These Are The 10 Biggest Preakness Stakes Upsets Of All Time

Written By Dave Bontempo on May 19, 2023
Louis Quatorze, top Preakness upsets of all time, from

Preakness Stakes officials welcome the return of a cherished tradition: The Kentucky Derby winner trying to make it a double.

Mage is the first Derby champion since Authentic in 2020 to seek a Preakness Stakes parlay on Saturday. That brings more attention to this 1 3/16-mile, $1.5 million race, often the overlooked stepchild in the Triple Crown pecking order.

The 2023 Preakness does not look stacked for a significant longshot for any of you Kentucky horse betting fans out there. It thus may become the springboard for a potential Triple  Crown sweep by Mage in the Belmont Stakes June 10.

This brings significant appreciation for the upsets that have occurred in the race, which dates back to 1873.

Notable Preakness Stakes upsets

The Preakness has fewer of them for good reason.

Fields are smaller and horses who would be overlooked in a larger field get bet down.

While the Kentucky Derby ignited the horse-racing world with Rich Strike’s improbable 80-1 triumph last year, the Preakness eye-openers range only from odds of 10-1 to 23-1, the highest recorded.

Here are the top 10 notable Preakness upsets, including one that derived from the owner of a horse.

Bee Bee Bee, 1972

The slop caused Riva Ridge to flop.

Bee Bee Bee, a 19-1 longshot, thwarted Kentucky Derby winning Riva Ridge, who did not like this surface.

Riva Ridge went on to win the Belmont, giving him the rarity of taking the first and last legs of the Triple Crown, but not the Preakness. This has only happened 11 times.

The race is mentioned whenever rain is in the forecast for Preakness Day. Remember 1972. Remember Bee Bee Bee.

ALSO READ: Here’s The Exacta Bet I’m Placing On The 2023 Preakness Stakes

Master Derby, 1975

The largest-ever victorious Preakness longshot — 23-1 — turned the tables on Foolish Pleasure, who had beaten him soundly in the Kentucky Derby. Foolish Pleasure made a valiant late run but had too much to make up and finished second.

Closers coming up just short at the Preakness illustrate the importance of this 1 3/16-mile distance. It does not seem much shorter than the 1 1/4-mile Kentucky Derby at Churchill Downs, but it is enough.

Deputed Testamony, 1983

Sunny’s Halo had taken the 1983 Kentucky Derby and looked like a sharp favorite heading into the Preakness.

Deputed Testamony was making his fifth start in eight weeks and did not look imposing at 15-1.

But he ran the race of his career and lived a long life afterward. At the time of his death in 2012 at the age of 32, he was the oldest living winner of a Triple Crown race.

Deputed Testamony Preakness upset, from

Spend a Buck bypasses the Preakness, 1985

This was an upset based in the world  of business and administration.

Spend a Buck had captured two stakes races at newly re-opened Garden State Park in New Jersey in 1985. Connections would be awarded a $2 million bonus for any horse that swept two earlier Garden State stakes races, the Kentucky Derby and then the Jersey Derby on Memorial Day.

Spend a Buck’s connections opted for Garden State Park and skipped the Preakness. It sparked such an outrage that the Triple Crown would later award a $5 million bonus for any horse able to sweep it.

Both the bonus and Garden State Park eventually went away.

RELATED: Record-Breaking Handle, Other Takeaways From 2023 Kentucky Derby

Hansel, 1990

At 9-1, he turned the tables on Strike the Gold, who had beaten him in the Derby. Hansel gained a measure of revenge and denied any Triple Crown bid for Strike the Gold.

Hansel Preakness upset, from

Louis Quatorze, 1996

It wasn’t the odds of 17-2 that were the big story here. It was his rebound from the Derby.

Louis Quatorze finished 16th at Churchill Downs and had never won a stakes race going into the Preakness.

But when a horse shakes loose on the lead at Pimlico, he may stay in front. And that’s what happened.

Louis Quatorze Preakness upset, from

Charismatic, 1999

Say what? Charismatic had notched a stirring 30-1 upset at the Kentucky Derby, with Menifee rallying for second.

When the Preakness came two weeks later, Charismatic was 9-1 against the horse he had defeated.

His backers said “Thank you very much” and Charismatic prevailed again.

This ranked as one of the most dramatic drops between Kentucky  Derby and Preakness payouts in history.

At the Derby, Charismatic was 30-1 and Menifee was 7-1. They returned a whopping $727.80 for the exacta. Cat Thief was third and that $1 trifecta (which I had) paid $2,933.10.

Two weeks later, the same exacta combination occurred at the Preakness. But Charismatic and Menifee only paid $47.60.

Charismatic Preakness upset, from

Red Bullet, 2000

Fusaichi Pegasus, the Kentucky Derby winner, went off as the definitive odds-on favorite.

Red Bullet had skipped the Derby after finishing second in the Wood Memorial.

But the rest did him a world of good. Red Bullet looked fresher and pulled away in the  stretch

Who knew that skipping the Derby or the Preakness would become normal.

Rombauer and Early Voting, the past two Preakness winners, did not run in the Kentucky Derby. Twenty years earlier, however, this was big news.

Red Bullet Preakness upset, from

Shackleford, 2011

Kentucky fans remember Animal Kingdom capturing the Run for the Roses. Shackleford had never won  a stakes race and indeed seemed over his head against proven winners.

But he proved enough on this day, holding off the hard-charging Animal Kingdom to barely hold on at 13-1.

Shackleford Preakness upset, from

Oxbow, 2013

The field fell asleep on Oxbow, who had finished sixth behind Orb in the Kentucky Derby and was seemingly no threat. But he was allowed to take the lead in fractions, wasn’t pushed and, at 15-1, held on to win.

Oxbow Preakness upset, from

Notable Preakness fillies

Six fillies have captured  the Preakness. The past two are elite.

Rachel Alexandra not only beat the Kentucky Derby winner in 2009 Preakness, but stole the heart of his rider.

Calvin Borel, who had ridden Mine that Bird at Churchill Downs, made the practically unheard of move of  getting off the reigning Kentucky Derby champion to ride the filly against him in the Preakness. And he won.

Mine that Bird was second.

Borel thus won the Kentucky Derby and Preakness aboard two different horses.

Maybe there were no hard feelings. Borel later rode Mine that Bird in the Belmont.

Swiss Skydiver gave an exceptional performance in 2020. In seizing the Preakness, she recorded the second-fastest time in race history. Only the GOAT, Secretariat, bested her time.

The 1:53 mark set by Secretariat is now 50 years old.

Photo by Associated Press
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Dave Bontempo

Dave Bontempo is a multiple national award-winning boxing commentator and writer. He writes NFL betting columns for the Press of Atlantic City, iGaming Player and others. For PlayKentucky, he will focus on the world of Kentucky horse racing. 

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