Here Are The Biggest Preakness Long-Shot Winners … Ever

Written By Darren Cooper on May 19, 2022

The horse racing world is gripped by long shot fever.

That’s what happens after Rich Strike, at 80-1 odds, won the Kentucky Derby, making him the second-longest, er, long shot to ever win the race.

Rich Strike isn’t running at the Preakness Stakes Saturday in Baltimore. Saturday’s second jewel of the Triple Crown is a nine-horse field and of course, there are favorites (Epicenter), and longshots (Happy Jack) to bet on.

The easiest way to bet on the Preakness in Virginia is with the TVG app. It’s specifically designed and caters to horse betting. Click on the link below to see special offers for the upcoming premier racing event.

No horse with 80-1 odds has ever won the Preakness before. Here are the six biggest long shots to ever win Baltimore’s big race.

1975: Master Derby, 23-1

This is one of those stories where Foolish Pleasure had convincingly won the Kentucky Derby and then everyone assumed he was going to win the Triple Crown.

It happens every year.

While the public went big on Foolish Pleasure, few noticed Master Derby who had run well at Churchill Downs finishing fourth and had victories in the Louisiana Derby and Blue Grass Stakes.

Master Derby hung on the rail through the first half of the race in third, then joined a group of four horses abreast in the lead. In the stretch run, Foolish Pleasure gets right on Master Derby, but Master Derby senses him and gets to the wire by a length.

Master Derby lived to be 27 and is still the horse with the biggest odds to win the Preakness.

1925: Coventry, 21-1

There was a lot of doubt about Coventry a century ago, as he was trained by William Duke from France. No way a Frenchman’s methods could top the American style. Could he?

Coventry had lost badly at the Wood Stakes the weekend before the Preakness. The Daily Racing Form called this race full of drama and blamed the lead horses, particularly Backbone, for setting a ridiculous early pace.

This allowed Coventry to race comfortably and win by four lengths as everyone else faded. It was the only race Coventry won of the five he started. In his next race at Aqueduct, he broke down and was retired to stud.

1926: Display 19-1

Display was the little-known brother of Man o’ War and had a successful racing career until he was six.

This Preakness started with the crazy setting on high. Canter wouldn’t get in to his post, then kicked Navigator. Another horse, Mara, reared and got stuck on a temporary inside rail.

When the race finally started, Canter, along with Rock Man and Dress Parade, took the lead, but maybe from all that early energy expended, they all faded and this turned into a long stretch battle between Display and Blondin.

Display never tired and held off Blondin for the Preakness win. Display went on to multiple wins as a four and five-year-old.

1972: Bee Bee Bee 19-1

Riva Ridge was the Superstar horse of 1972, winning the Kentucky Derby and – like happens so often – was considered a lock for the Preakness.

Bee Bee Bee was Maryland-born and had won two minor races at Pimlico. This was his home track and when rain made the track sloppy, Riva Ridge balked.

Bee Bee Bee, a mudder if there ever was won, won by nearly two lengths in one of the biggest Preakness upsets ever.

2013: Oxbow 15-1

Jockey Gary Stevens piloted Oxbow to the lead at the start and waited for a challenge to come.
And waited.
And waited.

This was a nine-horse field with Kentucky Derby winner Orb the 3-5 favorite at post-time. Oxbow, who had the second-highest odds in the field, moved to the rail at the start of the race, passed the stands in the lead and set a slow pace.

His winning time of 1:57.54 was the slowest Preakness since 1961. But hey, as long as you beat everyone else, right? At age 50, Stevens became the oldest jockey to win the Preakness.

1983: Deputed Testamony 15-1

The name was spelled incorrectly when filling out the form, but there was no mistake about who the best horse was at the Preakness in 1983.

Deputed Testamony was making his fifth start in eight weeks at the Preakness. He was Maryland-born and Maryland-bred. He had finished eighth in the Blue Grass Stakes. His jockey, Donnie Miller Jr., was a 19-year-old local boy because no one else wanted the mount.

In the race, on a sloppy track, Miller puts Deputed Testamony on the rail and is stalking the leaders. When a lead group of four emerges, Deputed Testamony goes with them. He pulls away as Desert Wine fades back and wins by three lengths.

He paid 31 bucks for a $2 bet and finished a nondescript sixth in the Belmont. Deputed Testamony suffered an injury in the 1984 City of Baltimore Handicap and was retired.

Photo by Diane Bondareff / Associated Press
Darren Cooper Avatar
Written by
Darren Cooper

View all posts by Darren Cooper