At Long Last: Perseverance Pays Off at the Kentucky Derby

The Kentucky Derby (G1) is more than a race steeped in history and tradition. On the first Saturday in May, Churchill Downs’ one-mile oval becomes the stage where dreams of glory are forged and dashed in a matter of two minutes. For some, their dreams are realized sooner than others, whose journeys to the Derby winner’s circle stand as a test of endurance, resilience, and unwavering determination. 

For names like Day and Pincay, Whittingham and Stephens, and Mellon and Genter, the road to Derby glory is long and winding, but their arrival is a celebration of the triumph of spirit and perseverance that finally brought them Kentucky Derby glory. 

Pat Day

Growing up in Colorado, Patrick Alan Day learned horsemanship from his father and dreamed of being a rodeo rider. By age 20, he had traded bucking broncos for speedy racehorses, winning his first race in July 1973 at Prescott Downs in Arizona. From there, Day’s patient style of riding brought him opportunities to move his tack first to Chicago and then to New York. Within a decade, he was the nation’s winningest jockey and won the first of four Eclipse Awards for leading jockey in 1984. Day also won the inaugural Breeders’ Cup Classic (G1) on Wild Again the same year.

For the first two decades of his career, though, one goal eluded him: the Kentucky Derby. Day’s first ride in the Run for the Roses came aboard Music Leader in 1982, but they could do no better than 15th that year. He was second three years in a row, coming close to wins on Forty Niner (1988), Easy Goer (1989), and then Summer Squall (1990). Even though Day had won the Preakness (G1) with Tank’s Prospect (1985) and Summer Squall and the Belmont (G1) with Easy Goer, he had yet to visit that famed Derby winner’s circle– until he met Lil E. Tee. In a field that included juvenile star Arazi, Lil E. Tee bided his time on the backstretch, went seven-wide on the far turn, and then passed Casual Lies to win the 1992 Kentucky Derby by a length. 

In a career that spanned more than three decades, this Hall of Fame jockey won many of the sport’s biggest prizes, including 12 Breeders’ Cup races, five Preaknesses, and three Belmont Stakes. But the greatest of them all was that elusive Derby win on Lil E. Tee.

Laffit Pincay Jr.

Laffit Pincay’s boyhood dreams were not of saddles and silks but of bats and gloves. Early on, though, he realized that the growth spurt that would enable him to play baseball at a high level would elude him, so Pincay followed in his father’s footsteps and made the racetrack his home. He started riding in Panama and then came to the United States under the sponsorship of owner/breeder Fred Hooper and agent Camilo Martin. Pincay arrived in 1966 and immediately found success. 

He was leading jockey by earnings from 1970-1974 and earned the first of five Eclipse Awards in 1971. Pincay rode in his first Kentucky Derby that year, finishing fifth on Unconscious, and then was on Sham in the 1973 Triple Crown. The Panamanian native won three Belmont Stakes in a row in 1982-1984, but did not break through at Churchill Downs until 1984. He was second on Sham in 1973, General Assembly in 1979, and then Rumbo in 1980. He was nearly 20 years into his career and had not yet found his way into the Kentucky Derby winner’s circle, but a son of Triple Crown winner Seattle Slew was about to change all of that.

Swale was a dual Grade 1 winner at two and came into the 1984 Triple Crown season as one of the favorites for the Kentucky Derby. The filly Althea’s performance in the Arkansas Derby (G1) was impressive enough for her to enter the gate as the favorite while Swale went off as second choice. The filly led for the first seven furlongs with Pincay and Swale biding their time in third. As the field swung into the stretch, the son of Seattle Slew took over and moved to the rail, easily powering away to a 3 1/2-length win. 

Swale was out of the money in the Preakness, but won the Belmont Stakes, giving Pincay his third and last Test of the Champion. Though this Hall of Famer rode for another two decades with 10 more chances to win the Derby, the 1984 Derby was his only victory in this famed race.

Charlie Whittingham

When Charlie Whittingham was born on April 13, 1913, New York racing was six weeks from its revival. When he passed away on April 20, 1999, the trainer they called “The Bald Eagle” had progressed from hot walker to assistant trainer to Hall of Famer who conditioned a half-dozen fellow Hall of Famers. 

The California native started his racing career as a hot walker in Tijuana during the Great Depression and then took out his trainer’s license in 1934. He worked as an assistant trainer for Horatio Luro, the Argentinian horseman who worked with Northern Dancer, Flaming Page, and Princequillo. After serving his country in World War II, Whittingham opened his public stable in his home state of California in 1950. He would go on to dominate racing in the Golden State while eschewing the Triple Crown rat race, starting only two horses in the Kentucky Derby before coming east with Ferdinand in 1986.

His last Derby starter had been Divine Comedy, who finished ninth in 1960, so Whittingham’s presence at Churchill Downs was no fluke. Ferdinand won the Santa Catalina S., was second in the San Rafael (G2), and then finished third behind Snow Chief in the Santa Anita Derby (G1). The colt’s biggest problem was his tendency to lose focus once he was on the lead. Whittingham’s choice of jockey for the Derby, the legendary Bill Shoemaker, was the answer. After a troubled start, the Shoe positioned Ferdinand for success around the far turn, swinging four wide into the stretch and accelerating to the lead with a furlong to go. Their margin of victory was 2 1/4 lengths.

Whittingham was 73 when he entered the winner’s circle, Shoemaker 54. By 1986, “The Bald Eagle” had already been in the Hall of Fame for a dozen years and had won nearly every major California stakes race more than once. Ferdinand’s Kentucky Derby gave the legendary trainer one of the few honors that had been missing from his resume. The following year, Ferdinand’s win over the 1987 Derby-Preakness winner Alysheba added the Breeders’ Cup Classic to his laurels. 

In 1989, Sunday Silence’s Derby-Preakness wins brought Whittingham more Triple Crown glory, adding even more jewels to an already rich legacy. 

Woody Stephens 

Hall of Fame trainer Woodford Cefis “Woody” Stephens was also born in 1913, a Kentucky native who started his career in racing not as a trainer but as a jockey, groom, hot walker, and more for John Ward. In the late 1930s, he branched out as a public trainer until 1956, when he went to work for Harry Guggenheim’s Cain Hoy Stable. 

Stephens’s first four tries at the Kentucky Derby saw him finish second, third, fourth, and fifth, with Never Bend coming closest in 1963. In 1974, Stephens returned to Churchill Downs with Cannonade, a rapidly improving colt who navigated the 23-horse field to take the 100th Run for the Roses. Thirty-seven years after going out on his own, Woody had his Derby win. Two years later, he was inducted into the National Museum of Racing and Hall of Fame. 

Stephens got his second Kentucky Derby in 1984 with Swale. The Claiborne Farm colt also was one of the Hall of Famer’s record five consecutive Belmont Stakes winners, that feat alone a testament to this legendary horseman’s skills. 

Paul Mellon

The son of famed financier and Secretary of the Treasury Andrew Mellon, Paul Mellon could have done whatever he wanted with the opportunities his family’s wealth offered him. This art collector and philanthropist chose horses. 

After graduating from Yale, Mellon traveled to England to continue his education at Cambridge University. There he fell in love with horses and started his Rokeby Stable after serving in World War II. His stable included steeplechasers and flat racers; Rokeby eventually expanded to Europe as well. He also maintained a farm in Upperville, Virginia, where he bred and raised horses like Arts and Letters, Quadrangle, and Mill Reef.

Mellon’s first Derby starter was Quadrangle, who finished fifth behind Northern Dancer in 1964 and then took the Belmont and Travers. Five years later, Arts and Letters was second to Majestic Prince in the 1969 Derby before going on to win the Belmont and the Travers. Head of the River started in the Rokeby gray and yellow colors in the 1972 Run for the Roses and finished eighth, Mellon’s last Derby horse until 1993. 

The 85-year-old Mellon began dispersing his bloodstock in 1992 but held on to Sea Hero, a colt by Grade 1 winner Polish Navy out of the stakes-winning mare Glowing Tribute. The Champagne (G1) winner entered the 1993 Kentucky Derby at odds of 13-1 and showed that he had the right stuff with Jerry Bailey in the saddle. Their 2 1/2-length victory gave Mellon his one and only Kentucky Derby win after more than 60 years in racing. 

“You can’t put into words (what it means to win the Derby),” Mellon said after the race. “It’s very exciting, something that you never believe is going to happen to you until it does.”

Frances Genter

Harold and Frances Genter drove their family to Florida for a vacation, and on their way back to their Minnesota home, they decided to make a stop at Churchill Downs. It was Derby Day 1938 and Frances was smitten. Harold had developed the Toastmaster pop-up toaster and then started the Coin-Master Company, which put coin-operated washers and dryers in apartment buildings across the county. His business prowess gave the couple resources to pursue a hobby like racing, and within two years, the Genters had bought their first racehorse and began a lifetime of investment in the sport.

The Genters owned Rough n’ Tumble, 1951 Santa Anita Derby winner and sire of Hall of Famer Dr. Fager; Florida Derby and Metropolitan Handicap victor In Reality; and 1986 Breeders’ Cup Sprint (G1) champion Smile. But they did not have a Kentucky Derby starter until 1990, when Florida Derby (G1) winner Unbridled brought Frances Genter to Louisville. 

Harold had passed away in 1981, but the 92-year-old Frances returned to Churchill Downs with a solid chance at taking home the roses. Her petite frame and poor eyesight made it difficult for her to see what was happening on the track, so trainer Carl Nafzger narrated the action for her in a memorable stretch run that touched the hearts of millions. The former rodeo rider turned conditioner hurried to the winner’s circle to stall the festivities until Genter could make her way to the trophy presentation, her reward for more than 50 years of joy in the sport of horse racing.