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Best Preakness Stakes Winners of All Time

By Jeff Stinger

Horse Racing’s Triple Crown wouldn’t be complete without its middle crown in the Preakness Stakes. Dozens of amazing thoroughbreds have grazed and conquered the hallowed grounds of Baltimore’s Pimlico Race Course, but which racehorses left the most memorable impression in The Run for the Black-Eyed Susans?

Nitrobetting is here to help get those racebook bets across the finish line. This time, let’s count down the five best racehorses that have won the Preakness Stakes and what makes these magnificent beasts timeless legends at the Pimlico Race Course.

Top 5 Greatest Preakness Stakes Winners

Secretariat (1973)


Look no further than Secretariat to make most people’s lists of not just the best Preakness Stakes winners of all time, but simply the best racehorse to ever lived, hands down. To this day, Secretariat still holds the record for the fastest time of 1:53:00 at the Preakness since the race’s distance was updated to 1 13⁄16 miles in 1925. The Hall-of-Fame thoroughbred would go on to win the Belmont Stakes with relative ease in a few weeks from his monumental feat at the Preakness to cement its legacy as a legendary Triple Crown champion.

Affirmed (1978)


Another Triple Crown winner that is well-revered in the horse racing community is Affirmed, who also pulled off the Triple Crown win just half a decade after Secretariat’s run. The top-flight chestnut stallion sticks in a lot of people’s minds thanks in small part to its rival Alydar, which gave Affirmed a run for its money time and again. The two faced off for the eighth time at the Preakness and, just like the Kentucky Derby, it was Affirmed who beat out Alydar by a slim margin yet again. 

Spectacular Bid (1979)


Horse racing reached its peak thanks to the likes of Triple Crown Winners Secretariat, Affirmed, and Seattle Slew (who just missed our cut on this list) putting the sport at the forefront of the sports-loving fanbase. Before the decade would come to an end, though, one grey colt named Spectacular Bid entered its name into the hat of future Triple Crown legends. Although Spectacular Bid came up short at the Belmont to cut its Triple Crown bid short, its 1:54:20 finish at the Preakness was the fastest for its time before officials re-timed Secretariat’s official finish years later.

Rachel Alexandra (2009)


Fillies are rarely seen in the top level of horse racing nowadays, but one Rachel Alexandra broke from the mold and had one of the best one-two punches from the Derby into the Preakness of all time. Rachel Alexandra dominated both Churchill Downs and Pimlico and became just the fifth filly ever to win the Preakness Stakes. It was also the first time since 1924 that a filly had won the Preakness, and only the next horse on our countdown is the other female thoroughbred to have found success in the Preakness since.

Swiss Skydiver (2020)


The global pandemic era of horse racing wasn’t all doom and gloom, as in 2020, another filly made history when Swiss Skydiver won the Triple Crown’s Middle Jewel impressively. As of this writing, the Kenneth McPeek-trained steed has come the closest to breaking Secretariat’s record at the Preakness with a final time of 1:53:20. Horse racing has seen a noticeable uptick in viewership even amidst a global crisis, and it has Swiss Skydiver to partly thank for its slowly reviving popularity.

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