Picking the most dramatic finishes in the Kentucky Derby is all but impossible. Arguably, each of the 141 editions has a remarkable ending, and Saturday’s should be no different.
From breathtaking duels to the wire (Grindstone-Cavonnier) to almost unthinkable upsets (Mine That Bird at 50-1) to completely overpowering victories (Barbaro by 6 ½ lengths), there’s good reason the Derby is often called the greatest two minutes in sports.
For many, though, it’s all about how the race unfolds once these 3-year-olds come hauling around the turn and into the stretch under the twin spires at Churchill Downs with 170,000 racing fans roaring at the top of their lungs.
And we’re off, with a handful of dramatic finishes:
MINE THAT BIRD (2009)
Four years earlier, Giacomo had pulled off a stunner at 50-1 odds, but this one seemed even more incredible. Mine That Bird barely qualified for the Derby, and little-known trainer Chip Woolley – a cast on his broken leg and all – hooked a horse trailer to his truck and drove 1,200 miles from New Mexico to Churchill Downs. Over a sloppy track, jockey Calvin Borel weaved his horse from last place past 18 others, moved rapidly to the inside and, before race caller Tom Durkin could get the words out of his mouth, the Bird was in front by three lengths along the rail on his way to a 6 ¾-length win. …. “Right there on the inside, coming through, Mine That Bird!” Durkin intoned. “In a spectacular, spectacular upset, Mine That Bird has won the Kentucky Derby! An impossible result here!” A $2 win ticket was worth $103.20.
For Triple Crown winning trainer Bob Baffert, this still stands as his toughest loss. Although Unbridled’s Song was the 7-2 favorite and leading, it was Baffert’s Cavonnier who took over with a quarter-mile to go. Meanwhile, Grindstone, under Jerry Bailey, was making a huge move from 15th place and by the time they flashed by the finish line, it was too close to call between trainer D. Wayne Lukas’ Grindstone and Cavonnier. Baffert thought he won. Lukas wasn’t sure. The photo finish review took a long time. Several minutes. The nod went to Grindstone. Five days later, the colt was retired with an injury.
IRON LIEGE (1957)
Still hard to believe the great Bill Shoemaker could misjudge the finish line, causing Gallant Man an almost sure victory. But it happened.
A stellar field included Bold Ruler and Round Table, but it was Gallant Man and Iron Liege dueling to the wire in the stretch. Racing neck-and-neck into deep stretch, Shoemaker stood up in the saddle to celebrate victory too early – clearly misjudging the finish line. Gallant Man briefly lost momentum, and Bill Hartack aboard Iron Liege held on to win by a neck.
DARK STAR (1953)
This was supposed to be cakewalk for Native Dancer, who came into the race with a 9-for-9 record, a 2-year-old championship and a Hose of the Year award. Known as the “Grey Ghost” for his striking gray coat, Native Dancer was sent off as the 7-10 favorite. The race did not start well as Native Dancer was roughed up and dropped back under jockey Eric Guerin. Dark Star, a 24-1 long shot, led early on and remained in front into the stretch. Native Dancer was rolling by that point, closing fast, but Dark Star barely hung on and won by a head. Native Dancer went on to win the Preakness and Belmont Stakes and never lost again. He won 21 of 22 career races.
BROKERS TIP (1933)
Welcome to the fighting finish Derby, the one with the grabbing, pushing and whipping. The unbelievable events occurred in the stretch, and the lead roles were jockey Don Meade aboard Brokers Tip and Herb Fisher aboard Head Play. A stubborn Head Play would not load into the starting gate, and was allowed to begin the race from outside the gate. With mud on the track, Head Play stayed off the rail and led. Brokers Tip stayed well back, but the late-running colt was guided through an inside opening and Fisher steered Head Play toward Brokers Tip. Then the rumble began. With their horses racing stride for stride to the finish, the jockeys grabbed each other’s saddlecloths, bridles and legs. They used whips on each other, not their horses. They crossed the finish line together, flailing away. Brokers Tip was declared the winner by the racing stewards, who watched the race through binoculars. It was the only race Brokers Tip ever won.