From Long Shots to Legends: 5 Surprising Moments in Preakness Stakes History

Discover five unforgettable moments in Preakness Stakes history - from legendary fillies to shocking upsets. See why this race continues to define horse racing greatness.

Five unforgettable moments in Preakness Stakes history - legendary fillies & shocking upsets, this race continues to define horse racing greatness.

From Long Shots to Legends: 5 Surprising Moments in Preakness Stakes History

May 13, 2025 - Every third Saturday in May, the eyes of the horse racing world turn to Pimlico Race Course in Baltimore, Maryland for the Preakness Stakes—the second leg of the coveted Triple Crown. While the Kentucky Derby dazzles and the Belmont defines distance, the Preakness delivers raw momentum, unexpected victories, and unforgettable moments.

The third Saturday in May is Pimlico's Preakness Stakes

At See Your Colors, where we honor the timeless tradition of racing through our handcrafted cast stone lawn jockeys, we know the stories behind these races are just as important as the finishes. Here are five surprising, lesser-known moments that remind us why the Preakness is a race like no other.

Riva Ridge came heartbreakingly close to Triple Crown glory in 1972, missing only the Preakness in the slop. But in doing so, he kept Meadow Stable alive—financially and reputationally—paving the way for Secretariat’s legendary run the very next year.

1.The Muddy Misstep: Riva Ridge’s Derailment in 1972

After a commanding win in the Kentucky Derby, many believed Riva Ridge was destined for Triple Crown glory. But the Preakness had other plans. On a rain-soaked track at Pimlico, the colt known for his speed couldn’t get traction in the slop. Enter Bee Bee Bee, a local long shot who took to the mud like a pro and stole the race in front-running fashion. It wasn’t absence that kept Riva Ridge from the Crown—it was mud, momentum, and a surprise performance that rewrote the narrative.

2. Shackleford Shocks the Field (2011)

Labeled a short-distance sprinter, Shackleford defied expectations by holding off Derby winner Animal Kingdom in a gritty stretch duel. His underdog victory reminded fans everywhere that Preakness winners aren’t always the favorites—they’re the fighters.

Rachel Alexandra - girl power!

3. Rachel Alexandra Makes History (2009)

She wasn’t just any filly—Rachel Alexandra was a phenomenon. Just two weeks after winning the Kentucky Oaks by 20 lengths, she became the first filly in 85 years to win the Preakness. Her groundbreaking victory helped reshape the conversation around gender in racing.

4. American Pharoah Races Through a Storm (2015)

Torrential rain turned the 2015 Preakness into something out of a movie. But it didn’t stop American Pharoah, who burst through the storm like a machine—on his way to becoming the first Triple Crown winner in 37 years.

Did you see the 1980 Preakness? What do you think REALLY happened?

5. Codex vs. Genuine Risk: A Controversial Finish (1980)

In one of the most disputed finishes in modern Preakness history, Codex defeated Kentucky Derby winner Genuine Risk - but not without allegations of interference. The resulting controversy led to lawsuits, investigations, and a permanent mark on racing history.

What It All Means

These aren't just horse races—they’re moments that shaped a sport, sparked conversations, and inspired generations of fans. The Preakness Stakes may only last two minutes, but its stories last forever.

📸 Journalism (8/5) — Trained by Michael McCarthy and ridden by Umberto Rispoli, this Santa Anita Derby winner returns just two weeks after a strong runner-up finish in the Kentucky Derby. Backed by powerhouse owners and boasting a field-best 108 Beyer, he's the one to watch. 🏇🔥

And for those of us who feel connected to this world—the vibrant silks, the proud stables, the heritage of it all—these stories hit different. They’re part of what inspired the creation of See Your Colors, where we make art-quality, hand-painted lawn jockeys in honor of the very traditions the Preakness upholds.

Whether you’re racing, cheering, or simply admiring the artistry of the sport, the Preakness reminds us all that even long shots can become legends.

Want more stories from the track—and the lawn?

• Read more on the Blog.

• Thinking about a custom lawn jockey to match your silks? Find us at your favorite track or schedule a delivery to bring your colors to life.

• Explore our Gallery to see some the silks of our beloved famous horses displayed on a lawn jockey.

By Dawn Hartfelder, MBA Candidate

Dawn Hartfelder is a Marketing Analytics Specialist at Sweet Media and an MBA candidate at Arizona State University. A veteran of New Jersey’s largest nonprofit organizations, she’s fluent in navigating chaos and cutting through noise.

She’s also the world’s greatest lawn jockey painter - bringing racing’s most iconic silks to life in cast stone. Her latest blog, From Long Shots to Legends, blends analysis with reverence for the sport.