The Preakness Stakes is an annual Thoroughbred horse race held annually on the third Saturday of May at Pimlico Race Course in Baltimore, Maryland. It is the second jewel in horse racing’s Triple Crown. The Preakness is held two weeks after the Kentucky Derby at Churchill Downs in Louisville, Kentucky, and three weeks before the Belmont Stakes at Belmont Park in Elmont, New York.
In each race, horses are graded with odds predicting how they will fare. Bettors use these odds to determine how they will wager. Will they put their money on the “sure thing” or will they bet the “long shot?” It is not as straightforward as it may seem, though. Historically, the oddsmakers’ favorite only wins about one-third of the time. Long shots can and do win big races. Here are the six biggest long-shot horses to win the Preakness Stakes.
1975: Master Derby
- Odds: 23-1
- Jockey: Darrel McHargue
- Trainer: Smiley Adams
- Owner: Golden Chance Farm (Robert E. Lehmann)
- Track Condition: Fast
The 1975 race marked the 100th running of the Preakness Stakes. Master Derby had the seventh-longest odds in the ten-horse field that would run this momentous race. Despite his fourth-place finish at the Kentucky Derby, the colt didn’t attract much attention for the Preakness Stakes. The majority of fans and bettors, instead, set their sights on Foolish Pleasure, the acknowledged favorite of the 1975 Preakness.
Foolish Pleasure won the Kentucky Derby and seemed poised to extend his winning streak. Secretariat had won the Triple Crown two years earlier, and many predicted Foolish Pleasure to be the next Triple Crown winner. However, since 1919, only 13 horses have won the Triple Crown. 1975 would not feature a Triple Crown winner.
Master Derby came out of the gate strong. The colt occupied third place for the first half of the race and then moved into the lead. Foolish Pleasure, the oddsmakers’ favorite, made a strong push at the end, but Master Derby held him off and won the race by a length. Master Derby remains the horse with the biggest odds to win the Preakness Stakes.

Pimlico Race Course is the home of the Preakness Stakes, held on the third Saturday in May each year.
1925: Coventry
- Odds: 21-1
- Jockey: Clarence Kummer
- Trainer: William B. Duke
- Owner: Gifford A. Cochran
- Track Condition: Fast
Coventry was trained by a French trainer named William Duke. Many Americans, swelled with national pride, believed that no French-trained horse could beat horses trained by Americans. They were wrong.
Nationalistic feelings aside, Coventry was a long shot for a good reason. The horse fared quite poorly at a race the weekend before the Preakness. However, the colt was saving his best performance for Pimlico Race Course.
At the beginning of the 1925 Preakness, a horse named Backbone came blazing out of the gates. This extraordinarily fast pace could not be maintained, though. Backbone and the other horses faded, allowing Coventry to move into the lead and win the race by an amazing four lengths over Backbone.
This would be Coventry’s only major victory. In his next race, the Withers Stakes at New York’s Aqueduct Racetrack, Coventry broke down. He was retired to stud.

The Woodlawn Vase became the official trophy for the winner of the Preakness Stakes in 1917.
©Harris & Ewing, photographer / Public domain – Original / License
Note: there are ties for both the third and the fourth longest odds to win the Preakness Stakes.
1926: Display
- Odds: 19-1
- Jockey: John Maiben
- Trainer: T. J. Healey
- Owner: Walter J. Salmon, Sr.
- Track Condition: Fast
The year after Coventry’s improbable victory at the Preakness, another long shot would be found in the winner’s circle.
Display had a decorated racing career, but he never emerged from Man o’ War’s shadow. Man o’ War was Display’s older brother and is considered the greatest racing Thoroughbred of all time. However, Display had a distinguished career himself, including a win at the 1926 Preakness Stakes.
In the race, Display started well back from the leaders. The starting pace was unsustainable, though. Display moved to the front alongside a Thoroughbred named Blondin as the early lead horses faded. Display held off Blondin, winning by a head.

Oden Bowie, governor of Maryland from 1869-1872, named the Preakness Stakes in honor of a colt named Preakness.
©Tom at English Wikipedia / Public domain – Original / License
1972: Bee Bee Bee
- Odds: 19-1
- Jockey: Eldon Nelson
- Trainer: Del W. Carroll
- Owner: William S Farrish, III
- Track Condition: Sloppy
Riva Ridge was the talk of the horse racing world in 1972. Many believed the colt was a legitimate Triple Crown contender. He certainly came close. Riva Ridge won the Kentucky Derby and the Belmont Stakes in 1972. If it weren’t for the rainy conditions in Baltimore on May 20, 1972, Riva Ridge may well have etched his name in history as a Triple Crown winner. However, the sloppy track conditions at the Preakness proved too much for the colt.
Heavy rains turned the track at Pimlico Race Course into a muddy mess. Riva Ridge balked at the slop, and that is when Bee Bee Bee took control of the race.
Bee Bee Bee was foaled in Maryland, and Pimlico was his home track. Along with his home-field advantage, the colt proved that he was a mudder extraordinaire. Bee Bee Bee won the race, finishing ahead of No Le Hace by 1 ½ lengths. Riva Ridge finished fourth, 5 ¼ lengths behind Bee Bee Bee.
Bee Bee Bee’s 1972 victory tied Display’s finish in 1925 as the third-longest odds to ever win the Preakness Stakes.

The Preakness Stakes have been nicknamed “The Run for the Black-Eyed Susans” because a blanket of Maryland’s state flower is placed across the withers of the winning colt or filly.
©iStock.com/Dopeyden
1983: Deputed Testamony
- Odds: 15-1
- Jockey: Donnie A. Miller Jr.
- Trainer: J. William Boniface
- Owner: Francis P. Sears Jr.
- Track Condition: Sloppy
The animal’s strange name was reportedly a double misspelling of the intended name, “Disputed Testimony.” It was purportedly meant as a play on the names of his sire (Traffic Cop) and dam (Proof Requested). No one is quite sure how the name was misspelled so badly on the form. After the race, one New York Times reporter quipped, “Good spellers and serious horseplayers both received a jolt today …”
Deputed Testamony was considered such a longshot that experienced jockeys all turned down the mount. Finally, a 19-year-old local man named Donnie Miller, Jr. accepted the assignment.
Rain made for sloppy track conditions in the 108th Preakness Stakes. Deputed Testamony worked his way into the lead group. The race leader, Desert Wine, faded in the stretch, and Deputed Testamony won by three lengths.

Sloppy track conditions can change everything at the Preakness.
2013: Oxbow
- Odds: 15-1
- Jockey: Gary Stevens
- Trainer: D. Wayne Lukas
- Owner: Calumet Farm
- Track Condition: Fast
Thirty years after Deputed Testamony’s win, Oxbow would tie him for the fourth-longest odds ever to win the Preakness Stakes.
The track condition was considered fast for the 138th running of the Preakness, but the race itself would be anything but fast. The winning time of 1:57.54 was the slowest Preakness finish since 1961.
Oxbow set that slow pace right from the gate. No challenger in the nine-horse field ever took the lead from the colt, including Orb, who had won the Kentucky Derby two weeks earlier.
Oxbow won by 1 ¾ lengths over Itsmyluckyday. Orb, the banker for the 2013 Preakness Stakes, crossed the finish line in fourth, a staggering nine lengths behind Oxbow.
Riding Oxbow to an improbable victory, Gary Stevens became the oldest jockey to ever win the Preakness Stakes at 50 years old. That record would only stand for five years, though. In 2018, Mike Smith became the oldest jockey to win all three races of the Triple Crown at age 52.

The Preakness Stakes is the second jewel in the coveted Triple Crown.
©iStock.com/olgaIT
Thank you for reading! Have some feedback for us?
Contact the AZ Animals editorial team
Thank you for your feedback!
We appreciate your help in improving our content.
Our editorial team will review your suggestions and make any necessary updates.
There was an error submitting your feedback. Please try again.