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Louisville is a typical mid-size American city ... then the Kentucky Derby happens

What it’s like to live in Louisville for two weeks before one of the biggest parties in the world.

Fifty weeks a year, Louisville, Kentucky behaves like a normal mid-sized American city. There’s a Triple-A baseball team and a minor league soccer team. There’s an airport that seems clean and spacious if you’ve ever spent a decade flying out of LaGuardia. There’s a thriving arts scene anchored by a nationally-renowned theater company, a symphony, an opera, and a ballet. People live and work here in businesses that have nothing to do with bourbon or baseball bats or thoroughbreds.

Then, in early April, right as the flowering trees bloom and the weather finally warms up, the city loses its damn mind. Work stops. Schedules have to be rearranged. The daily rhythms of a city that might otherwise be mistaken for Omaha, Milwaukee, or Raleigh are upended, and everything bows to the Kentucky Derby. It’s a legitimate holiday season, except that it exists only here.

The first sign that Derby season is upon you might be a fighter jet buzzing your office. Plenty of towns have air shows; few towns have air shows in preparation for a horse race. No town has a fireworks show on this scale for any reason. Thunder Over Louisville is the largest fireworks display in North America, drawing an estimated 650,000 people to the downtown waterfront to kick off the Kentucky Derby Festival two weeks before the race. (This year, it was held three weeks before so that it didn’t overshadow Easter.) Then there’s a marathon, a steamboat race, a hot-air balloon race, a massive parade, a waterfront concert series, and countless parties and galas … all for one two-minute race.

Or two minutes plus nearly 20 minutes of video review, as the case may have it.

From the moment the weeks-long Kentucky Derby Festival kicks off through the final sweeping-up of the shattered Mint Julep glasses, it’s a mad season for the entire city. The event supports a vast array of cottage industries — both year-round legitimate businesses and clever off-the-books race week side hustles. As one entrepreneur remarked after the Saturday’s 145th edition of the race, “I make money no matter what happens.”

And if you’ve got something planned that doesn’t get done by mid-April, you’re looking at two magic words: After Derby.

In the weeks leading up to the race, I spoke to some of the many people who work to make the season memorable.

I. Fashioning the Derby

The unique and flamboyant fashion of race attendees is one of the most visible traditions of the Derby. Bright colors, flashy suits, and stunning dresses are de rigueur at the track. And of course, nothing’s complete without the iconic elaborate hats — hats that have to come from somewhere. Several years ago, milliners Rachel Bell and Kate Welsh Smith saw a year-round opportunity and launched The Hat Girls, a brick-and-mortar store selling nothing but women’s hats for the Derby.

“98 percent of our revenue comes from the Derby events,” Bell says, “while the other 2 percent comes from bridal and miscellaneous hats.”

They sell hundreds of hats a season with price tags averaging $400, and often climbing well over a thousand.

“From June to December, we strive for a typical 40-hour work week in the shop. In December we begin ordering our supplies, making inventory plans for local boutiques, and looking for any upcoming color and design trends. From February to May, we work anywhere from 70-100 hours a week and in the final weeks leading up to Derby, we will work as many as 130 hours a week,” Bell says. “We’re in our hat studio 20-22 hours a day, frantically finishing up last-minute custom orders and helping out customers who may have just found out they are attending the Derby. Some customers will commission us for three hats — Thursday, Friday, Saturday at the races. It’s a complete madhouse.

“We have a bed in the back of our studio, so naps and sleep happen sporadically — but not very often.”

Hat secured, if you’re planning on being part of the throng that descends on Churchill Downs on the first Saturday in May — in 2018, over 157,000 people crammed into the historic venue, despite nearly three inches of rain on race day — you’re going to need a ticket. Louisville has you covered there, too.

II. Bringing in the crowds

For the last 20 years, Doug Dearen has run DerbyBox, a ticket brokerage whose sole focus is the race. As with the milliners, serving this need is a year-round business.

“It’s our niche — when we started this business, we made the decision to focus on the Derby exclusively. We’re a broker — if people ask, we can provide other events — if Carrie Underwood plays the KFC Yum! Center, we can get you in, but that’s probably 0.5 percent of our business. The rest is Derby week events.”

With so much focus on one event, this time of year is an end run to rival the race itself.

Fireworks during the Kentucky Derby Festival’s Thunder Over Louisville in 2012
Getty Images

“I don’t go on spring break, I don’t go to the dentist, I’m not getting a haircut — I’m Derby 24 hours a day,” Dearen says. “I can sleep next week, but we work all year for this week, to make sure everyone’s flight gets in on time, everyone’s checked into their hotel, and everyone gets their tickets. It’s a bucket list thing: people want to go to the Kentucky Derby. In the last ten years, it’s been more repeat customers — people love it, and they want to come back.”

III. Staffing up

To handle the outsized crowd that descends upon Churchill Downs for the Derby, outside reinforcements are needed.

“To employ people full-time at that track, you figure you might be serving ten thousand people a day on a normal day, outside of Derby week,” restaurant manager Alan Meyer, a veteran of multiple years behind Churchill Downs’ high-end bars, says. “On Saturday, it might reach 170,000. How do you service that many people well? It’s an expansive workforce they hire in — and they do a good job of it. They train up hundreds of people to wait on that crowd, so people don’t have to wait two hours to buy a drink. They’ve brought in mixologists from some of the top bars in the country to train people who have no bartending experience.”

There are bars spread all over Churchill Downs, from the relatively inexpensive general-admission areas of the infield and paddock, to the pricier box seats and terraces, all the way up to the exclusive Millionaire’s Row on the sixth floor of the massive venue.

“These are the professional athletes, 50,000 dollars a table,” Meyer notes. “In the [fourth floor] Stakes Room, I tended bar for four hours — balls to the wall — and I made over a thousand dollars. You’re getting paid hourly there; these tables are pre-paid, you can’t count on people who don’t have to pull out their wallet to remember to tip. You can’t put a tip jar up. But if people tip you, you’re gonna take it. I just had a box full of cash underneath my feet.”

The highest level of the Derby’s many tiers — both physically and spiritually — is one few people will ever glimpse. In 2014, the track’s owners vacated what was once the press box — moving media down to a first-floor office space that resembles a casino sportsbook — and turned it into “the Mansion,” an invitation-only space for the richest of the rich.

“It’s the most exclusive area in all of sports,” says special-event bartender Nicholas Doblick, who travels in from New York City each year to work in this gilded venue. “I manage two wine bars owned by the [James Beard Award-winning] celebrity chef Tony Mantuano at the U.S. Open Tennis tournament. His [Michelin-starred] restaurant Spiaggia is part of the restaurant company that oversees concessions at the Billie Jean King tennis ground and Churchill Downs. They don’t want to have bartenders gawking at the celebrities and media moguls, so they ship us in from New York for a higher level of service — we deal with that crap on a regular basis.”

There’s no signage pointing one to The Mansion, no advertising. “Even a lot of the year-round staff at Churchill don’t know about it, and they’d be fired if they stepped foot in it. My boss has never even been in that space.”

What differentiates a bar like this from the many lesser ones spread throughout the venue?

“It’s all level of service. One year, I had the CEO of Knob Creek come in — we don’t have that contract for our inventory. I sent my friend Michael out to find a bottle of Knob, anywhere. He came back with one in like ten minutes — blew me away. I still don’t know where he got it, but we were able to make the dude’s day. My first Derby, we had two bros try to test our level of service, and ask for Chick-fil-A popcorn chicken. Mind you, we have Top Chef winners making staggering food for these guests at all times. But we sent a girl out into Louisville — Derby day traffic and all — and she completely thrilled them.”

“We don’t say ‘no’ here.”

IV. The hidden city

Across the infield from the towering spectator structures and those millionaire bars, there’s a busy, sprawling, bustling place that few spectators will see or consider. The “backside” is the working end of the track, and it’s practically a small city unto itself. Rows and rows of stables, some fancier than others (I found myself wondering which one belonged to legendary horse trainer Bob Baffert, until I came across the only one that had four officers from the Jefferson County Sheriff guarding the door) are interspersed with living quarters, offices, a restaurant, a church, and a school for equestrian workers and their families. Children’s bikes and barbecue grills sit out, while chickens roam the grounds. At one point, a woman passed by on horseback, eating a slice of pizza as she rode.

“This is the thick of the shit here,” one trainer laughed, two days before the Derby, “and if it’s this crazy today, tomorrow’s gonna be hell!”

The backside is a different world from the glittering party across the way, but it has a better view of the track than any five-figure seat on the frontside. Here, it’s families at picnic tables and camp chairs, cooking out under the shade of trees, capping the season with parties for the people who worked all year to train and care for the horses — the people who make the Derby happen.

V. The invisible hand

Back frontside, it’s not just drink that fuels the Derby. An army moves on its belly, and those tens of thousands of people need to eat.

Food capacity doesn’t scale up for a big crowd as easily as mint juleps and bourbons, so Churchill Downs is realistic. Unlike most sports venues, you’re allowed to bring your own food during Derby Week. This small leniency begat another of the many cottage industries that spring up around Louisville because of the races: high-end box lunches. Restaurants all over town take catering orders weeks in advance and prepare portable meals for race-goers.

“Everything has to be packaged up special for the Derby — clear plastic bags of a certain size,” says Kelly Schack, co-owner of The Block Gourmet Deli, a restaurant on Louisville’s East End. “We stay away from mayonnaise-based things, chicken salads — anything that needs [to be] refrigerated, when you’re going to be out in the heat with this all day.

“When you’re bringing an extra hundred or two hundred thousand people into town this week, it helps generate a lot of revenue for mom-and-pop businesses like us.”

Derby also generates revenue for people who are willing to hustle and get a bit creative. Parking is tight around the Downs, which sits smack in the middle of a dense old neighborhood. Starting on Thursday, Steve Jones stood on the side of a residential stretch of South 3rd Street wearing a construction company’s yellow safety vest and a handwritten sign advertising parking for $20 a car.

“Double back and drive down the sidewalk!” he told me. He nimbly and expertly directed my car between two oak trees and a pickup truck to park in the remaining seven feet of what was — I hoped — his front lawn. “C’mon, gun it!” he bellowed, as I hung up on a large tree root. “That’s a Ford, right? You can make it. Oh, it’s a Honda? Alright, well, be careful.”

After finally squeezing me into the improbably small space, he expounded on his business: “I bought this house 25 years ago for $15,000,” Jones says, “and this is just free money each year. I man the whole block, and I’ve got more spots in the alley out back.” He then pivoted to other business interests, selling me a poncho right as it began to rain.

Entrepreneurs like him line Central Avenue, seeking new markets to fill Derby-goers’ specific needs, whether that’s bottled water, homemade barbecue, or a dry t-shirt. Forgot a hat? There’s a woman selling them from the hood of her car. Leaving barefoot because high heels sting after ten hours at the track? There are men selling flip-flops for the walk home.

VI. Madness takes over

As race day approaches, you can feel Louisville’s attention span wane, and the latent spirit of native son Hunter S. Thompson bubbles up through the seemingly-normal people all over town.

Jefferson County Public Schools and the University of Louisville’s schedules bend around the Derby. I have two young children in daycare; both of their schools’ schedules were truncated starting Wednesday, to accommodate parade routes, Derby parties, and staff heading to the track. Offices turn into ghost towns by mid-week, as entire departments head out en masse to join the celebrations. Deadlines are pushed, race day given the kind of wide berth given to Christmas in most places. A neighbor’s middle-grade children attend a fancy, expensive local private school, and the school holds an optional 48-hour lock-in so parents can drop their kids off for an entire weekend at the track.

“If you grew up in Louisville, if you went to college here, you’ve got a bad Derby story,” says Joe Kelly, a local ESPN radio host and barbecue chef who’s spent many years attending and now covering the race. “I’ve got stories I can’t share. If you’re in Louisville and you’re having brain surgery, just know that your surgeon’s probably had a bad Derby once.”

The weather almost always finds a way to color the Derby experience, as it did Saturday when a long, chilly afternoon of steady rain turned the track and much of the grounds into a sloppy mess.

“I think there’s been four legitimately nice weather days in my 37 years alive,” Kelly says, “but people who party for Derby, they’re like the U.S. Postal Service. They’re here rain, sleet, snow, whatever, it’s not stopping them.”

The festivities extend far outside Churchill Downs. Louisville is already on the far end of the drinking permissiveness spectrum: by law, bars are only required to close between 4am and 6am year-round. But during Derby, even this provision isn’t enforced. Some bars will stay open for 72 hours straight, from Thursday through Sunday morning. “Back when I was bartending, I worked 48 hours straight one year,” Kelly recalls.

Horses walk by a sign stopping traffic during morning workouts at Churchill Downs in 2002.
AFP/Getty Images

One young National Guardsman standing watch on the backside Friday morning viewed the crowds with bemusement and wonder. “I’ve been doing this a couple years, and we see everyone coming in, they’re looking prim and proper and nice — these are obviously people with money — and then eight hours later, you see the same people on the way out, their knees and elbows are bloody, they’re covered in mud, starting fights or falling over trying to.” He gestures to his boots. “These are jungle boots, and I’m glad — it’s always a mess out here.”

The “Kentucky Derby” is much more than one two-minute race; Derby Week racing begins Tuesday, and builds throughout the week. Friday’s Kentucky Oaks draws a crowd of 100,000-plus, an amazing number for an event that will get little if any coverage outside of Louisville. Many locals, though, opt to leave the Oaks and Derby both for the tourist crowd and attend Churchill Downs on Thursday, a day that has become known (first unofficially, now officially) as Thurby, drawing crowds around 50,000 in recent years.

“This is the best, for me,” says Dan Hoffman, a Louisville native watching from the boxes on Thursday. “Everyone’s dressed up, you’ve got all the energy of Derby, but you can still breathe.”

VII. A year in two minutes

The Kentucky Derby bills itself as “The Greatest Two Minutes In Sports,” but for many, the actual running of the race at 6:50 p.m. Eastern on the first Saturday in May is only the culmination of a whole season — a massive undertaking that impacts every aspect of life in a city this size. I lived in New York City when it hosted Super Bowl XLVIII, and it barely registered as a blip on the city’s radar. This? It’s like hosting three Super Bowls over a long weekend in a city somewhere between Hartford and Richmond in size, and doing it every single year.

Seeing Churchill Downs packed to capacity, I understand why so many people I spoke to for this piece used the term “bucket list.” From the infield to the trackside bleachers to the box seats and suites above, every inch of the historic complex swells with people decked out in their most ostentatious outfits, people-watching of the highest order.

When the moment finally arrives, it’s something to behold. Just before post time, the band strikes up the possibly-problematic-but-utterly-beautiful state song, “My Old Kentucky Home,” and hundreds of thousands join in singing.

“For me, it’s very emotional,” Dearen, the ticket broker, reflects. “When those horses come out on the race track, I need to be by myself. We work to this all year, and I just need to go somewhere I can put my head in my hands, say a prayer and cry. People ask me, ‘Do you really cry at the Kentucky Derby?’

“If you don’t cry at the Kentucky Derby, you don’t have a pulse.”