Big Hats, Bigger Stakes: An Insider View of Preakness

Correspondent Rob LeDonne reports on the action—and the personalities—at the Preakness Stakes.

Preakness 148 In The 1/ST Chalet Hosted By 1/ST At Pimlico Race Course, Baltimore, MD
Lana Ray and guest. Getty Images for Preakness 148

There are just a few hours to go before the day’s big race, and broadcast journalist Gayle King has been noshing on Wagyu burgers at the Owner’s Chalet at Baltimore, Maryland’s Pimlico Race Track. “I will never turn down a good burger,” she tells me, asking for my name again. “It’s Rob, right?” she sings, before repeating herself, putting a dollop of enthusiasm on it.

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King is here for the 148th running of the Preakness Stakes, the second race of the Triple Crown. Much like jazz or cowboy worship, it’s a long-running American tradition that attracts a wide range of adherents. Walking around, one quickly realizes the Preakness is an event that lures everyone from demure ladies in flowing dresses and sometimes-monumental hats to rowdy college students there to get tanked on cheap beer.

Preakness 148 In The Infield Hosted By 1/ST At Pimlico Race Course, Baltimore, MD
Time to dance? Getty Images for Preakness 148

“I love the fact the race is held where it is, in the neighborhood that it is,” King tells me when I ask the groundbreaking question: What brought you out here today? (I’m eagerly awaiting my Pulitzer.) “This race,” she adds, “sends a message to the community that you matter and gives a boost to the neighborhood. Plus, you have a nice group of people here.”

Very nice, and very drunk. Moments later, a tipsy group of feather-hatted women of a certain age descends upon King. They are initially reverent, as if meeting the Pope.

“Hello, we love you,” one of them garbles to the morning anchor. “You say that to all the girls?” asks King, as naturally charming as you’d imagine. “Noooo,” another squeals. “We admire you!”

They ask for a picture, and King obliges. The taking of said photo turns into a massive undertaking involving multiple poses as well as numerous confused grimaces as the group attempts to navigate the mysteries of an iPhone camera.

The atmosphere at Pimlico on race day is a hodgepodge that encompasses party, concert and casino. On one end of the property are the spectator stands where ticketed gamblers and revelers view the race. On the other, there is the Preakness Live—a mini-Coachella featuring Bruno Mars as headliner. Smack in the middle of Pimlico’s circular mud track, accessible only by a moveable land bridge, is the Owner’s Chalet, where I encountered king. It’s also where thoroughbred racing fans can sip the race’s famed cocktail, the Black-Eyed Susan, which is named for that flower’s resemblance to the Viking Poms placed around the winning horse’s neck and poured as if the alcohol is water and spectators are fish.

“This is a total first for us,” says Tucker Halpern, half of the dance-duo SOFI TUKKER alongside Sophie Hawley-Weld, who is performing later today. Having flown in from Vegas to celebrate Sophie’s birthday (of course “It was absurd”), the two recently played the real Coachella and will soon make appearances at Governor’s Ball and Lollapalooza.

A woman in a tube top stands next to a man in a baseball cap
LeDonne, speaking to electronic duo SOFI TUKKER. Arseny Jabiev

“It’s a little bit of a mindfuck,” he tells me. “Every festival has its own vibe and identity, but it can all blend together. Sometimes an outdoor festival can feel like any other festival. But with the hats and fashion today, this feels very, very unique.”

Two women stand close to one another in fancy hats.
A duo poses at the 148th running of the Preakness Stakes. Arseny Jabiev

Yes, the hats. Much like the faux beards at a Santa Claus convention, the women’s race day hats come in all shapes, sizes and colors, topped with everything from traditional flowers and feathers to the unexpected.

A woman wears feather sunglasses
A Preakness reveler in subtle eyewear. Arseny Jabiev

Forget your hat? No need to fear: there’s a hat vendor on-site.

Even the music executive Kevin Lyles is wearing a hat, albeit one in the form of a baby blue baseball cap stitched with the Louis Vuitton logo.

“This is Baltimore’s Super Bowl,” he tells me. A native of the city—he grew up 10 minutes away—Lyles first attended with his dad. These days, when he’s not helping make Megan Thee Stallion a superstar as CEO of 300 Entertainment, he’s one of the city’s biggest champions. (King also told me she’s in attendance because of Lyles).

300 Entertainment was acquired for $400 million by Warner Music Group a few years ago and unsurprisingly, Lyles has been having the time of his life since. “Earlier today I went to Caves Valley Golf Club,” he says, mentioning that he shot an 87. “Then we had lunch at the Four Seasons, and now I’m here.”

Inside the Owner’s Chalet, there are large platters of crab cakes, crab legs, crab dip, lobster rolls and duck tacos.

Crab cakes, a staple of Baltimore cuisine, were copious. Arseny Jabiev

Toward the end of the day, the entrees are swapped out for endless slices of chocolate cake topped with lusciously-thick frosting. Bobby Flay, who I hear is in attendance, would be proud. I fill my plate twice and start feeling the need to nap.

But much like there’s no crying in baseball, there’s no rest at the track. Today, everyone wants to know who you’re betting on and if you’re winning or losing, but you can only place cash bets, the ATMS are only dispensing 100s and I survive on a writer’s salary. The main race kicks off at 7 p.m., and National Treasure (ridden by Hall of Fame jockey John Velazquez) is this year’s winner. Nicolas Cage is somewhere smiling.

148th Preakness Stakes
Jockey John Velazquez astride National Treasure at the 99th Black-Eyed Susan Day hosted by 1/ST at Pimlico Race Course, in Baltimore, MD. Paul Moigi / Getty Images

I push past members of the Baltimore Ravens snapping selfies and smoking cigars, and catch up with Belinda Stronach, the master of ceremonies and CEO of the Stronach Group. She tells me she’s trying to update certain aspects of the day, which could explain the bevy of influencers in attendance. One, who said the race has “good food and good alcohol” tells me about a country-rap music video and song dedicated to the Preakness.

A woman smiles in a group of people facing away from the camera
Chatting with Belinda Stornach, who wants to “modernize” the race. Arseny Jabiev

“The Maryland Jockey Club (the organization behind the race) was established in 1743, so that makes it the oldest sporting club in America,” Stronach explains. “I think we’ve come a long way and we’ve shaken things up, which some people love and some people don’t love. I think it has to happen. We’ve got a ways to go still. I’m not happy where we’re at yet, but we’re getting there and changing the industry.”

By the time the day’s winners finish celebrating and the losers who gambled away their kids’ college funds have finished crying, Mars takes the mic on the Preakness Live stage. Unfortunately, this happens just as ominous storm clouds give way to heavy rain.

He doesn’t seem to mind, and the weather gives Mars the vibe of a sacrificial artist. At the bar, the tenders fill plastic shot glasses of tequila and pour even more Black-Eyed Susans. I put on a poncho. Dancing in the downpour, Mars jumps to the mic to proclaim, “We’re not gonna let the rain stop the party!”

Big Hats, Bigger Stakes: An Insider View of Preakness