Once isn't enough: Meet multiple Kentucky Derby-winning trainers

In two weeks, 3-year olds will contest the biggest prize in North America in the 2018 Kentucky Derby. Of the 22,500 Thoroughbreds born on the continent in 2015, a single horse from that crop will lay claim to being the winner.

Winning America’s most prestigious classic event is the holy grail for trainers who have thrown a saddle on a horse and legged up a jockey. It's the pinnacle achievement in the profession interlocking with a "cloud nine" occasion. It's also a magnet for attracting new clientele.

While the majority of trainers continue to chase the prize year after year, pinning their hopes on one of their equine candidates to make the dream a reality, even if only once, several trainers both past and present have been fortunate enough to taste Derby victory on more than one occasion.

The names below are those trainers with multiple Derby wins. Six have accomplished the feat in back-to-back years. 

Three or more Derby wins

Ben Jones - Tops the list with six Kentucky Derby winners. The first came in 1938 with Lawrin. The following year, Jones was hired by the dominant Calumet Farm operation and trained five Derby winners for the renowned owner: Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949) and Hill Gail (1952). Both Whirlaway and Citation won the Triple Crown. His training career spanned more than four and a half decades.

Bob Baffert - One of three trainers with four Kentucky Derby winners: Silver Charm (1997), Real Quiet (1998), War Emblem (2002) and Triple Crown winner, American Pharoah (2015). Baffert got his start on the quarter horse circuit, where he had plenty of success. Following the segue to thoroughbreds, Baffert became a household name as prosperity continued with numerous major stakes victories and a multitude of awards. He looks to secure second-place on the list all to himself this year as he readies Solomini and probable Derby favorite Justify for a shot at glory.

D. Wayne Lukas - Another with four Kentucky Derby winners: Winning Colors (1988), Thunder Gulch (1995), Grindstone (1996) and Charismatic (1999). As with his counterpart above, the 82-year old Lukas began training quarter horses before switching over to the thoroughbred world. With an abundance of victories, awards, records and earnings achieved, he is the most successful trainer in the history of the sport. He too is looking for a fifth Derby, sending out Bravazo in this year’s edition.

Herbert ‘Henry’ Thompson - Completes the trio of trainers with four Kentucky Derby winners: Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932) and Brokers Tip (1933). All winners were for owner Colonel E.R. Bradley, who started 28 Derby runners and every name began with the letter "B." Of his four winners, the one most distinguishable for Thompson is the notorious “Fighting Finish” of 1933 featuring Brokers Tip.

James "Sunny Jim" Fitzsimmons - One of two trainers with three Kentucky Derby winners: Gallant Fox (1930), Omaha (1935) and Johnstown (1939). The first two went on to win the Triple Crown. Fitzsimmons trained for more than seven decades and had one of the most successful careers in racing history. He was the first trainer of Seabiscuit and conditioned Nashua, who lost as the favorite in the 1955 Derby. Fitzsimmons also trained Bold Ruler, the sire of Secretariat.

Maximilian ‘Max’ Hirsch - Also had three Kentucky Derby winners: Bold Venture (1936), Triple Crown winner Assault (1946) and Middleground (1950). The last two horses were for King Ranch, who Hirsch trained for from the 1930’s until 1969. In a career that lasted 70 years, Hirsch saddled 1,933 winners, including his final winner eight hours before he passed away.

Two Derby wins

Lazaro ‘Laz’ Barrera – The 50-year training career of Barrera began in his home country of Cuba, continued to develop in Mexico and came to fulfillment in the United States. He won the Eclipse Award as the outstanding American trainer four straight years and was the nation's leading money winner five times. His pair of Derby winners were, Bold Forbes (1976) and Triple Crown winner, Affirmed (1978). 

Henry Forrest – Saddled two Kentucky Derby winners in three years, Kauai King (1966) and Forward Pass (1968). In addition to operating public a stable for many years, Henry Forrest went on to work for distinguished owners, Claiborne and Calumet Farm. It was for the latter that he trained Forward Pass. At the time of his passing, Forrest was the all-time leader in wins at both Churchill Downs and Keeneland Race Course.

LeRoy Jolley - A licensed trainer in parts of seven decades (1958 through 2017), Leroy Jolley won the 1975 Kentucky Derby with Foolish Pleasure and the 1980 edition with the filly, Genuine Risk. In between his two Derby wins, he had two second-place finishes with, Honest Pleasure (1976) and General Assembly (1979).

Horace “Jimmy” Jones – Not only did Jones train consecutive Derby winners, Iron Liege (1957) and Tim Tam (1958), he was in the Derby winners circle five other times as an assistant to his dad Ben Jones. Together, the father and son team provided owner Calumet Farm with seven Derby winners. His career spanned 60 years and he was the first trainer to win more than $1 million in purses. 

Lucien Laurin – The Canadian-born horseman had already saddled a Triple Crown race winner, Amberoid, in the 1966 Belmont Stakes well before he won the Kentucky Derby with Riva Ridge in 1972. The following year, Laurin got his second Derby win with Secretariat, who went on to become the first horse in a quarter of a century to win the Triple Crown. Lucien Laurin is also enshrined in the Canadian Horse Racing Hall of Fame.

Horatio Luro – Emigrating from Argentina to the United States, Luro toiled at several major and minor tracks honing his craft before making his way to the top of the racing world. "El Grand Senor," as he was better known in the industry, trained two colts, California-bred Decidedly (1962) and Canadian-bred Northern Dancer (1964), who were successful in the Run for the Roses. Luro is also a member of the Canadian Racing Hall of Fame.

Carl Nafzger – Before he ever got involved with thoroughbreds, Nafzger started out in the rodeo circuit where he enjoyed a successful career. When the physical demands of the sport proved too much, he began training thoroughbreds in the early 1970s. As the years progressed Nafzger was able to train better horses. Has started only three horses in the Kentucky Derby, but has come away victorious in two editions: Unbridled (1990) and Street Sense (2007).                                                                                                                   

Doug O'Neill - After graduating high school, O'Neill began walking horses, eventually advancing up through the ranks. He obtained his trainers license in 1989 and soon after had his first winner, followed by many more. His prowess over the next decade attracted wealthier owners and in the early 2000's, he had built up one of the largest and most successful stables in Southern California. O'Neill has developed Eclipse Award winners, Breeders' Cup champions, and two Kentucky Derby winners, winning the roses with I'll Have Another (2012) and Nyquist (2016). 

                                                                                                    
Todd Pletcher – Worked under the tutelage of D. Wayne Lukas before branching out on his own in the mid 1990s. Has amassed multiple training titles and holds the all-time record for purse earnings. Since his first appearance in the Kentucky Derby in 2000, Pletcher has been represented in every edition except 2003. He has prepared 48 starters in 17 Derbys. Went 0-for-24 before finally getting the proverbial monkey off his back in 2010 with Super Saver. He won for a second time last year with Always Dreaming. This year, with a strong quartet of horses heading to Louisville, Pletcher stands a solid chance to garner a third win.

Woodford ‘Woody’ Stephens - In a career that spanned seven decades, Stephens was one of the most accomplished trainers in the game, developing several national champions. Although he was well respected and had a solid reputation as a trainer, Stephens’ fame catapulted in the 1980s when he won an unprecedented five consecutive Belmont Stakes. One of those Belmont winners, Swale (1984), brought Stephens his second Kentucky Derby win. Ten years earlier, Stephens saddled Cannonade in the centennial Kentucky Derby for his first Derby winner.

Charles Whittingham - The most successful trainer in Santa Anita history joined up with trainer Horatio Luro, who employed him from 1940 until 1950 as his assistant, before Whittingham opened his own public stable. When his illustrious career ended in 1999, the "Bald Eagle" as Charlie was often referred to, had won over 2,500 races, collected various awards and trained champions, including Kentucky Derby winners Ferdinand (1986) and Sunday Silence (1989), both of which made him the oldest trainer of a Derby winner.

Nicholas Zito – The New York native learned the training occupation under Leroy Jolley and Johnny Campo, the latter trained Derby champ Pleasant Colony (1981). A year after his training career began in 1972, Zito recorded his first win and 46 years later, the 70-year old conditioner has exceeded 2,000 wins. Among those career triumphs include a pair of Kentucky Derby scores with Strike the Gold (1991) and Go for Gin (1994).