At the Strangest Kentucky Derby in History, Old Traditions Clash With Modern Struggles

Decadence and depravity take a year off.

The Kentucky Derby, 2020 edition | Horsephotos / Contributor/Getty Images
The Kentucky Derby, 2020 edition | Horsephotos / Contributor/Getty Images

For two minutes every year, all eyes are on Louisville. This year, those eyes have lingered much longer.

The home of the equine bacchanal we call the Kentucky Derby didn’t have its traditional week of oversized hats and over-consumed bourbon. This year, Louisville became known as something far heavier than the host of America’s greatest horse race. 

The city has been a flashpoint for protests since March, when Breonna Taylor was shot and killed by police in her home. But despite the simmering anger and pleas for change as the Attorney General weighs charging police in Taylor’s death, the Kentucky Derby announced it would run with limited spectators. 

Then, two weeks before the race, Churchill Downs announced no fans would be allowed inside. It seemed Derby week was effectively cancelled.

Still, with travel already booked, I decided to survey the scene. What I found was a Derby week unlike any before, and a city that offered a perfect snapshot of this American moment.

Downtown Louisville | Matt Meltzer

“We usually sell out a year in advance, starting at $1,099 a night, with a three-night minimum,” Skip James, VP of sales at the 1,200-room Galt House Hotel, tells me over breakfast. “I think we have 100 rooms booked tonight. Maybe 250 on Saturday.”

His tone is unexpectedly cheerful for a man who’s spent six months fielding coronavirus cancellations right after the hotel completed an $80 million renovation. The property sits right on the Ohio River, in the midst of a semi-deserted downtown.

After breakfast, I meet Adam Skiles outside the Galt House. He’s the only man on the street, and, decked out in a blue sports coat, slacks, and a straw fedora, looks like he’s fallen through a wormhole at Churchill Downs circa 2019.

“There are some here who think this race shouldn’t be run, and it’s not because of corona.”

“Sorry our downtown isn’t quite itself,” the Trolley de’ Ville tour owner, says as he drives me past blocks of plywood-covered windows. “People are kinda all waiting to… see what’s gonna happen.”

He says it in that delicate way people mention unpleasant things without really mentioning them. But by “see what’s gonna happen,” he didn’t mean “see who won the 146th Kentucky Derby.”

“There are some here who think this race shouldn’t be run, and it’s not because of corona, necessarily,” Skiles continued. “We’re not running tours now. We did for a while, then we had people yelling things at our trolleys. One time a group of people surrounded it and stared in the window. So we thought we’d wait until all this is over.”

We spent the afternoon traversing the Kentucky Bourbon trail, where a smattering of people filled the socially distanced tasting rooms at Bardstown Bourbon, Lux Row, and others. Jim Beam and other big names were still closed due to the pandemic.

“Derby week usually, you can’t even get in here,” Bardstown Bourbon’s VP of hospitality Daniel Calloway tells me. “This year… you need to come back.” It’s a refrain I hear from literally everyone I meet in Louisville.

Jockeys don masks at Churchill Downs | Horsephotos / Contributor/Getty Images

The Wednesday before the Derby, I was racing the COVID-era last call of 10pm at Jockey Silks Bourbon Bar inside the Galt House. My third Old Fashioned was going down smoothly when I spotted a man with bright white hair and a powder-blue shirt approaching the bar.

“Bob Baffert, nice to meet you,” he said before turning to the bartender. “Ice water, please.” This would be akin to Bill Belichick bellying up to the bar next to you during Super Bowl week.

“Usually if I’m in here during Derby week, people are all coming up to take selfies. It’s fine, but makes it hard to work, you know?” he said. The two other tables of people in the bar took exactly zero notice he was there. “In some ways, this is easier.”

So easy, in fact, Baffert sat drinking ice water with me for the better part of an hour. “We got a nice horse this year,” he said modestly. “But that Tiz the Law, he’s a man among boys out there.”

“You hear ‘My Old Kentucky Home,’ and that crowd erupts... that’s what I come here for. This year will be weird, yeah.”

Upstairs the next morning, a small man moved with intense purpose from weight machine to weight machine at the Galt’s rooftop gym. It was Mike Smith, who won the Triple Crown aboard Justify in 2018, and at age 55 was about to ride in the Kentucky Derby for the 26th time. Just to continue the analogy, this would be like walking into your hotel gym during the Super Bowl and seeing Tom Brady an hour deep into TB12.

“I warm up with a five-mile run,” Smith told me later, coincidentally also over ice water. “Then, I like to do all the machines, 25 reps each. Then go back and do it again. Then, maybe do it a third time.”

“Big Money” Mike doesn’t seem too phased by slimmer crowds this year, aside from missing the fans. Like Baffert, he says it makes it easier for him to prepare for the race.

“This… this isn’t the same,” he says of this year’s Derby. “When you get in there, and you hear ‘My Old Kentucky Home,’ and that crowd erupts, that’s what I come here for. This year will be weird, yeah. But hit me up tomorrow, we’ll be over at Jeff Ruby’s... you should come have a drink.”

In some years, this would be the beginning of an epic story about partying with the best jockeys in the world. But in the age of COVID, nearly everyone’s night ends at 10.

A peaceful protest takes place in Louisville in June. Demonstrations around the Derby remained largely peaceful. | Fibonacci Blue/flickr

It is Derby Day, and I’ve returned to Jockey Silks -- partly because it’s the only bar downtown I know that's open, partly because it seems to have some semblance of a festive atmosphere. A slow stream of people in Derby finery trickle through wearing masks, determined to dress up. 

I’m sitting with Alan Rupp, owner of Kern’s Kitchen, makers of the nutty, chocolatey Derby Pies. A reporter on television is standing in front of a group of protestors at Churchill Downs, which he mentions sits in a predominantly Black neighborhood. Most people never hear this.

“This is Derby week,” Rupp says, watching the reporter. “We’re not supposed to be talking about riots.”

“Excuse me,” a voice from the table behind us says. “I couldn’t help but overhear you. There won’t be any riots.”

She is a Black woman, immaculately put together in a purple dress with small, yellow glasses. “My family are the ones organizing [the protest]. My grandma lives right there. People are talking about bringing their kids out there. If there’s any riots, it didn’t come from us.”

Rupp nods. Everyone in the Louisville I’ve seen -- the one where the Derby must go on -- has been accentuating the positive, if only for a weekend of scheduled normalcy. This is the first time since I arrived that a direct voice has disrupted that illusion. Like much of this country, Louisville is grappling with issues far more important than parties and horse races; struggling to find space for both is uncomfortable.

“I hope you’re right,” Rupp says.

She was. Despite tensions, the protests stayed peaceful. In Louisville 2020, these demonstrations are far more normal than seersuckers and mint juleps. They’re the reality that will not be canceled.  

Masks became part of many outfits | Horsephotos / Contributor/Getty Images

Half an hour before post time for the 146th Kentucky Derby, I walk into Jeff Ruby’s, the legendary Louisville steakhouse that’s a perpetual horseman hangout. I’m praying I’ll find a seat in the era of reduced capacity. But there are only three other people inside, six if you count singer Robbie Bartlett and her band.

Even the horses at this year’s Kentucky Derby were on edge. Before the race, one of Bob Baffert’s two horses lost control, bucking wildly in the paddock, and was scratched. His other horse, Authentic, held off Tiz the Law to win the Kentucky Derby. After the race, the horse Baffert described as “nice” tried to trample him in the winner’s circle.

“It’ll pick up once all the jockeys and trainers get done at the race,” Julie Howell, a VP with the Louisville Sports Commission, tells me as we sip bourbons at the bar. She’s not wrong: Around 9pm, jockeys begin to stroll in with their wives. Just before 11pm, Bob Baffert walks through the door. As I’m about to step up and congratulate him, Kay the bartender leans over the bar.

“It’s last call,” she said. “Do you want anything else?”

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