Here Are The Biggest Preakness Long-Shot Winners … Ever

Written By Darren Cooper on May 19, 2022

Long shot fever has taken hold of the horse racing world.

After winning the Kentucky Derby at 80-1 odds, Rich Strike became the second-longest, or rather most improbable, long shot to ever achieve this feat.

The horse named Rich Strike will not be participating in the Preakness Stakes event taking place in Baltimore on Saturday. This race, being the second in the Triple Crown series, includes a field of nine horses, comprising both favorites like Epicenter and longshots like Happy Jack, providing betting options for spectators.

For convenient Preakness betting in Virginia, the TVG app is your best choice. This app is exclusively designed to cater to horse betting enthusiasts. Simply click the link below to explore exclusive offers for the upcoming premier racing event.

The Preakness has never witnessed a victory by a horse with odds of 80-1. Here, however, are the six most remarkable underdogs to triumph in the prestigious race held in Baltimore.

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1975: Master Derby, 23-1

This is a tale where Foolish Pleasure emerged victorious in the Kentucky Derby, leaving everyone with the assumption that he would undoubtedly secure the Triple Crown.

It happens every year.

Despite Foolish Pleasure garnering most of the public’s attention, Master Derby went relatively unnoticed, despite his strong performance at Churchill Downs, where he finished fourth. Additionally, he had achieved victories in both the Louisiana Derby and Blue Grass Stakes.

During the initial half of the race, Master Derby maintained its position in third place along the rail. As the race progressed, Master Derby caught up to a group of four horses who were leading the pack. In the final stretch, Foolish Pleasure closely trailed Master Derby, but Master Derby was aware of his presence and managed to cross the finish line with a one-length advantage.

Master Derby, who lived for 27 years, holds the record for the highest odds to win the Preakness.

1925: Coventry, 21-1

A century ago, there was significant skepticism surrounding Coventry due to his training under William Duke, a Frenchman. Many believed that the American style was far superior and doubted if Coventry could measure up.

Coventry suffered a major defeat at the Wood Stakes the previous weekend, with the race being described by The Daily Racing Form as highly dramatic. The blame for the outrageous initial speed was placed on the lead horses, specifically Backbone.

Coventry seized the opportunity to race effortlessly, securing a four-length victory while his competitors gradually lost steam. Remarkably, this triumph stood as his sole win out of the five races he participated in. Unfortunately, Coventry’s luck took a turn in his subsequent race at Aqueduct, as he suffered a breakdown that led to his retirement and transition into a stud.

1926: Display 19-1

Display, the lesser-known sibling of the legendary Man o’ War, enjoyed a prosperous racing journey that spanned until he reached the age of six.

The Preakness race began with an intense commotion. Canter refused to enter his starting position and proceeded to kick Navigator. Meanwhile, Mara, another horse, unexpectedly reared and found itself trapped against a temporary inside rail.

Canter, Rock Man, and Dress Parade quickly surged ahead when the race commenced. However, their initial burst of energy seemed to have drained them, resulting in a gradual decline. As a result, the competition transformed into an enduring struggle between Display and Blondin.

Display remained tireless and successfully fended off Blondin to secure victory in the Preakness. As a four and five-year-old, Display continued to triumph in numerous subsequent races.

1972: Bee Bee Bee 19-1

In 1972, Riva Ridge emerged as the shining star among horses, triumphantly claiming victory at the prestigious Kentucky Derby. As is commonly observed, expectations were high for Riva Ridge to continue his winning streak and effortlessly secure a win at the upcoming Preakness.

Bee Bee Bee, hailing from Maryland, had emerged victorious in two smaller races held at Pimlico. Being his home turf, he was well acquainted with the track. However, when rain poured down and made the track muddy, Riva Ridge hesitated.

Bee Bee Bee, a truly exceptional mudder, achieved a remarkable victory by almost two lengths, making it one of the most surprising upsets in Preakness history.

2013: Oxbow 15-1

Gary Stevens, the jockey, guided Oxbow to take the lead right from the beginning and patiently anticipated a challenge. He continued to wait, and wait, and wait for it to materialize.

In this race, there were nine horses competing, with Orb, the Kentucky Derby winner, being the favorite with odds of 3-5. Oxbow, who had the second-highest odds, positioned himself on the rail at the beginning of the race, took the lead as they passed the stands, and proceeded to set a leisurely pace.

The winning time of 1:57.54 marked the slowest Preakness race since 1961. However, it’s worth noting that surpassing all competitors is what truly matters, isn’t it? At the age of 50, Stevens achieved the remarkable feat of becoming the oldest jockey to secure victory in the Preakness.

1983: Deputed Testamony 15-1

There was no doubt about the identity of the top horse at the 1983 Preakness, even though a spelling error occurred when completing the form.

Deputed Testamony, a horse born and bred in Maryland, was participating in his fifth race within an eight-week span at the Preakness. In his previous race, the Blue Grass Stakes, he had finished eighth. Donnie Miller Jr., a 19-year-old local boy, was the jockey for Deputed Testamony, as no other jockeys were interested in riding him.

During the race on a muddy track, Miller strategically positions Deputed Testamony along the rail, closely following the frontrunners. As a group of four horses takes the lead, Deputed Testamony stays with them. Eventually, he breaks away from the fading Desert Wine and triumphantly crosses the finish line, securing a three-length victory.

After spending $31 on a $2 bet, he ended up in a lackluster sixth place at the Belmont race. Unfortunately, Deputed Testamony sustained an injury during the 1984 City of Baltimore Handicap, leading to an early retirement.

Photo by Diane Bondareff / Associated Press
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