawkster, finished fifth in 1989 and went on to great success in turf races.

This year, McAnally will be represented at the Kentucky Derby as a breeder. He and wife Debbie bred Runhappy Santa Anita Derby winner Rock Your World in Kentucky. The colt, who figures to be one of the top four or five betting choices in the Kentucky Derby is by Candy Ride and out of the McAnallys’ mare Charm the Maker.


JOHN NERUD

CAREER WINS: 1,007

CAREER EARNINGS: $9,610,076

NUMBER OF DERBY STARTERS: 1

BEST DERBY FINISH: 2nd with Gallant Man in 1957

NYRA Photo

No one on this list came closer to winning the Derby than John Nerud. In 1957, he looked as if he was going to win the race with Gallant Man, who was clear of the rest of the field coming down to the wire. Unfortunately, jockey Bill Shoemaker misjudged the finish line and stood up in the saddle a sixteenth of a mile too soon. Iron Leige rallied in the last stride to win by a nose and deny Gallant Man the Derby.

Undeterred, Gallant Man went on to set the track record in the Belmont Stakes and become one of many champions trained by Nerud. As the trainer, president, and general manager of Tartan Farms, Nerud was instrumental in the development of many great horses. His best horse, Dr. Fager, was voted Horse of the Year in 1968 following a campaign that included seven stakes wins and three track record equaling or breaking performances. He won the Gotham Stakes in April 1967 but was held out of the Derby as Nerud did not feel he was ready to run 1 ¼ miles.

Although he retired from training in 1979, Nerud continued to have an influence on the sport for decades. He was one of the founding members of the Breeders’ Cup and was essential in selling the concept to horsemen. In 1985, he won the second Breeders’ Cup Mile with homebred Cozzene, a horse trained by his son Jan.

Nerud was inducted into the Racing Hall of Fame in 1972. He died in 2015 at the age of 102.


FRANK WHITELEY JR.

CAREER WINS: 848

CAREER EARNINGS: $8,994,619

NUMBER OF DERBY STARTERS: 2

BEST DERBY FINISH: 3rd with Tom Rolfe in 1965 and Damascus in 1967

Frank Whiteley (1915-2008) was one of the sport’s dominant trainers throughout the late 1960s and 1970s. In addition to champions Damascus and Tom Rolfe, he trained the great filly Ruffian as well as three-time Horse of the Year Forego in the latter half of the great gelding’s career.

Although Whiteley only sent two horses to the Derby, both went into the big race as serious contenders. Tom Rolfe was 5.60-1 in the 1965 Derby off three impressive victories in a row, but he finished third. The colt went on to win the Preakness Stakes two weeks later and won four more major races later that season to claim the 3-year-old male championship. Two years later, Damascus was the 1.70-1 favorite in the Derby but could not get by the leaders in the stretch and finished third. Later that year, he won the Preakness and the Belmont as well as six other major stakes en route to the Horse of the Year title and a place as one of racing’s all-time greats. Damascus was inducted into the Hall of Fame in 1974; his trainer followed suit four years later.

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