Whether you are a horse racing enthusiast or not, most are aware of what is known as the Triple Crown. For those of you who don’t, it’s a 3-race event for three-year-old thoroughbreds. It consists of the Kentucky Derby, Preakness Stakes, and Belmont Stakes. It all starts with the Derby, which is run on the first Saturday in May. Then comes the Preakness on the third Saturday in May and the Belmont three weeks later (ends up being first or second Saturday in June).

Winning one of the three legs is considered quite an accomplishment. However, the goal is of course to win all three events. A horse that is able to do so, is said to have won the Triple Crown.

The Kentucky Derby was the last to be inaugurated way back in 1875. It wasn’t until 1919 that a horse (Sir Barton) was able to win all three races. It wasn’t until 11 years later (1930) that another 3-year-old thoroughbred (Gallant Fox) was able to do it again. Six more horses would conquer the feat by 1948.

There was then a 25-year gap until the great Secretariat etched his name into the history books. Seattle Slew (1977) and Affirmed (1978) shortly followed and remains the only time that it’s been done in consecutive years.

Affirmed became quite a popular horse in the leading decades, as the search for the next winner continued on for quite some time. Some even wondered if there would ever be another horse that won all three legs. That was put to rest in 2015 when American Pharoah snapped the 37-year drought.

During the long break between Affirmed and American Pharoah, there were quite a few heartbreaking moments when horses that had won the first two legs, failed to deliver at the Belmont. I’ve recapped a number of those below. In total there have been 35 horses who went into the final leg with a chance to make history. Of those contenders, 23 of them for one reason or another came up short.

Recent Contenders That Failed to Win Horse Racing’s Triple Crown

California Chrome (2014)

Many believed that this was going to be the horse that snapped the drought. California Chrome put on a dominating performance at the Kentucky Derby and backed it up with another great showing at the Preakness. Unfortunately, California Chrome was stepped on by another horse out of the gate. Despite the setback, he still managed to finish 4th. After the race, it was later found out that he actually tore some tissue in his right front heel. California Chrome has since gone on to become the all-time leader in earnings won for North American horse racing.

I’ll Have Another (2012)

I’ll Have Another became the third to be scratched prior to the race.  Sighting a slow-healing tendon injury, trainer Doug O’Neill and owner J. Paul Reddam announced I’ll Have Another’s retirement from racing the Friday before the 2012 Belmont.

Big Brown (2008)

Big Brown was a monster 3-10 favorite heading into the 2008 Belmont.  He started the race well, running in third place just behind eventual winner Da’Tara, but was pushed outside and fell back awkwardly before jockey Kent Desormeaux pulled the horse up in the homestretch, later saying that something was wrong.  Big Brown is the only Triple Crown hopeful to date that did not finish the leg and, while no physical ailment was ever found to explain the poor performance, there is evidence to suggest that his right hind shoe was dislodged and may have caused the incident.

Smarty Jones (2004)

In 2004, we all thought Smarty Jones was going to get it done. The funny thing is that his run is strikingly similar to that of Big Brown. Like Big Brown, he was the undefeated Derby favorite. He then, like Big Brown, went on to dominate the first two legs. At the Belmont, Smarty Jones had the lead in the stretch but could not hold off a late charge from 36-1 longshot Birdstone and had to settle for second. Hopefully, Big Brown won’t share the same fate.

Funny Cide (2003)

The next year Funny Cide raced his way to stardom by upsetting the favored Empire Maker in the Derby. He then dominated the Preakness by nine lengths. But Empire Maker had sat out the Preakness to rest and came back at the Belmont to end Funny Cide’s bid.

War Emblem (2002)

War Emblem was our first real challenger of the new millennium. This horse was giving Bob Baffert yet another shot at the title. It wasn’t even close in the Belmont however as he stumbled right out of the gate. His eighth place finish is the worst ever by a horse vying for the the ultimate price for 3-year-olds.

Charismatic (1999)

Charismatic was a 31-1 longshot in the Kentucky Derby but when on to win that race by a neck and took the Preakness Stakes by a couple lengths. He, like the two horses before him, looked good in the home stretch of the Belmont, but he ended up third. He also tragically broke two bones in his leg in that stretch run.

Real Quiet (1998)

A year later, Real Quiet was making plenty of noise as Baffert had himself another quality horse. If Baffert couldn’t stomach Silver Charm’s heartbreaking loss in the Belmont, this one surely stopped him, heart. Real Quiet led by four lengths with less than a quarter mile left in the Belmont, but out of nowhere came Victory Gallop to win by a nose.

Silver Charm (1997)

Silver Charm looked the part of a champion. This super horse was one of Bob Baffert’s best, but he just wasn’t quite good enough. He was in the lead down the home stretch of the Belmont, but Touch Gold overtook him to win by less than a length.

Sunday Silence (1989)

Affirmed and Alydar were the story in 1978 and Sunday Silence and Easy Goer were the talk of thoroughbread racing in 1989. Sunday Silence won the Derby over the favored Easy Goer and then edged him out again at the Preakness by a nostril. Easy Goer would have his revenge winning by eight lengths.

Alysheba (1987)

Alysheba won the Derby despite stumbling down the stretch. Many were skeptical before the Triple Crown got underway as he’d had surgery just a couple months prior to fix a breathing problem. After he overcame all that, he seemed unstoppable until he ran fourth. The race was won by 14 lengths by Bet Twice.

Pleasant Colony (1981)

Two years later Pleasant Colony had us hoping again. This horse was very tall, so much so that it looked uncoordinated. After a fifth-place finish in the Florida Derby his trainer was fired and the rest was history – well, almost. He took the Derby and the Preakness and also finished third at the Belmont.

Spectacular Bid (1979)

Seattle Slew won the Triple Crown in 1977 and Affirmed won in the next year. After Spectacular Bid took care of business in the Derby and the Preakness, it looked like the Triple Crown was getting to be too easy. Spectacular Bid didn’t have the same powerful kick that he had in the first two legs and wound up third. Rumor has it that he stepped on a safety pin the day before the big race, which caused him a lot of discomfort.

Triple Crown History: Results of Horses Who Had a Chance to Win

YearHorsePerformance at Belmont
1919Sir Barton1st
1930Gallant Fox1st
1932Burgoo KingSCRATCH
1935Omaha1st
1936Bold VentureSCRATCH
1937War Admiral1st
1941Whirlaway1st
1943Count Fleet1st
1944Pensive2nd
1946Assault1st
1948Citation1st
1958Tim Tam2nd
1961Carry Back7th
1964Northern Dancer3rd
1966Kauai King4th
1968Forward Pass2nd
1969Majestic Prince2nd
1971Canonero II4th
1973Secretariat1st
1977Seattle Slew1st
1978Affirmed1st
1979Spectacular Bid3rd
1981Pleasant Colony3rd
1987Alysheba4th
1989Sunday Silence2nd
1997Silver Charm2nd
1998Real Quiet2nd
1999Charismatic3rd
2002War Emblem8th
2003Funny Cide3rd
2004Smarty Jones2nd
2008Big BrownDNF
2012I’ll Have AnotherSCRATCH
2014California Chrome4th
2015American Pharoah1st