Derby Confidential

Nudity is a virtual rite in the Churchill Downs infield during the Kentucky Derby — flashers atop their boyfriends' shoulders, drunks shucking their clothes after a day of mud and sweat, and the general havers of good times who incorrectly think the thousands of cops on the scene will turn a blind eye to their naughtiness. That's the infield, in a nutshell.

But eight hours after the big race, a man would sit stark naked on a Highlands barstool, casually gulping a drink while alarmed and amused bar patrons milled around him.

This event became an annual Derby tradition, not unlike drinking mint juleps and donning of gaudy hats, says a former longtime bartender at Cahoots on Bardstown Road.

 “It got to the point that people would show up on Derby at 4 a.m. just to watch this guy,” said the former drinkslinger. “And he would just take off all his clothes and sit at the bar, like there is nothing abnormal going on.”

Each year, the Derby transforms a usually well-mannered city into mangled messes of revelry. The bars and restaurants that 51 weeks a year are the scenes of restrained liveliness become rowdy, noisy, overflowing parties, and the hotspots that are usually rowdy become out-and-out madhouses. For a few days, Louisville's swinging districts become Cancun at the height of spring break.

And the bartenders, waitstaff and limo drivers who count this week as their busiest — and most lucrative — time of the year see it all. They witness and hear every bit of depravity by the revelers, but are mostly ignored until the glasses empty or the plates begin to stack up.

These good-time enablers were willing to share their experiences of Derbytime debauchery, but only on the condition that they go unnamed, so as to not endanger their livelihoods.

For celebrating patrons, “the whole ‘give a damn' goes out the window,” said a veteran server whose employers have included Seviche and Jack Fry's. “There's a whole new list of rules that you just have to deal with.”

A few years ago, a man joined his party quite late on Oaks night and couldn't understand why his order didn't arrive with the rest of his tablemates' dinner. The result was a series of shouts, furiously waved hands and finger snaps at the already besieged Seviche waiter.

Meanwhile, the Bardstown Road restaurant had filled to capacity and a line had developed outside the restaurant.

“I just wanted to throw my hands up and be like, ‘Do you not see what's happening here?'” our server recalled.

The Derby madness builds up to Derby Eve — the crowds are usually too wasted from all-day partying on Derby Day to wreak much havoc. While the Thursday before Derby is also busy, the real madness starts at about 8 p.m. on Friday.

“It's like someone opened a floodgate,” the server said.

“The worst night is always Friday night,” said a bartender at a swank downtown hotel restaurant. “They're getting their party on for the first time. They're not completely exhausted and tired — they're kind of like kittens on Derby night.”

Celebrities wander in and out, although they mostly spend their time in the roped-off V.I.P. sections of parties instead of the open bar in a public restaurant, even if they plan to ostensibly sleep off the parties upstairs.

This hotel, like most during the Derby, is particularly pricey; the restaurant isn't cheap, either. Because of this, the crowds aren't likely to bust windows or urinate into planters. They're often people steeped in the thoroughbred industry — “Derby professionals,” the bartender calls them.

At most, they're just really loud — uncharacteristically loud for this venue.

“There isn't fighting or anything,” the bartender said. “Well … it has happened before, but it doesn't happen much.”

This bartender finds herself pouring much more bourbon than usual and mixing many more mint juleps, of course. And the partiers can be flirty — she has had a few flirts try to work their magic, as have colleagues — but they're generally in good spirits, to the point that a bartender can be feisty, too.

“It's fun because you can make fun of people on Derby,” the bartender said. “They're not as defensive. Everyone's just trying to have a good time.”

Derby Day for a limo driver is less hectic, mostly a lot of waiting around as clients watch the race, go out for dinner and then head out for a night of drinking.

Their charges are usually behaved, says one limo driver with 10 years behind the wheel. Usually. Sometimes, a hard partier won't be able to contain the massive intake of liquor he's consumed and vomit inside the car, which most self-respecting limo drivers strive to keep tidy.

“We'll have to clean it up (but) they have to pay extra for that,” he said. “Usually, on Oaks night, a lot of them will start drinking before noon. At night, they're in good spirits.”

(Oddly enough, he says his passengers rarely close the partition between the front and back seats. But when they do, he reminds them to clean up whatever substances, er, might get spilled.)

Big-time celebrities usually hire out police escorts to get around during Derby, the driver said, so his Derby clients are usually businessmen and racing industry types. (His most famous passenger was weight-loss tycoon Jenny Craig, a prominent dabbler in thoroughbreds.) They tend to be nice — especially at the end of the day, when they'll offer tips ranging from $300 to $1,500. But it's not necessarily easy money.

“About 5 percent are arrogant and talk badly to you,” the limo driver said. “They talk to you like you don't know where you're going — in your own city! They think they know a quicker way to go. Their attitude is that they're paying you and they can tell you which way to go.”

(In these cases, he says he'll simply note that he has to drive certain roads that are safest for his large vehicle.)

The veteran restaurant server says the good times have no limits. A few years ago, a prominently controversial ex-jock approached him and a co-worker and asked if they knew where he could find marijuana. And then he asked for cocaine.

This server has also watched in awe as fistfights broke out, akin to the viral YouTube videos of slugfests in fast-food restaurants. But these brawls weren't happening at McDonald's — they were happening at Jack Fry's.

“It's like, this is a fine-dining restaurant,” he said.

For food-service workers, this is the wildest, most stressful and occasionally humiliating time of the year. So why do they keep  subjecting themselves to this?

The tips, of course.

For starters, Derby Week is, if anything, an excuse to splurge.

“People really let loose — $5,000 bottles of wine, $6,000 bills for a table of six,” the server said.

And the patrons can be astonishingly generous — especially after a good day at the track. Big winners have been known to leave $100 tips for a few drinks, said one of the bartenders.

That's not a rule, though. In fact, there are no rules. A veteran server might be able to predict which patrons will open their wallets at the end of the night, but not during the Derby.

“You'll have customers who are really demanding and rude, but, amazingly, they leave a great tip,” the server said. But then there are diners who seem friendly and easygoing, only to leave a penurious tip.

Europeans tend to fall into that category, he said — they're known for leaving a 4 percent tip on a $600 check.

“They have a totally different system for gratuity, and they don't necessarily follow the ‘when in Rome' thing,” he said.

How ironic.

“You never know what you're going to get,” he said.

That's true for everything during the Derby, after dark.