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Old Glory: 5 Preakness Stakes Winners You Should Know About

Past Preakness stakes winners

As a sports fan, it’s always a norm to take a look back at the old days and relish the victories and performances our icons have done. From Michael Jordan’s memorable shot on Craig Ehlo to the 1980 “Miracle on Ice,” sports has its fair share of iconic moments.

With horse racing, it’s no different, even if the focus shifts to the racehorses more than the jockeys. 

One of the country’s biggest horse races, the Preakness Stakes, also has its fair share of winning moments. However, let’s steer clear of those moments and focus more on the icons, the racehorses.

Of course, a historical moment wouldn’t even be possible without these horses. With that said, let’s take a seat back and read about some of the previous winners of the Preakness Stakes:

2021 Winner – Rombauer

With odds set at 12-1, Rombauer was among the many favourites like Midnight Bourbon and Medina Spirit to win the 2021 Preakness Stakes. Rombauer was foaled on April 17, 2018. Bred by John and Diane Fradkin, Rombauer was raced as a homebred. 

Although the Fradkins were small breeders, they also had Ultrafleet. Ultrafleet failed to win in her races but became an excellent offspring producer. Rombauer came from Ultrafleet’s pedigree and was originally planned to be sold at an auction.

However, the pandemic struck and put a hold on Rombauer’s sale. The horse was then sent to Michael McCarthy for training.

With surprising results, Rombauer rose to fame. McCarthy was impressed with Rombauer’s strong performances in a special weight race at Del Mar and Keeneland’s Breeders Cup Juvenile. As one of the best preakness stakes previous winners, Rombauer’s main strengths are his stamina and intelligence. Those two qualities came in big as the horse won one of the biggest races in the country.

2020 Winner – Swiss Skydiver

Swiss Skydiver is a filly with chestnut colourings and a white star on her forehead. She was bred in Kentucky by Winstar Farm.

In 2018, Swiss Skydiver was sold for $35,000 to Kenneth McPeek and Peter Callahan. Swiss Skydiver’s name comes from Callie Rasnake, who is the owner’s granddaughter. Callie sent a video of herself skydiving over the Swiss Alps to her grandfather, and since then, the name has stuck. 

Swiss Skydiver showed why she was destined for greatness with a victorious first race at the Churchill Downs. She won 2nd place in a high-stakes optional claiming race two weeks later.

Swiss Skydiver’s biggest win was the 2020 Preakness Stakes. She was the first filly to win the race since 2009’s Rachel Alexandra. 

2019 Winner – War of Will

War of Will is a dark bay colt and was bred in Kentucky. Previously, Flaxman Holdings owned the horse. War of Will’s sire is War Front, a previous stakes winner, and his dam, Visions of Clarity, is also a known winner on the turf. With such a strong bloodline, it was expected that the horse would be bought immediately. 

However, War of Will is a living testament that a strong pedigree won’t necessarily help a horse get bought immediately at auctions.

Although War of Will was unsold, Norman Williamson bought him and trained him in Ireland. Currently, War of Will is owned by Gary Barber and trained by Mark Casse. 

The pedigree that potential buyers failed to see in War of Will would ultimately put him on top of the 2019 Preakness Stakes. War of Will showed everyone why Mark Casse considered him a “Superhorse.” 

2018 Winner – Justify

Perhaps one of the most challenging races in history, the 2018 Preakness Stakes was marred by bad weather and heavy fog.

A news outlet jokingly considered downgrading the muddy state of the track from a mere “sloppy” to a nightmarish “biblical.” As if it weren’t enough, the track was also filled with fog, significantly limiting visibility. 

Justify was the favorite to win the race, and he did so convincingly. With poor racing conditions and facing worthy rivals like Good Magic and Bravazo, Justify came out as the 2018 Preakness winner.

Justify is also hailed as one of the greatest horses to ever race. Justify has justified his greatness by being the 13th horse to win the American Triple Crown. He retired undefeated.

2017 Winner – Cloud Computing

The horse got his name from his owners, who were hedge fund managers who used similar financial terms in naming their horses.

Cloud Computing didn’t start racing until he was three years old. He won a maiden special weight race at the Aqueduct Racetrack on his debut. With an impressive performance, Cloud Computing would make everyone notice. 

However, as the 2017 Preakness Stakes loomed, he was not a favorite to win the race. Faced with fierce rivals and favorites in Always Dreaming and Classic Empire.

Cloud Computing beat the odds and won the 2017 Preakness Stakes. By doing so, he was only the fourth horse in the last 34 years to have won the stakes after not having placed previously. 


The five horses mentioned above capped off some of the biggest wins in Preakness Stakes history. Whether you’re an unintentional racer in Rombauer or one of the greatest horses in Justify, the winning moments these horses gave spectators are priceless.