Picking the most dramatic finishes in the Kentucky Derby is all but impossible. Arguably, each of the 150 editions had a remarkable ending, and it should be no different on Saturday.
From breathtaking duels to the wire (Grindstone-Cavonnier; Mystik Dan-Sierra Leone-Forever Young) to almost unthinkable upsets (Rich Strike at 80-1; Giacomo at 50-1) to completely overpowering victories (Whirlaway by eight lengths; Barbaro by 6½ lengths), there’s good reason the Kentucky 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 150,000 racing fans roaring at the top of their lungs.
And we’re off, with a bunch of notable dramatic finishes:
On the day before the race, Rich Strike moved into the field (Ethereal Road scratched) and was a Kentucky Derby betting afterthought. He was sent off at 80-1 – the longest shot in the field – and started from the outside No. 20 post. No problem. Ridden by little-known Sonny Leon, Rich Strike was
at the back of the pack, 15th after a mile, but weaved his way through the field, moved to the rail in the final sixteenth, and stunned favorite Epicenter by three-quarters of a length. It was the second biggest upset in Kentucky Derby history – the winner returned $163.60 on a $2 win bet.
“When I was in the last 70 yards, I said 'I think I've got this race,’ ‘’ Leon said.
The drama came after the race, in which Maximum Security finished first (by 1 ¾ lengths), but jockey Flavien Prat aboard second-place Country House lodged an objection. An agonizing 22 minutes passed before the stewards did the unthinkable – disqualified Maximum Security and declared Country House at 65-1 odds, the official winner. It was the first time in Kentucky Derby history that the first-place finisher has been DQ’d for a racing infraction (interference with several horses in the stretch).
Note: There was a DQ in 2021, when Medina Spirit finished first but was DQ’d a week later following a post-race test that found a race-day overage of a medication. Runner-up Mandaloun was declared the official winner.
Four years after Giacomo’s mind-blowing 50-1 upset (yes, it was dramatic), this one seemed even more incredible. Mine That Bird barely qualified for the Kentucky 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 beat. 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, in his first Derby, thought he won. Lukas wasn’t sure. The photo finish review took several minutes. The nod went to Grindstone. Five days later, the colt was retired with an injury.
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. 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.
This was supposed to be a cakewalk for Native Dancer, who came into the race with a 9-for-9 record, a 2-year-old championship, and a Horse of the Year award. Known as the “Grey Ghost” for his striking gray coat, Native Dancer was sent off at 7-10. The race did not start well as Native Dancer was roughed up and dropped back under jockey Eric Guerin. Dark Star, at 24-1, led early and remained in front into the stretch. Native Dancer was rolling by that point, closing fast, but Dark Star 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.
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 position. However, he 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 was 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.
