The Kentucky Derby has left quite a trail in its 149 runnings.

While dust certainly settles on the track, artifacts associated with the Run for the Roses can linger for decades.

Stories and memories live on in the countless collectible Kentucky Derby cups that fill cupboards or hats that rest in closets, but some objects carry a whole different weight and symbolism.

A few years ago Jessica Whitehead, the curator of collections for the Kentucky Derby Museum, told me the American flag that flew over Churchill Downs in 1937 was one of the most celebrated artifacts in the museum’s 20,000-piece collection. The Kentucky Derby was nearly canceled that year because the Ohio River flooded and devastated Louisville but the race went on because Kentucky’s governor at the time delivered a morale-boosting speech insisting the event was a symbol of unity.

Like that flag, so many of the objects in the museum seem ordinary or unremarkable, until you think about what they have to say about the era they’re from.

“Objects are so special because, they’re literal touchstones for history, and they’re literal touchstones for memory,” Whitehead said.

Kentucky Derby history runs in tandem with American history, so much of what’s happening in the world can be remembered through the lens of this historic race.

In honor of the 150th running, Whitehead has compiled a book titled “The History of the Kentucky Derby in 75 Objects.” Inspired by that 1937 flag, I asked her to share a few other stories hidden among the museum’s Kentucky Derby artifacts.  

“If these artifacts could speak,” she gushed.

Here is a quick look at some extremely humble but very telling pieces of Kentucky Derby history.

1870s: Renderings of the original Clubhouse

Images of the earliest days of Churchill Downs, which was known originally as The Louisville Jockey Club, are difficult to come by. Photography was extremely limited when the track opened in 1875, Whitehead said, so one of the best ways to understand what life was like at the track is hand-drawn renderings.

The Clubhouse was the most exclusive part of the track in the late 19th century, and it was where all the movers and shakers of the day practiced their social sport in between races. These drawings, which are more than a century and a half old, offer a glimpse into what high society looked like for the earliest Kentucky Derby-goers. The Clubhouse had a kitchen all its own, and it was the only part of the track that had indoor bathrooms.

The drawings nod to both the Kentucky Derby experience in its earliest days and the technology of that period. The building was designed in a Carpenter Gothic style by John Andrewartha, a prolific architect in Louisville. The intricate detail in the trim on the structure was only possible because of scroll saws, which were semi-new tools of the day.

The Clubhouse wasn’t part of the Kentucky Derby for long. Once the Twin Spires grandstand was constructed in 1895, it was used for storage or as a residence for the track’s superintendent. By the 1910s it was demolished to make room for barns and outbuildings.

1875: Aristide’s booties

Even with all the glittering trophies and priceless artwork, Whitehead says some of the most prized objects in the collection look humble. The ankle boots once worn by the first Kentucky Derby winner Aristides tell a story of craftsmanship and how racehorses were cared for in 1875.

“These are just (hide) and leather little booties, and if you haven’t ever seen 19th-century horse gear, you might not know what you’re looking at,” Whitehead said.

Aristides wore these anklets in the same way that modern horses have gauze wrapped around their ankles. They would have been touched by Oliver Lewis, the Black jockey who won the first Derby, and by his celebrated Black trainer, Ansel Williamson. The booties are among the oldest objects in the museum’s collection.

“We don’t know if they were worn in the [first Kentucky] Derby,” Whitehead said. “But the fact that they were saved and hallowed this way suggests that certainly, he would have worn them at an important time in his career.”

1896: Isaac Murphy’s grave marker

Isaac Murphy’s legacy is imperative to the history of the Kentucky Derby, but for decades his grave was lost.

His gravestone helps tell the story of how the Jim Crow era, which enforced segregation, forced out the Black jockeys, who powered the racing industry in the late 19th century, Whitehead said. Murphy was a three-time Kentucky Derby winner and the son of a formerly enslaved person in Fayette County. He rode in 11 Kentucky Derby races.

When he died in 1896 — the same year that Black horsemen started getting pushed off the tracks by their white counterparts — Murphy was buried in African Cemetery No. 2 in Lexington, which fell into disrepair in the early 20th century. Grave markers were kicked down, destroyed, and moved from their original spots. His grave was considered lost until it was rediscovered in the 1960s. His body was then moved to a place of honor in the Kentucky Horse Park in Lexington.

The original gravestone was then restored and donated to the museum’s collection.

1913: Donerail’s scrapbook

Donerail, who won the 1913 Kentucky Derby, was the longest shot to ever win the race at 91-1 odds. His owner, Thomas Hayes, was so thrilled kept a scrapbook about the horse’s racing career, which is now part of the museum’s collection.

Hidden in those pages is the story of the track’s survival and hometown pride.

Today the Kentucky Derby is an international sensation, but it wasn’t always that way. Churchill Downs was in financial turmoil at the end of the 19th century, and it looked like the Kentucky Derby might have run its course. Matt Winn, the former director of Churchill Downs, gets most of the credit for reviving the track and the race, but Whitehead said, he also got a lot of help from some incredible horses, like Donerail.

“These were stories that spoke to more than just horse racing fans or gamblers,” Whitehead said. “These were stories that started to speak to the American public in ways that were beyond just horseracing.”

Donerail’s jockey, Roscoe Goose, had grown up in Louisville on Third Street near Churchill Downs, and there was an immense sense of local pride swelling around his Kentucky Derby win. Inside the scrapbook is a letter to Hayes from a local shopkeeper, who states that they were so thrilled they decorated the shop in Donerail’s colors.  

1934: Brookmeade Stable Jockey Silks

Isabel Dodge Sloane owned Brookmeade Stable and her horse Cavalcade, won the Kentucky Derby in 1934. These are the jockey silks worn by Mack Garner that represent her colors and win.

A man’s jockey silks might seem like an unusual symbol of women’s strides in the male-dominated horseracing industry, but Whitehead says these point to the story of the earliest women horse owners involved in the Kentucky Derby. They first came on the scene in the early 20th century, but it wasn’t until the 1920s and 1930s that women owning racehorses became a more acceptable practice, particularly on the East Coast.

Sloane was also a fashion icon, who helped set the stage for women’s sportswear at the track.

1958: Tim Tam’s horseshoes

Today, Latin American jockeys are a crucial part of horseracing, but that wasn’t the case in the earliest Kentucky Derby races. José “Joe” Rodriguez was a Cuban trailblazer for Latinx jockeys in the United States throughout the 1920s and 1930s, but a Latin American jockey wouldn’t win the Kentucky Derby until Ismael “Milo” Valenzuela road to victory on Tim Tam in 1958. The Kentucky Derby Museum has Tim Tam’s horseshoes in its collection.

“He was the first Latin American winner of the Kentucky Derby, which of course has huge ramifications on the history of the sport,” Whitehead explained. “After that, the trend went significantly toward Latin, Central American and South American horsemen.”

Valenzuela also won The Preakness in 1958. His earnings in his career topped $20 million.

2020: Hats and masks

The museum focuses on preserving the Kentucky Derby’s past, but that also involves collecting objects that help tell its story in the future. The past decade has seen many highs and lows between the COVID-19 pandemic, the racial justice protests, and two disqualifications of winners, among other circumstances.

“We’re still so close to it, that I think we’re going to be trying to understand this period for a long time,” Whitehead said.

It’s always difficult to guess what artifacts will be important down the line, Whitehead said, but the hats and masks worn at the races in 2020 and 2021 because of the COVID-19 pandemic undeniably speak volumes about the culture of the era.

“People are going to look back at 2020 and 2021, and go ‘What the heck was going on there,’” Whitehead said. “And we’re really fortunate to have some examples in our collection that can help shed light on that and tell those stories later on.”

Features columnist Maggie Menderski writes about what makes Louisville, Southern Indiana and Kentucky unique, wonderful, and occasionally, a little weird. If you’ve got something in your family, your town or even your closet that fits that description — she wants to hear from you. Say hello at mmenderski@courier-journal.com or 502-582-4053. Follow along on Instagram @MaggieMenderski.