The biggest upsets in Belmont Stakes history

As Alicia Keys told us back in the day, there’s nothing you can’t do in New York.

It’s the concrete jungle, where dreams are made. And those sentiments couldn’t be more true for the runners and riders dreaming of winning the Belmont Stakes (G1) in Elmont, New York. The "Test of the Champion" is the final stop on the Triple Crown journey, but it’s as well known for its shocks as its superstars.

Here are the five biggest upsets in Belmont Stakes history.

5. Commendable (2000)

Trainer D. Wayne Lukas is no stranger to shocking outsider victories, but arguably none are as famous as Commendable’s win in the Belmont.

Aptitude was the 9-5 favorite, after he finished second in the Kentucky Derby (G1), but Commendable was on hand to shock the world.

He won just one of his seven races as a two-year-old, but Lukas had Commendable tipped as a Triple Crown contender. He lost another four races leading up to the Triple Crown series, though, and finished 17th in the Derby.

Commendable was unsurprisingly one of the outsiders for the Belmont but raced prominently under a positive ride from Pat Day. He took the lead a half-mile from the line and stayed on to hold off Aptitude by 1 1/2 lengths.

Commendable paid $39.60 for a $2 win wager.

4. Ruler on Ice (2011)

All the talk in 2011 was the battle between Kentucky Derby winner Animal Kingdom and Shackleford, who put an end to the Triple Crown dream in the Preakness (G1). The two met again in the Belmont, and all eyes were on the leading duo at the top of the market.

Ruler On Ice had never won a stakes race and didn’t run in the Derby or Preakness. That left him as a 24-1 outsider, but jockey Jose Valdivia Jr. put Ruler on Ice right off Shackleford, and the longshot seemed to relish the sloppy conditions.

Animal Kingdom stumbled out of the gate and couldn’t get involved, while Shackleford tried to go hoof-to-hoof with Ruler on Ice but fell away back to fifth.

He splashed through the tough conditions to hit the line in front and paid a whopping $51.50 for the win.

3. Da’ Tara (2008)

You could look at the form of the nine horses in the 2008 Belmont after the fact and still struggle to pick out the winner. That was how hard it was to imagine Nick Zito’s horse winning, considering he had only won a maiden race.

Da’ Tara was the largest price, at 38-1, with all the attention on 1-4 favorite Big Brown, who won the Derby by almost five lengths and then destroyed the Preakness competition.

It all went wrong for Big Brown in the Belmont, though, and jockey Kent Desormeaux bore the brunt of the blame for a ride that saw him nearly run up the heels of Da’ Tara and then bump into Tale of Ekati. Big Brown was eased on the final turn and became the first Triple Crown hopeful not to finish the Belmont.

Meanwhile, Da’ Tara was loose on the lead, and nobody could get close to him, as he stole away from the field to win by more than five lengths and pay $79 to lucky bettors.

2. Sarava (2002)

Bob Baffert’s War Emblem was another Triple Crown hopeful going into the Belmont, after he pulled off a 25-1 upset in the Kentucky Derby and won the Preakness with another frontrunning performance.

His Triple Crown dream ended at the gate in the Belmont, however, as War Emblem stumbled at the start and ended up on his knees. He recovered and made up ground but met more trouble during the race, and even though he took the lead at the final turn, he started to fade quickly.

Medaglia d’Oro, who finished fourth in the Derby and eighth in the Preakness, took up the lead, but he was run down by Sarava in the stretch.

Sarava was the highest-priced longshot in Belmont history. He paid out a staggering $142.50 for the win.

1. Birdstone (2004)

While Sarava had the longest odds, he may not have provided the biggest shock in Belmont history.

In 2004, a record crowd of 120,000 went to Belmont Park to see Smarty Jones, a horse who had won the Derby by 2 3/4 lengths and then the Preakness by 11 1/2.

“Smarty Fever” was at an all-time high, and the public was hugely invested in him, as the colt’s owners received thousands of good-luck letters. When Smarty Jones arrived from Pennsylvania for the race, he was escorted to Belmont by two police motorcycles and three helicopters, while other police cars blocked off intersections.

But it did not go to plan for Smarty Jones, who started well but was quickly pressured by Rock Hard Ten and Eddington. The battle for the lead quickened the pace, and the first 1 1/4 miles took just 2:00.52 — a time that would’ve won all but four editions of the Kentucky Derby.

As Smarty Jones tired, Birdstone came flying, and he crossed the line in front to a stunned silence. It was such a surprise the owners apologized to the crowd in the winner’s circle. Birdstone paid out $74 for the win.

"We came to see a coronation. Instead, we got a sporting event," said John Hendrickson, the husband of Birdstone's owner, Marylou Whitney.