Ranking the Most Disappointing Triple Crown Misses in History

Brendan O'Meara@@BrendanOMearaFeatured ColumnistJune 2, 2014

Ranking the Most Disappointing Triple Crown Misses in History

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    Anonymous/Associated Press

    Eleven horses in racing history have won the Triple Crown. Since Affirmed became the most recent Triple Crown winner in 1978, 11* horses have won the Kentucky Derby and Preakness before losing in the Belmont Stakes.

    The anticipation every yearfrom Spectacular Bid in 1979 to California Chrome this yearis part, if not most, of the excitement. 

    Which of the 11 Triple Crown near-misses was the most disappointing? Based on the context at the time of the Belmonts, how easily the horses won their Derbies and Preaknesses and how their Belmont unfolded, let's take a deeper dive into 35 years of heartbreak.


    *I'll Have Another is not included on this list since he did not run in the Belmont.

11. California Chrome, 2014

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    Kathy Willens/Associated Press

    The Triple Chrome run ended not by a nose and not by a pole; he simply got beat by fresher horses.

    It's a disappointing finish because everything lined up for him so well and he still couldn't win the Belmont. We still haven't seen in a Triple Crown winner in 36 years.

    The weather was perfect. He never had a nagging injury that derailed his training. All signs were pointing to a stellar effort and you know what? He still ran well, it just wasn't what everyone had come to expect. That's where the disappointment lies.

    Victor Espinoza, Chrome's jockey, said afterward in a NYRA press release*.

    A little tired. I thought he was...turning for home I was just waiting to have the same kick like he always had before, and today he was a little bit flat down the lane. [Taking dirt didn't both him] at all. I was nice and comfortable in there, and I had a chance to move out, and when I moved out he just don't have that today. I think it was tough for him. He ran back-to-back races in different tracks - and all those fresh horses. But he feels good.

    *: Quote issued from a press release.

10. Silver Charm, 1997

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    Silver Charm's Triple Crown run was as thrilling as they come. There was no disappointment in the purest sense because he generated excitement with every stride.

    In the final stretch of the race, he eventually ceded the lead to Touch Gold, his rival through three legs of the Triple Crown. It was only disappointing in that Silver Charm couldn't ultimately close the deal.

    For trainer Bob Baffert, he couldn't possibly know how close he'd come just a year later. In two years, he lost two Triple Crowns by less than a length combined.

    But that's only a warm-up compared to the other doozies on this list.

9. Alysheba, 1987

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    This might be the worst calling of the Belmont Stakes ever, which makes this race disappointing enough. When added to Alysheba being completely dusted down the lane, it makes for a depressing renewal of the Belmont.

    Alysheba clipped heels with Bet Twice and nearly fell in the Derby, but recovered well and eventually drove by Bet Twice to win. The Preakness saw another duel between Bet Twice and Alysheba, with the latter getting the best of his rival in the final strides.

    It made for a great re-rematch at Belmont, only to see Bet Twice demolish Alysheba.

    The racecaller threw boring salt into a disappointing wound. He said, "Gone West won't win this one." What?

    There was a horse going for the Triple Crown and you don't even call out the horse who lost the Triple Crown? Inexcusable. 

8. War Emblem, 2002

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    War Emblem's tale has been discussed ad nauseam as of late because of his jockey, Victor Espinoza, who rides California Chrome and is that rare jockey who has multiple cracks at the Triple Crown. The most recent such rider was Kent Desormeaux in 2008. 

    War Emblem needed the lead. That's how he won the Derby and the Preakness. He broke from Post 10 in the Belmont and didn't break sharply. He was off toward the back of the pack and didn't reach the lead until late in the race. By that point, it was all over. He was gassed. 

    Medaglia d'Oro and Sarava swallowed War Emblem at the top of the stretch. He faded and finished far back of the leaders. It was a disappointing effort that never materialized into anything greater than a wet sneeze.

7. Funny Cide, 2003

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    Funny Cide was a scrappy New York-bred gelding owned by a bunch of guys who showed up to Churchill Downs for the Derby in a school bus. In a lot of ways, they're like the DAP owners of California Chrome. Sackatoga Stables was fun to watch as their gelding came home to New York for his attempt to be the 12th Triple Crown winner in history.

    Then it rained and turned the track into muck. Funny Cide never took to the track and was eventually overcome by his rival, Empire Maker. 

    Jose Santos, Funny Cide's jockey, told reporters afterward:

    I am very proud for all the New Yorkers, Spanish people and New York-bred people who came out to support this horse today. I am so thankful for everybody’s support. I am not disappointed. The track affected him, he didn’t handle it good. I still think I have the best 3-year-old. We will be back. I can’t wait for Funny Cide and Empire Maker to meet again, it will be a great rematch.

    Trainer Barclay Tagg added:

    I feel bad for all the people who came out. We had a good first quarter, 48 then 1:13 and change (for the half) was a sensible pace. I don’t know if it was the extra 1/4 mile. He looks all right. We were beaten by a good horse. I don’t know what else to say. I am being honest. It is horse racing.

    Funny Cide ran for a few more years and was always a draw no matter where he went.

6. Big Brown, 2008

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    The 2008 Belmont Stakes, otherwise knows as the "Karma Stakes," had Big Brown entering as the best horse of his generation by far. He won the Kentucky Derby breaking from Post 20. He won the Preakness in a gallop. 

    Then Rick Dutrow, the much-maligned trainer, said the Triple Crown was a "foregone conclusion." Dutrow said during a conference call in the lead up to the 2008 Belmont, per The Associated Press (via ESPN):

    I feel that he will do it. I feel like it's actually a foregone conclusion. To me, I just see the horses he's in with and I see our horse so I expect him to win this race.


    I know that when that day actually does come, and if our horse is in good shape, it will be the most exciting, thrilling moment of my life. So I just ... I know that that's coming, but right now I'm just staying involved with our horse and what we think is best to get him there the right way and it keeps us plenty busy.

    Caught up in this mess was the horse. Big Brown was always hampered by foot problems. He suffered from quarter cracks (a crack to the quarter section of the hoof, not a crack a quarter-inch long). His best surface may have been grass, too. In some ways, Big Brown could have been a modern-day Secretariat, a horse who was also a monster on grass. 

    In the Belmont on that swelteringly humid day, Big Brown was ultimately eased at the top of the stretch and galloped home last of them all. 

    Big Brown was never quite as dominant again. He later won the Haskell in a drive and beat a very formidable field of older horses on grass, but the Belmont will always be a blight for his trainer, and for the controversial ownership group IEAH.

    No matter how you slice it, Big Brown's Triple Crown run was a huge disappointment. Big Brown's jockey Kent Desormeaux had felt this before, but you'll have to wait a few more slides.

5. Sunday Silence, 1989

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    Easy Goer and Sunday Silence were the modern-day Affirmed and Alydar. The two horses wrestled throughout the 1989 Triple Crown with Sunday Silence besting Easy Goer in the Derby and Preakness.

    At the Belmont, however, it wasn't even close.

    Turning for home, Easy Goer left Sunday Silence in the dust. Thus he didn't become like his sire Alydar, who never could eclipse his rival. Shug McGaughey, Easy Goer's trainer, told The New York Times' Steven Crist

    I knew he could run a race like this. I told my assistant walking over here, 'If this goes the way I think, it will be fun to watch.' The Preakness was the first time he had to fight and I think it's clear that did him some good.

    I had confidence that he could beat Sunday Silence. I never questioned his ability, or anything I did with him.

    Sunday Silence couldn't keep it close and failed to become the 12th Triple Crown winner, thwarted at the hands (errr...hooves) of his pesky rival.

4. Charismatic, 1999

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    Charismatic, like all the other failed Triple Crown winners, captivated the country. As engaging as the horse was, his jockey was every bit the story. Chris Antley was making a comeback after battling addiction and manic depression. 

    Charismatic's run through the Triple Crown nearly saved Antley, but when Charismatic broke down after the wire (a non-fatal leg fracture), it appeared to break Antley beyond repair.

    Joe Drape of The New York Times wrote: 

    These virtues merged on national television on the afternoon of June 5, 1999, at the finish of the Belmont Stakes, when Antley leapt off the back of an overachieving colt named Charismatic, who had fractured a leg in the stretch. With tears streaking his dusty face, Antley lifted the colt's left leg in his hand until an ambulance arrived. Before the Belmont, Antley and Charismatic had captured the Kentucky Derby and the Preakness Stakes, giving the public a made-for-television tale of a second-rate horse and an umpteenth-chance jockey stalking a Triple Crown.

    They finished third that day, though Antley's quick reaction was hailed for saving Charismatic's life. But as he had done previously in his tumultuous riding career, Antley followed this storybook moment with a blank chapter, a familiar one in which talent gave way to torment.

    Charismatic had overachieved and so too had Antley by that point. His spiral into depression and madness finally claimed his life, and the 1999 Triple Crown run is inextricably tied to Antley's downfall.

3. Smarty Jones, 2004

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    Smarty Jones was never supposed to get the distance. He wasn't supposed to get the Derby distance, or the Preakness distance, let alone the Belmont distance. He was sired by a world-record miler in Elusive Quality. His dam, I'll Get Along, was sired by Smile, a sprinter. Smarty Jones wasn't meant to do what he nearly did.


    He won the Derby in impressive fashion, then won the Preakness by a record 11 1/2 lengths. The Belmont Stakes was going to be the apotheosis of Smarty Jones and the "Smarty Party."

    Smarty Jones was the horse to beat, so horses were going to come after him. That much is expected in sport. What isn't expected is a flurry of attacks from several horses meant to tire Smarty to the detriment of their own races.

    Pat Forde, then of ESPN, wrote in 2008 (the year Big Brown was vying for the Triple Crown):

    But a gang-up scenario is hardly unimaginable. Some people believe it's happened many times before in this unforgiving sport, including in this very race.

    Roy Chapman, owner of the last horse to arrive in New York with a shot to win the Triple Crown, Smarty Jones, went to his grave in 2006 convinced that Smarty's '04 Belmont defeat was a setup. He believed elite jockeys Jerry Bailey and Alex Solis engaged in suicidal tactics designed to make the big horse fail.

    "I never saw two riders ride so hard to lose a race in my life," Chapman growled one week after his colt lost the Crown deep in the stretch to Birdstone. "They just were out for one thing: making sure Smarty didn't win." 

    Purge, Rock Hard Ten and Eddington all took aim at Smarty Jones. Eddington, ridden by Jerry Bailey, dropped back and then surged back up into contention. In conversations I've had with Bailey (who, in his own words, still gets "so much s--t" about his ride), he said he was supposed to bring Eddington to eyeball Smarty. It was their only chance at winning; otherwise, Smarty would've galloped off to the Triple Crown.

    It didn't look that innocent on camera. It's amazing Smarty held on as long as he did. He lost by just a length. If the race were run under "normal" competitive conditions, he would've probably won. 

    Nobody was more disappointed than the record 120,139 people on hand. 

2. Real Quiet, 1998

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    This is racecaller Tom Durkin at his finest. Just listen to the call during the final furlong. 

    Victory Gallop clipped Real Quiet at the wire and snatched the Triple Crown away by a nose. Victory Gallop went blow-for-blow with Real Quiet in every leg of the Triple Crown. In the Derby, he came roaring at a "leg-weary" Real Quiet. Victory Gallop again ran hard at Real Quiet in the Preakness. It was only fitting that Victory Gallop would be the one to steal it away from him and jockey Kent Desormeaux.

    At the time of Real Quiet's loss, there was a $5 million bonus for any horse who won the Triple Crown. About the length of a coffee cup was the difference between a second-place check and $5 million smackers. 

    "Being beat at the finish line, it hurts a lot," Desormeaux told The New York Times' Joseph Durso. "Nearing the finish line, I could taste it, and I even felt it for a moment."

    That's the very illustration of disappointment.

1. Spectacular Bid, 1979

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    Spectacular Bid may have been the most dominating horse to sweep the Derby and Preakness then fail to win the Belmont.

    Three horses had already won the Triple Crown in the 1970s. Secretariat snapped a 24-year Triple Crown drought in 1973. Seattle Slew won it in 1977 and Affirmed in 1978. Spectacular Bid was primed to make it a Triple Crown triple to close out the Disco Era.

    The Bid swallowed the field in the Derby. He crushed a small field in the Preakness. The Belmont was his.

    Then the Bid was undid by a safety pin. A pin came loose from his bandages and he stepped on it. It punctured his hoof and left him sore. As a result, he ran a flat Belmont Stakes and finished third.

    Spectacular Bid lost his Belmont in a time when people had come to expect it as something as a matter of routine. Triple Crowns are easy! The Bid's failed attempt was just the first in a long line of disappointments. He's the prequel for today's drought.

    He started the Triple Crown losing streak, setting the tone of disappointment that has seen six American presidents and several versions of Arnold Schwarzenegger.

    The big question is this: Will California Chrome snap this streak, or will he just be the next in a long line of disappointments?