Bold Ruler, Gen. Duke, Iron Liege, and Gallant Man came into Kentucky for a Derby showdown, but the Duke's injury kept him out and a riding mistake let Iron Liege in.
Bill "Willie" Shoemaker eventually won four Kentucky Derbies, five Belmont Stakes, and two Preakness Stakes. He saddled up from 1949 through 1990, setting a longevity standard for jockeys. He amassed 8,833 wins on greats such as Swaps, Spectacular Bid, Round Table, Buckpasser, Northern Dancer, John Henry, Forego and others. In 1958, he was inducted into the jockeys Hall of Fame.
In 1957, a riding mistake forever attached an asterick to his otherwise top notch career. A moment of lost concentration overcame him and created a Kentucky Derby memory still talked about today.
The foals of 1954 were to become a top class act. They included Bold Ruler, who would sire Secretariat, Round Table, who would win over forty races, Gallant Man, Iron Liege, and Gen. Duke, all top runners. Bold Rulers continue to be great racers. Many stakes winners were also sired by the 1957 Derby participants.
Bold Ruler set two track records before the Derby, at Hialeah in the Flamingo Stakes (1:47) and in the Wood Memorial (1:48-4/5). Round Table shattered the Keeneland nine furlong record in the Blue Grass Stakes, finishing in 1:47-2/5.
Contenders Federal Hill and Gen. Duke set and matched world records for six and a half furlongs at 1:15 (Gulfstream Park) and for nine furlongs in the Florida Derby at 1:46-4/5, respectively.
Gallant Man ran down Gen. Duke by six lengths at Tropical Park and equalled the track record for six furlongs. Iron Liege topped his stablemate, Gen. Duke, twice in record times for 1-1/16 miles and for seven furlongs.
Undoubtedly, it would be a derby duked out by speedsters.
Before the Derby could be turned over to the speed demons, however, Gallant Man's regular jockey, John Choquette, was suspended for rough riding. Trainer John Nerud turned to one of the rising stars beginning to replace the boots of Eddie Arcaro, Johnny Longden, and others, Bill Shoemaker, who quickly accepted the mount.
In a note of historic irony, Sports Illustrated, had been following the career of Iron Liege. Their story pitch had been to photograph the delivery of a foal (compliments of the mighty Calumet Farm) and to follow the foal's progress into his third year. By Derby day, Iron Liege was a 15-1 choice.
Iron Liege's sire was Bull Lea, also daddy to Armed, Bewitch, Citation, Coaltown, Two Lea, and Hill Gail. Calumet's Derby day seemed to rest on good hooves. That was until Gen. Duke bruised one. The injury scratched him from the Derby contenders list and left Bold Ruler to emerge as the favorite.
The Derby field of nine got a good break, with Federal Hill surging to the front. Iron Liege, with Bill Hartack aboard, held the third position, with Bold Ruler second and Round Table fourth at the half mile marker.
Shoemaker and Gallant Man traveled comfortably in fifth position.
Into the stretch run, Iron Liege took the lead, while Gallant Man picked his way to the second spot. Just as it appeared that Gallant Man would smother Iron Liege for the lead and probably win the race, Shoemaker inexplicably stood up in the stirrups, apparently thinking Gallant Man had found the wire and the Derby championship.
Just as quickly, realizing his mistake, Shoemaker sank back down in the saddle to finish. It was too late. Iron Liege and Hartack had swept past and put the runner's nose first at the wire in the closest Derby finish since 1933 when the jockeys of Broker's Tip and Head Play pulled each other to the finish line.
In its official race review, the Daily Racing Form reported that Gallant Man's "rider misjudged the finish line", allowing Iron Liege to win.
Shoemaker and Gallant Man got over it. They won the third and final Triple Crown race, the Belmont Stakes, five weeks later.