The Preakness Stakes is one of the three legs of the Triple Crown Series. It is dubbed as the "Run for the Black-Eyed Susans". Only 14 horses can compete in the Preakness, and their previous race results determine their eligibility.
The Run for the Black-Eyed Susans has featured the fastest and strongest horses of their generation. That’s why many bet the preakness stakes online along with the other legs in the Triple Crown Series. Unfortunately, at the same time, it has exhibited the most disappointing upsets in its history. In case you’ve missed them, here's the list of the saddest upsets in Preakness Stakes.
Charismatic Vs. Menifee (1999)
Menifee finished second in the Kentucky Derby, barely a neck behind the champion Charismatic. But, he had a lot of support in the 1999 Preakness Stakes, where he was sent out as the morning line favorite at 2–1 in a field of 13 colts and one filly.
Charismatic won by one and a half lengths beating Menifee, who finished second. The race was completed in 1:55.32 on a fast track. Cat Thief and Vicar claimed the lead early in the race, while Menifee fell into mid-pack at eighth and Charismatic trailed in tenth. Charismatic won by 1 1/2 lengths after making a move on the outside around the second turn. Menifee finished second in the Preakness Stakes.
On the betting odds, Charismatic was the fourth option. However, the race outcome has proved that the window favorites aren't always favored in the track. Charismatic defeated Menifee two consecutive times.
Red Bullet Vs. Fusaichi Pegasus (2000)
In Preakness 2000, Red Bullet, ridden by Jerry Bailey, won by three and three-quarter lengths over Fusaichi Pegasus, who finished second. Fusaichi Pegasus won in 2:01.12 for the 1 14 mile race in Kentucky.
Red Bullet was listed at Pimlico Race Course as the second choice in the 1 3/16 miles classic in Pimlico. Red Bullet, who started from the fourth position, had a slow start in the race. Having passed the stands in seventh place 6 1/2 lengths behind in the field of eight, jockey Jerry Bailey restrained his horse. Red Bullet took an unfortunate stride into the clubhouse turn. He made his way forward and passed Impeachment and Captain Steve on the backstretch.
Fusaichi Pegasus and High Yield were in front when Red Bullet entered the far turn and succeeded in overtaking each of them. Then, with each stride, he started to ace ahead of the Kentucky Derby champion.
Fusaichi Pegasus skipped the Belmont Stakes after his loss in the Preakness.
Bernardini Vs. Barbaro (2006)
The Kentucky Derby 2006 was won by Barbaro. He went on to compete in the Preakness Stakes at odds of 1-2. The Kentucky Derby hero then faltered and slid behind the storming field before being yanked in frustration by jockey Edgar Prado in the first 200 yards of the race to the first turn.
Barbaro, the 1-2 favorite in a field of nine, crashed through the starting gate moments before the race was scheduled to begin. He was driven back into the gate, and the second try went off without a hitch. But, with the horse limping in distress, jockey Edgar Prado pulled Barbaro midway along the front stretch of the 1 3/16-mile race.
On January 29, 2007, Barbaro was euthanized after his vets concluded that he could not be saved.
Bernardini, a 12-1 underdog, won by 5 1/4 lengths in 1:54.65 over the 1 3/16 mile course at Pimlico. Unfortunately, Bernardini didn't participate in the Belmont Stakes. It's the fourth time in 60 years that neither the Kentucky Derby winner nor the Preakness heroes were in the race.
Shackleford Vs. Animal Kingdom (2011)
Animal Kingdom, the Kentucky Derby winner, finished second in the Preakness Stakes in 2011. The Kentucky Derby hero, favored at 2-1, recovered from last to second in the field of 14 horses, finishing second in 1:56.47 as the winner completed the 1 3/16-mile race in 1:56.47.
Shackleford fought for the lead in the Preakness from the start. He followed Flashpoint at first, then took the lead and wouldn't give it up, despite a strong surge by Animal Kingdom.
Oxbow Vs. Orb (2013)
Orb arrived as the Kentucky Derby favorite in 2013. Orb had become the center of attention ever since he won the Kentucky Derby.
Kentucky Derby champion Orb started the first period in the center of the pack behind leader Oxbow, then moved to the outside and began making a run before being caught back in the pack and finished fourth.
Oxbow led from the start of the 1-3/16 mile race and became the first wire-to-wire champion since 1982. Additionally, he was the third horse to collect $1 million in purse money after finishing second at Belmont Stakes. The National Thoroughbred Racing Association (NTRA) recognized him as the top three-year-old racehorse in the United States.
Final Thoughts
The Preakness Stakes is a prestigious race that jockeys and thoroughbreds aspire to win at least once in their careers. While this race has showcased the strongest heroes, it has also featured some of the most dramatic upsets fans will never forget.
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