Kentucky Derby Lucky Losers: Bold Ruler (1957)

Oct 29, 2025 Jennifer Kelly

Roses at the Kentucky Derby (Photo by Coady Photography/Churchill Downs)

The 1957 Kentucky Derby might be best known for Bill Shoemaker’s misjudging the finish line at Churchill Downs: his hesitation with a sixteenth of a mile to go gave Bill Hartack on Iron Liege the chance to make up enough ground to beat Shoemaker and Gallant Man by a nose. Fourth in the 83rd edition was a colt whose fame stretched far beyond his losing turn beneath the Twin Spires.

Bold Ruler may not have worn roses that day, but this Lucky Loser went on to have a stellar racing career, winning 23 of his 33 races, and then passed on that ability to his legion of progeny, including one legend who wore a crown – a Triple Crown.

Royal Roots

The Aga Khan’s Mumtaz Begum may have raced only at two, but as a broodmare, she followed in her dam Mumtaz Mahal’s footsteps and produced a star in Nasrullah. Bred and owned by the Aga Khan, the spiritual leader of the Shia Ismaili Muslims, Nasrullah was a stakes winner in England and then stood stud in both England and Ireland. In 1950, Arthur B. “Bull” Hancock paid £150,000 (reported as $340,000 in Ed Bowen’s book on Bold Ruler) for the son of Italian star Nearco and sent him stateside to Claiborne Farm.

At Claiborne, Nasrullah produced dual classic winner Nashua, bred by William Woodward right before his death; Never Say Die, 1954 Epsom Derby winner; and a bay colt with a diamond-shaped smudge of white in his forehead, Bold Ruler. Bred at Claiborne Farm, the new colt’s dam, Miss Disco, was a product of Hall of Famer Discovery and stakes winner Outdone. Winner of the Test Stakes at Saratoga, Miss Disco had been bred by Alfred Vanderbilt, who sold her as a yearling in 1945. She raced for Sydney Schupper, who sold her as a broodmare prospect to Arthur “Bull” Hancock of Claiborne Farm. He offered her to Gladys Mills Phipps of Wheatley Stable, who then took Hancock up on his recommendation to breed Miss Disco to Nasrullah. That pairing yielded not just Bold Ruler, but also American Grand National winner Independence.

Mrs. Phipps sent her purple-pedigreed colt to the Wheatley Stable trainer, the legendary “Sunny Jim” Fitzsimmons. The former jockey turned conditioner had been training for Wheatley since the late 1920s, working only for the Phippses and William Woodward for decades. His experience preparing both Gallant Fox and Omaha for their respective Triple Crowns made Fitzsimmons the right man for the talented Nasrullah colt.

Regal Racehorse

The thing about Bold Ruler was that he seemed to be beleaguered by incidental injuries that caused problems later on. He fought the chain that linked his halter to the wall during training one day, lacerating his tongue and leaving a sensitivity that persisted through his racing career. He slammed into the gate in the Juvenile Stakes, hurting his back, and then in his Futurity prep, his head hit the gate at the break, and he returned with a bloody mouth. Nevertheless, Bold Ruler won his first five races at two, including the Juvenile, and then added the Futurity for a record of seven wins in 10 starts in 1956.

This brings us to 1957 and the Nasrullah colt’s date with one infamous Run for the Roses. He started the new season with a win in the Bahamas at Hialeah, then finished second in the Everglades, won the Flamingo, and then logged a second in the Florida Derby. Facing a field that included Gallant Man in the Wood Memorial, Bold Ruler passed him late to win the race by a nose. That led up to a confrontation between the two in Louisville. Joining them were Calumet’s Iron Liege, Round Table, and Better Bee, future sire of Bee Bee Bee, 1972 Preakness winner.

While the drama between Gallant Man and Iron Liege played out in the stretch, Bold Ruler lingered back in fourth. He had lingered just off the pace early and then, as the form chart put it, “failed to stay when set down through the stretch.” This and other performances led to the assumption that the son of Nasrullah could not stay past a mile, though his past performances say otherwise. Bold Ruler followed his turn in the Kentucky Derby with a win in a 1 1/16-mile allowance at Pimlico before trying the 1 3/16-mile Preakness Stakes on May 18. He beat Iron Liege by two lengths that day and then finished third behind Gallant Man in the 1 1/2-mile Belmont Stakes.

The rest of his three-year-old season was a winning one. Contesting stakes from six to 10 furlongs, Bold Ruler took six of seven starts, his lone loss in the Woodward. His four-year-old season promised more of the same greatness, but a wrenched ankle preparing for the Widener Handicap in February put off his 1958 debut until the Toboggan at Belmont Park in mid-May. Carrying 133 pounds, the Nasrullah colt won the six-furlong handicap on the straight Widener course by a half-length. He followed that with a win in the seven-furlong Carter before tackling the great New York handicaps.

With 135 pounds and regular rider Eddie Arcaro, he finished second to Gallant Man in the one-mile Metropolitan Handicap and then won the 10-furlong Suburban by a nose. In between those two races, he took the Stymie Handicap, too. He won the Monmouth Handicap with ease and then tried the 1 3/16-mile Brooklyn Handicap. Bold Ruler had won at that distance in the Preakness the year before, but then he carried 126 pounds, not the 136 that his record earned him. Bursitis in that previously wrenched ankle, plus the weight impost, proved too much for the future Hall of Famer. He was retired to stud at Claiborne Farm, where he stood until he died in 1971, a year after his most accomplished son was foaled at the same farm.

Racing Royalty

In his 12 seasons as a stallion, Bold Ruler has 366 named foals, with 240 winners and 82 stakes winners. He produced stakes winners like Lamb Chop, Successor, Gamely, Wajima, and Bold Bidder, who later would sire classic winners like Cannonade and Spectacular Bid. However, that most accomplished son came in 1970, a chestnut foal out of the Princequillo mare Somethingroyal. Secretariat was Horse of the Year at both two and three, ending the 25-year Triple Crown drought with his record-breaking performances in all three classics. Not only did he follow his sire's footsteps into the Hall of Fame, but Secretariat became a sire of champions like Risen Star and Lady’s Secret and then the broodmare sire of A.P. Indy, Gone West, Summer Squall, Storm Cat, and more.

It's #BelmontStakes Day!! 🤩

Did you know that along with the largest winning margin, Secretariat also holds the record for the fastest time? 🏇

In 1973, he ran the 1 1/2-mile race in 2:24.00 minutes. ⏱️ pic.twitter.com/vu1sbmUqY8

— TwinSpires Racing 🏇 (@TwinSpires) June 10, 2023

Though he might have been out of the money on Derby Day, Bold Ruler left his legacy on the Run for the Roses with sons like Secretariat and Bold Bidder, sealing his name in the pantheon of Thoroughbred greats on the track and off.