Biggest Triple Crown upsets: 5 Derby, 5 Preakness, 5 Belmont

Biggest Triple Crown upsets: 5 Derby, 5 Preakness, 5 Belmont
Photo: Churchill Downs / Kentucky Derby Media Guide

At 80-1, Rich Strike was not the longest shot ever to win the Kentucky Derby, but he was the one whose shocking victory resonated the fastest.

The only bigger betting surprise to win the race was Donerail, who carried odds of 91-1 in 1913. Not only was that before the internet made communications faster than the blink of an eye, it was more than a decade before radios became commonplace in American homes. Aside from the 30,000 people at the track and anyone who heard via word of mouth, it would not be until the following day’s newspapers when most Americans found out about Donerail.

A $2 win bet back then would be worth about $58 now. The $184.90 payback would be $5,400 today.

Nowadays the amazement about big long shots is instant and global. Some stand the test of time better than others. These were the biggest upsets in Triple Crown history – race by race.

Kentucky Derby

Donerail (91-1), 1913. After going 4-for-18, Donerail was 0-for-3 as a 3-year-old coming into the Derby. The losing streak left owner-breeder-trainer Thomas Hayes reluctant to enter the Derby, but he was talked into it by jockey Roscoe Goose and a close friend who put $100 on Donerail at bookmaker’s odds of 100-1. With space at a premium in the Churchill Downs barns, Donerail was stabled three miles south at Douglas Park. On race day he had to be walked over the unpaved streets on the edge of Louisville to get to the track. The 6-5 favorite Ten Point established a blistering pace (look familiar?) but held his own until Goose used rigorous urging in the homestretch to rally Donerail from fifth to first. The winning 2:04.8 time was the fastest of the first 18 runnings of the 1 1/4-mile Derby.

Rich Strike (80-1), 2022. These are the bullet points of a story that has been told countless times since May 7. The Keen Ice colt broke his maiden by 17 lengths late last summer at Churchill Downs and was claimed for $30,000 by trainer Eric Reed for owner Rick Dawson. Even though he lost his next five races, Rich Strike earned enough qualifying points to become the fourth also-eligible horse for the Derby. Three horses were withdrawn, and only minutes before the deadline on the eve of the race, D. Wayne Lukas scratched Ethereal Road. Rich Strike was in the Derby. From the outside post, jockey Sonny León bided his time behind a record-setting early pace, rallied Rich Strike from 15th place in the last quarter-mile and passed the favored Epicenter in the last 10 strides to score the unlikely upset.

Country House (65-1), 2019. On a rainy day, it took 22 minutes for Kentucky stewards to decide that first-place finisher Maximum Security had interfered with three other horses near the five-sixteenths pole on a sloppy track. When Max came down, up went the No. 20 of the Lookin At Lucky colt who was not directly affected by all the commotion in the second turn. The controversial decision brought Hall of Fame trainer Bill Mott and jockey Flavien Prat their first Derby win. Country House, a closer whose only other win came in a maiden race during the Gulfstream Park winter, came down with a lung infection after the Derby. Then came foot trouble, and he never raced again. He stands as a stallion at Darby Dan Farm in Lexington.

Mine That Bird (50-1), 2009. Just like Rich Strike, Mine That Bird got a ground-saving trip and made a deep-closing run along the rail to pull off what was then the most startling Derby victory in 96 years. Before Calvin Borel’s daring ride, the little gelding by Birdstone was a Canadian champion as a 2-year-old, but he finished last in the Breeders’ Cup Juvenile at Santa Anita. In 2009 he was on his third trainer, Chip Woolley, when he finished second and fourth in a pair of stakes at Sunland Park in New Mexico. After his shocker at Churchill Downs, Mine That Bird came within a length of beating eventual horse of the year Rachel Alexandra in the Preakness. That was as close as he came to winning the rest of his career.

Giacomo (50-1), 2005. Yet another closer (see a pattern here?), the Holy Bull colt broke his maiden on his second try in Southern California. He seemed to suffer from second- or third-itis after that. Then he finished fourth in the Santa Anita Derby (G1), so he was a bettor’s afterthought in a year when West Coast horses were lightly regarded. None was shorter than 21-1 in the Derby. Behind a fast pace, jockey Mike Smith bided his time in 18th place before taking a wide turn for home, urging Giacomo into the lead with 70 yards to go on the way to a shocking win. That put John Shirreffs, a Vietnam War veteran, on the training map. Giacomo won once more before being retired after his 4-year-old season. After stallion duty at farms in Kentucky and California, he stands now at Oakhurst Equine in Oregon.

Preakness Stakes

Master Derby (23-1), 1975. In a race that has been won exactly half the time by favorites and with smaller fields, it is no wonder that the longest shot to win the Preakness was “only” 23-1. Master Derby, a Dust Commander colt, had been a 5-1 disappointment finishing fourth to Foolish Pleasure at Churchill Downs. He was supplemented into the 100th Preakness, where bettors were not counting on jockey Darrel McHargue’s smart, stalking trip for trainer Smiley Adams. Master Derby took the lead turning into the stretch, drifted late into the path of the oncoming Foolish Pleasure, finished first by a length and survived an objection to win the race. Previously a winner in the Louisiana Derby (G2) and Blue Grass (G1), Master Derby never had that big a score again. He was retired in the summer of 1976 and went on to a stud career before dying in 1999.

Coventry (21-1), 1925. This was a story that could have gone terribly wrong. Coventry was an 0-for-3 maiden coming into the Preakness. The day before he won what was the year’s first classic, he bowed a tendon. Trainer Bill Duke decided the injury was not very bad, so the Negofol colt went to post as the third-longest shot in the field of 12. Jockey Clarence Kummer stayed within 3 1/2 lengths of the lead throughout the race, accelerated in the stretch and won by four lengths. The chart said Coventry “eased up” at the end of the race. Three weeks later Duke brought him back for the Withers at Aqueduct, where he finished 10th. That proved to be Coventry’s last race. His subsequent breeding career was not much, so his big day at Pimlico was his legacy.

Display (19-1), 1926. Display dawdled at the walk-up start, which was delayed by a horse throwing himself over the inside rail. Still, his wide, deep-closing trip with late-blooming jockey Johnny “Sit Still” Maiben turned him into an upset winner. He prevailed by a head in a stretch duel with Blondin. It was a Monday running of the Preakness that was viewed as a prep for the Kentucky Derby five days later, when Display would finish 10th. That was followed by a fourth-place effort in the Belmont. The 1926 Triple Crown season distinguished itself as one of only two times when nine different horses hit the board in the three races (also 2017). According to Equibase, the Fair Play colt who was trained by T.J. Healey won 23 of 103 races and earned $256,326, equivalent to $4.2 million in 2022 money.

Bee Bee Bee (18-1), 1972. During his preparation for the Triple Crown season, the Better Bee colt was transferred to the ownership of the Farish family in Kentucky after his breeder, William Miller, got caught up in a bribery scandal that centered on Chicago mayor Richard Daley and led to the imprisonment of Illinois governor Otto Kerner. After skipping the Derby, trainer Del Carroll decided to stay at Pimlico, where Bee Bee Bee had won by seven lengths in a late-April stakes. Heavy rain made the Preakness look more like a regatta. That was to the detriment of the favorite Riva Ridge, who bookended the Triple Crown with wins in the Derby and Belmont. Eldon Nelson rode Bee Bee Bee in the gate-to-wire victory, his next to last before being retired to stud in Japan.

Oxbow (15-1), 2013. Take your pick of the human highlight. Jockey Gary Stevens at 50? Or Lukas at 77? The old guard came through with an Awesome Again colt who had finished sixth to Orb in the Kentucky Derby. Orb was the odds-on favorite in the Preakness, but this time Oxbow had his way. He enjoyed a loose, early lead, established pedestrian fractions and won by 1 3/4 lengths, leaving Orb fourth in a nine-horse field. It gave Lukas a record sixth Preakness win, a mark broken since by Bob Baffert. Oxbow finished second to Palace Malice in the Belmont, fourth to Verrazano in the Haskell (G1) and never raced again.

Belmont Stakes

Sarava (70-1), 2002. A maiden victory as a 2-year-old and a stakes win on the Preakness undercard were about all Sarava had to lure money from bettors. War Emblem attracted most of the wagers, what with his Kentucky Derby and Preakness victories, but he was a one-geared horse. When he stumbled getting out of the gate, the Belmont suddenly was ripe for an upset. Édgar Prado skillfully tucked Sarava just off the early pace before overtaking Medaglia d’Oro in the stretch to win by a half-length. He really was trainer Kenny McPeek’s “other” Triple Crown contender. Harlan’s Holiday, who had won the Florida Derby (G1) and Blue Grass (G1), was the favorite in the Kentucky Derby. He finished seventh there and then fourth in the Preakness before he was transferred by owner Jack Wolf to trainer Todd Pletcher. McPeek got to drop the mic, though, when Sarava brought home the biggest upset in Belmont Stakes history. The Wild Again colt raced eight more times but never won again before being retired to a breeding career.

Sherluck (65-1), 1961. Carry Back was poised to become the first Triple Crown winner in 13 years. Former President Dwight D. Eisenhower even showed up to see it. Instead, Sherluck happened. Trained by Harold Young, he had lost by a combined 15 lengths to Carry Back in the Derby and Preakness, so dollars bet on him were comparatively few. In the Belmont the Correspondent colt stayed close to the early lead while Carry Back was the target of race-riding tactics by rivals. When jockey John Sellers hit the gas for a trademark close, Carry Back was empty. Later it was found he was running on an injured ankle. Braulio Baeza pressed on with Sherluck and finished 2 1/4 lengths clear of the field. Two more stakes victories would follow before a spotty, international breeding career began in 1962.

Temperence Hill (53-1), 1980. This was the sequel to a controversial Preakness, where Codex’s upset victory over Kentucky Derby-winning filly Genuine Risk was allowed to stand. The Maryland stewards’ unanimous decision to set aside Codex’s ever-widening second turn into Genuine Risk’s path was a bone of contention right through to their rematch three weeks later at Belmont Park. Little did the betting public realize that Temperence Hill, racing for the third time in two weeks, might recapture the form that had won him a slow renewal of the Arkansas Derby (G2). As a $20,000 supplement into the $200,000 race, the Stop the Music colt ridden by Eddie Maple chased soft fractions on the muddy track and wore down Genuine Risk in the stretch for a two-length victory. It was no fluke. Trained by Joe Cantey, Temperence Hill won the Travers (G1) and the Jockey Club Gold Cup (G1) on the way to becoming the champion 3-year-old male of 1980.

Da’ Tara (38-1), 2008. This race was remembered more for who lost than who won. Kentucky Derby and Preakness winner Big Brown was a big bust that hot day when the toilets stopped working for the 94,476 spectators at Belmont Park. To this day the reasons for his being eased in the second turn by Kent Desormeaux are muddled in mystery and rumor. In the meantime, trainer Nick Zito told jockey Alan García to uncork the Tiznow colt and don’t look back. The four-length score was the first gate-to-wire victory in the Belmont since Swale in 1984. Da’ Tara had been only a maiden winner before that. He raced 11 more times but never won again. Last year he was reported to be standing stud in Venezuela.

Birdstone (36-1), 2004. Da’ Tara was not the first Zito spoiler to be overshadowed by an aspiring Triple Crown winner who fell short. Smarty Jones was heavily favored to complete the sweep in 2004, but he and jockey Stewart Elliott got sucked into the blistering duel between Jerry Bailey on Eddington and Alex Solís on Rock Hard Ten. In the last 70 yards, Édgar Prado caught Smarty Jones and got Zito’s Grindstone colt across the finish line with a length to spare. Birdstone was a more modest 9-2 fourth choice that summer when he won the Travers (G1) at Saratoga. After getting hurt at the 2004 Breeders’ Cup, he was retired to stud. Among his progeny was Mine That Bird (see above). Birdstone since has been pensioned to live his later years at Old Friends in Georgetown, Ky.

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