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Triple Crown Near-Misses: 10 Disappointing Endings

Triple Crown Near-Misses: 10 Disappointing Endings

For every horse who has won the Triple Crown, four horses have come close but missed winning one of the three races. We've had 52 near-misses, some so agonizing that it tears at our very souls to watch replays. Some horses were within inches of winning; others fell upon bad luck and lost. Here are 10 of the most excruciating near-misses:

Twenty Grand (1931) was the favorite to win the Preakness Stakes among such notables as Equipoise and Mate, but was bumped hard by Soll Gills on the clubhouse turn, losing several strides. He fought back and tried to make his move in the stretch, but jockey Charlie Kurtsinger had to check him sharply because Surf Board blocked his path. He finally got around Surf Board but finished 1 1/2 lengths behind Mate. He got revenge in the Kentucky Derby and Belmont, setting a track record and stakes record and winning by four lengths and 10 lengths, respectively.

Native Dancer (1953) the "Gray Ghost of Sagamore" and favorite of many television watchers, entered the Kentucky Derby as the undefeated odds-on-favorite. But he, too, was bumped by Money Broker in the clubhouse turn and lost valuable ground, at one point lagging 10 lengths behind. He slowly made up the deficit and made his trademark stretch run, but it was too late as 25-1 longshot Dark Star held on to win by a head. Native Dancer would go on to win his next 10 races, including the Preakness and Belmont, to go 21-for-22 in his remarkable career.

[Video: Native Dancer's Kentucky Derby loss]

Tim Tam (1958) wasn't the favorite going into the Derby because the crowd favorite, the come-from-behind Silky Sullivan, was also running. But the winner of the Fountain of Youth and Florida Derby won by 1/2 length over Lincoln Road. He lengthened that victory to 1 1/2 lengths over the same horse in the Preakness, and in the Belmont, was within a head of the lead at the quarter pole. But he broke a sesamoid bone in his right foreleg and finished 6 lengths behind Cavan, still managing second place. He was retired the next day.

Majestic Prince (1969) was the heir apparent to Citation, and many expected him to win the Triple Crown. The undefeated colt met expectations at first, winning the Derby by a neck and the Preakness by a head. Trainer Johnny Longden knew he had a tired colt and wanted to skip the Belmont. He also was nursing a sore tendon. But Longden succumbed to pressure by Majestic Prince's owner and entered him in the Belmont. The horse was never a factor, finishing second by 5 1/2 lengths to Arts and Letters. It was his last race.

Canonero II (1971) was on no one's Derby radar when he was shipped in from Venezuela and named part of the pari-mutuel field. But he shocked everyone by coming from 20 lengths off the lead to win the Derby by a neck over Eastern Fleet. Many horse racing experts said the win was a fluke, but the $1,200 yearling purchase shut up naysayers with a 1 1/2 length victory in the Preakness. But Canonero II was nursing a hoof infection, and in front of thousands of members of the Latino community cheering him on in the Belmont Stakes, the Cinderella story ended. He struggled to finish fourth.

Spectacular Bid (1979) rode a 10-race win streak into the Kentucky Derby, and won going away. He won the Preakness by 5 lengths and was ready to become the third Triple Crown winner in a row. But on the morning of the Belmont Stakes, he stepped on a safety pin, causing a bruise in his left front hoof. He didn’t change leads during the entire race and, forced into a swift pace by jockey Ron Franklin, tired in the long Belmont homestretch and finished third. It took him three months to recuperate, but he bounced back with an undefeated 4-year-old season to finish with 26 wins in 30 races.

[Video: Spectacular Bid finished third in the Belmont Stakes]

Silver Charm (1997) tipped his hat to bettors with meteoric workouts before the Derby and was made the 3-1 second choice. He did not disappoint, fighting off the favorite, Captain Bodgit, by a head. The Bob Baffert-trained horse replayed the exciting finish in the Preakness, exchanging leads with Free House several times before Silver Charm eked a nose in front at the wire in a photo finish. In the Belmont, Silver Charm and Free House battled it out in the stretch again, but this time Touch Gold, who had led earlier, found another gear and passed them both, beating Silver Charm by 3/4 of a length.

Real Quiet (1998), nicknamed "The Fish" by trainer Bob Baffert because of his thin appearance when viewed head-on, was only an 8-1 shot to win the Derby. He started slowly and was eight lengths behind at one point, but took the lead heading into the homestretch, fighting off a fast-closing Victory Gallop by 1/2 a length. They reenacted their stretch run in the Preakness, but this time Real Quiet pulled away from Victory Gallop, winning by 2 1/4 lengths. But Victory Gallop exacted revenge in the Belmont. With Real Quiet taking a four-length lead in the homestretch with a Triple Crown in his grasp, Victory Gallop made his move on the tiring horse. It was a photo finish at the wire, with Victory Gallop winning by less than a nose.

[Video: Real Quiet loses the Triple Crown by a nose]

Charismatic (1999) sought to end the 21-year Triple Crown rout, but he had an uphill battle. A former claiming horse, he won only one of 7 starts as a 2-year-old. He won the Lexington Stakes, which got him into the Derby, and he did not disappoint. Starting as a 31-1 longshot, he overtook Cat Thief in the stretch and withstood a charge from Menifee to win the Derby. Charismatic copied his Derby win in the Preakness, stalking the leaders and then taking the lead four wide on the far turn. He again fighting off Menifee for a 1 1/2-length victory. But like Tim Tam, after grabbing the lead in the stretch of the Belmont, Charismatic fractured his left front leg in two places, allowing Lemon Drop Kid to get the victory. Charismatic, living up to his name, finished third. He never raced again but won Horse of the Year for his efforts.

Smarty Jones (2004) was a crowd favorite. He was bred in Pennsylvania and survived a fractured skull in a gate accident as a 2-year-old. The undefeated colt won the Derby by 2 3/4 lengths, giving trainer John Servis and jockey Stewart Elliott wins in their first Derby starts. He dominated the Preakness, winning by a record 11 1/2 lengths. But in the Belmont, Smarty Jones set too fast of a pace at the beginning and ran out of steam. Holding a 3 1/2-length lead at the quarter pole, he couldn't withstand a charge from Birdstone, who passed him en route to one-length victory. He never raced again.

[Video: Birdstone beats Smarty Jones in the Belmont Stakes]


Peter Lee is the author of Spectacular Bid: The Last Superhorse of the Twentieth Century, which is on sale now in bookstores. A former journalist, he is a contributing writer to Past the Wire and maintains The Way to Churchill Downs, a blog that covers Kentucky Derby prep races for 2- and 3-year-olds.

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For me, it was California Chrome in 2014, because I was there, AND it was my Birthday. I thought for sure it had to happen. And as the 4/5 fav, I think everyone thought it was going to happen. That may have been the all time great disappointment in TC history.

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