Jamie Reidy explains why you HAVE TO spend the first Saturday in May in Louisville: The Kentucky Derby.
Only one thing can stop me from attending the next twenty Kentucky Derbies: my sister.
Anne-Marie, I love you. And I really, really want you to fall head over heels with a wonderful man and get married someday. But, I beseech you: please do not choose the first Saturday in May for your wedding.
There are 364 other days on which to get betrothed. Pick one of them, so I can make my annual pilgrimage to Churchill Downs, where I will scream and jump as the thoroughbreds come down the backstretch in The Greatest Two Minutes in Sports.
I wasn’t always like this. When I boarded a plane to Cabo San Lucas for my friend Tim’s bachelor party in April 2004, I had no inkling that I would soon be going to Louisville every year. But that’s the monster Boyd created.
The best man and trip organizer, Boyd grew up in Louisville and attended the University of Kentucky with the groom. In classic guy fashion, it took me twelve hours to realize Boyd wasn’t his first name, but his last. (Note: I’ve only heard his wife, parents and brother call him “John.”)
A Louisville resident, Boyd could not contain his excitement for the upcoming “Run for The Roses,” just a month away. He regaled the bachelor party attendees with Derby stories, displaying the fervor of a born-again Christian still dripping from his baptism.
“Reidy,” he said, only it sounded like Rady, “You should come to Derby this year. Stay with me and my wahf Heather.”
I raised a dubious eyebrow. “Dude, I’m the kind of guy who will actually show up! So, don’t invite me unless you’re ready for a pale, bald guy who talks a lot to knock on your door.”
Boyd stared at me as though I’d just declared that Kentucky grass was not, in fact, blue. “That’s why I invited you.” He poked a finger into my chest. “You’re coming with us next month!”
I immediately told Boyd I was free. (One of the many advantages to being hopelessly single is that I don’t have to check my schedule to see if I already have plans on a given weekend.) He assured me that I’d be staying with him and his wife. I didn’t give the plan much thought; we were already muchos margaritas into the dia, and guys always make promises that get quickly overturned once their spouses learn of them. But at the end of the weekend, Boyd told me, “See you in three weeks!” He sounded serious.
It’s cheaper to fly from Buffalo to the Bahamas in February than it is to get into Louisville for the first week of May on less than twenty-one days’ notice. Sadly, I simply could not afford the trip. So I got work to pay for it.
Six months earlier, Eli Lilly’s Oncology division had made the mistake of promoting me to “sales trainer.” My territory ranged from Cleveland to Seattle. Basically, I spent all my time flying around to work with new reps or poorly performing veterans, hopefully improving their sales techniques. Twice per fiscal quarter, though, my boss required me to ride along with “superstar” reps, from whom I could glean tips to later be shared with the rookies and deadbeats.
Conveniently, the women who comprised the greatest sales duo in the history of Lilly Oncology were friends of mine… and just happened to reside in Louisville.
The nice lady at the Eli Lilly travel agency managed to get me a corporate discount on the airfare, but finding a room within 100- furloughs of city limits proved much more difficult. During the 45-minutes we spent on the phone, she grew more and more frustrated as every hotel chain was either booked or ridiculously overpriced. “Even The Clarion is $300!” she groaned. “They must be having a conference in town or something.” I nodded in silent agreement. Or the world’s biggest horserace.
My betting on a long shot at the 2004 Kentucky Derby looked like a long shot. There was no way I could stare my boss in the eye and tell him that it was absolutely necessary that I spend the last three days of April with the Louisville reps at five times the cost of a normal trip.
“Here’s one!” The travel agent’s excitement singed the phone line. “The room’s only $115 a night.” I rolled my eyes. “Is it in Kentucky?”
She assured me it was in downtown Louisville.
She assured me it was a quality establishment. We booked it.
Boyd cracked up when he heard where I was staying. “You gotta be kidding me!”
Did you know that some hospitals have a hotel on the grounds, in order to provide reasonably priced housing for patients’ families? I did not. But I learned all about it when I checked into Jewish Children’s Hospital.
Turns out that Derby City hops for the entire week prior to the big race; hardly anybody works. That is, except for “The Lisa’s,” the superstar reps who got stuck with a jackass trainer on Wednesday and Thursday. Between sales calls with Lisa F., I learned that if I wanted to continue embarrassing myself among manly men, I should stop calling cement mixers “cement mixers.” People in the know refer to these vehicles as cement “trucks.” (Lisa sold cement in a previous gig.) Eight years later, I am still waiting to impress somebody with my lingo.
Prior to my departure for Kentucky’s largest city, I called Boyd. “Make sure you bring a suit for The Derby,” he told me.
Good advice, since I hadn’t given much thought to my race attire. I’d forgotten all about the tradition at southern colleges by which everybody gets dressed up so they can then go spill bourbon on themselves prior to football games. Even though I had a nice tan suit that would have gotten the job done, I decided to survey a few born and raised belles, just to be sure.
Their response was unanimous: seersucker. My mind filled with images of Jay Gatsby, I went shopping on line.
Jos. A. Bank offered the least expensive seersucker suit I found. At $225, it looked like a deal breaker. Since the pharmaceutical industry was one of the last to require strict business dress, I already owned eight suits. The thought of buying another didn’t excite me, especially one that I’d wear just once.
I shared these concerns with a southern redhead with whom I’d been spending some quality time. She assured me those would be two hundred and twenty five of the best dollars I’d ever spent. Still I wavered. When she requested a private fashion show, I decided to follow her advice. I picked white seersucker with light blue stripes. (I drew the line, however, at buying white bucks.)
Boyd informed me that we did not have tickets to the Derby; we were going to the Kentucky Oaks, a day of races on Friday. He explained that Oaks was actually more fun because it attracted more locals, whereas Derby drew “amateurs”. Shee-it. I would’ve gotten a Rebel flag tattoo – fear of needles, be damned! – if Boyd had told me all the locals had one.
By the time Friday rolled around, I had already fallen in love with Muhammad Ali’s hometown. What hospitality! Never before had I encountered a city that so completely embraces an event the way in which Looavul revels in the Kentucky Derby. It was as though every citizen had been deputized an ambassador intent on making sure my visit went as well as possible.
On Kentucky Oaks morning I nervously buttoned my new seersucker jacket (white buttoned down shirt and blue and gold striped Notre Dame tie) and looked in the mirror. I dunno. This could go either way… big hit or big laugh.
I walked out of the guest bedroom haltingly, like a teenaged girl in her first prom dress. I held my breath. But Boyd’s delightful wife Heather let out a whistle and I knew everything was going to be all right.
And then Boyd handed me a bourbon and water on the rocks.
Eight years earlier, I had dumped the first bourbon a Louisville native handed me. But, thanks to So Cal beach residents Tim The Groom, his henchmen Patrick and Steve and their frat-like peer pressure to pound Jack and Cokes, I’d become a dark booze guy. Still, 9:00 AM is awful early for the hard stuff.
But I couldn’t disappoint my host. After a big exhale, I took a sip.
Who knew bourbon and water tastes so good in the morning?! The key, I learned, is good booze. Woodford Reserve, to be exact. Yum.
The good times continued rolling as we neared Churchill Downs.
Women pointed at me. Stared. Smiled. Flirted. And these were just the ladies on whose front lawn we parked for $15.
I hesitated just outside of security. The dozens of State Troopers waited, eager to make a bust. Boyd winked and urged me forward.
The officers quickly patted us down and found nothing. Boyd and I sailed through the metal detectors, which failed to, uh, detect the plastic flasks filled with bourbon nestled in the small of our backs like concealed weapons.
Boyd and Heather headed for the seats while I hit the bathroom. Then I bought a beer and went to join them, which is when things took a surprise turn. An enormous, ancient black man selling beer boomed, “That’s a mighty fine suit!” I stopped and looked around, trying to identify the target of his compliment.
“I’m talkin’ to you, son,” he pointed at me with a finger the size of a Devil Dog. His other hand engulfed a Coors Light can, making it look like a silver bullet Pez Dispenser. Instantly, I felt embarrassed, figuring this guy was clearly trying to butter me up to buy a beer from him. I sheepishly raised my hand, which already held a Bud Light. He scoffed and waved his hands down at me.
“I don’ care about dat. If I had my camera, I’d take a picture and bring it home to my wife, and show her what a fine suit that is.” I thanked the nice man and walked away with even more spring in my step than before. With the old guy vote in hand, surely the ladies would soon follow.
I had no idea.
Southern women instinctively reach for seersucker the way Italians reach for bread – like it’s encoded in their DNA. No belle can resist rubbing the crinkled cloth between her fingers, even if it’s draped on a stranger and her boyfriend is standing nearby. A seersucker suit is the fashion version of a Jedi mind trick – “I am the droid you are looking for.”
I won’t bore you with the statistics on how many attractive, female strangers smiled coyly at me while rubbing manicured fingers against my white and blue striped upper body. Suffice to say the Axe body wash commercials are based on my experiences and a lawsuit has been filed.
I called my parents and exclaimed, “I feel like Justin Timberlake!” Cricket, cricket. “Uh…I feel like the Beatles!” Mom and Dad cheered.
As did more women. I’m talking gorgeous, perfumed women in sundresses. And if you like southern accents? Suh… you will tip your cap to Churchill Downs on Derby weekend.
Speaking of which, I haven’t even covered the hats. Holy headgear! It’s easy to tell which female passengers on your connecting flight – no commercial airlines fly direct to Louisville from the coasts – are going to the Derby: the ones with hat boxes in their overhead bins. Jockey-less horses are a more common sight than hatless ladies. I’m not talking bitty bonnets, here. At The Derby size matters and the bigger the better.
For me, a hat is a hindrance; it’s tough to tell if a woman is attractive or not when a veil, or a bouquet or a floppy brim covers half her face. But this is simply another area of fashion where a man’s opinion matters none; ladies pick XXL hats to impress other XX-chromosome holders. It is, I gotta admit, a lot of fun to watch two women with sombreros atop their heads try to elegantly pass one another in the corridor without knocking brims – like two aircraft carriers trying to fit through the Panama Canal simultaneously.
Whereas the Infield displays every negative Southern stereotype, the Grandstand parades every positive one. Walking amongst the shaded box seats is like stepping back in time to an era of Southern aristocracy and elegance, chivalry and courtesy, grandeur and tradition – only with Ray Bans, Rolexes and Razrs.
Another tradition still in full bloom: betting. I utilize the same philosophy at the racetrack as I do when playing Craps at a casino – I do whatever the person I’m with does. This “strategy” has never paid off at the tables and it didn’t do me much good near the stables, either. But, wagering only $2 or $4 per race wasn’t going to break me.
Boyd, Heather and I sat in a 3rd floor clubhouse box, a very nice location to watch the races made nicer by its immediate proximity to two attractive women in their mid-twenties. Before the 9th race, one of the women, “Katie” (names have been changed to protect my chances of getting great tickets to future Derbies), nodded to me and said, “Nice suit.” Game on.
I quickly struck up a conversation with Katie, but my eyes targeted her friend “Melissa.” An hour later, Melissa received a brief call on her cell phone. Hanging up, she turned to Katie and nodded. I felt like I was witnessing confirmation of an assassination attempt.
The call had come from a 5th floor suite, a.k.a. where the horse trainers hang out. One of the unique attributes of horse racing that turns Pete Rose green with envy is the fact that all the participants (owners, trainers and jockeys) can – and do – bet on the races. Consequently, people who know people are always receiving tips. Apparently, Melissa’s father ran with the cool crowd.
She asked if I wanted to walk with her to place a bet on The Kentucky Oaks race. A sillier question had not been asked of me since a girl in high school wondered if I wanted “to go for a walk” at a keg party. I tried not to jump down the stairs to the betting windows.
Melissa instructed me to place a “trifecta box” bet on the #1, #3, and #6 horses. My blank, but hopeful stare prompted her to explain that I would collect if those three horses won, placed, or showed – regardless of their order. Her gambling know-how prompted a party in my pants.
Desperate to impress her, I upped my wager to $10. The bet-taker waited patiently for a few seconds, then coughed in exasperation. “Sir, a trifecta box is six bets” – (under a scenario of each horse winning, there are two other potential outcomes, i.e. one horse comes in second and vice versa. 1,3,6; 1,6,3; 6,3,1; 6,1,3; 3,1,6; 3,6,1) – “So you owe us sixty dollars!” I tried not to loosen my now sweaty shirt collar. Shaking with shame, I handed over the cash as skillfully as Woody Allen snorted cocaine in “Annie Hall.”
Without looking to see if my betting Belle had witnessed my embarrassing performance, I sprinted to the Mint Julep guy and bought us another round. Melissa smiled and walked upstairs ahead of me. I pressed the icy glass to my face.
The Oaks distinguishes itself from other races by featuring only fillies. The 1 and 6 horses immediately bolted way out front and stayed there. That 3 horse, though…she tried her best to make me cry. I nearly lost my voice screaming, “Come on, Thee Horse! Come on, Three Horse!” Finally, she obeyed, pulling away from the fourth place finisher down the backstretch.
We hit the trifecta! People speak The Truth when they say nothing in sports is more fun than cheering your horse down the backstretch of a race.
“Reidy!” Boyd yelled at me. “Do you have any idea how much you just won?” In all the excitement, I’d forgotten about the money. Math was never a strong suit of mine. I guessed, “A couple of hundred?” Before Boyd could slug me, the official results appeared on the Big Board. I’d won $2500. Commence hugging.
When a woman wins you a coupla grand, it really gets a relationship off to a flying start. I asked Melissa for a date that night and she agreed. We got along famously.
The next morning, Boyd, Heather and I struggled with our hangovers on the couches. We all agreed that we were psyched we didn’t have tickets to the Derby, as it’d be such a hassle to get all dressed up again, battle traffic, find parking, etc. Thankfully, we were only going to their friends’ annual party to watch on TV. Then my cell phone rang.
Melissa was calling from the police-escorted bus her father rents to chauffer friends and clients to the Derby. Daddy had four box seats along the first-turn rail left over. Gratis. Did we want them?
Not wanting to impose my will on my hospitable hosts, I turned to Boyd for a decision. Boyd turned to Heather and said, “Find a hat.”
Talking while on line for the betting windows, Boyd and I figured out that my mother and his father have the same birthday, April 4th, 1944: 4/4/44. Instantly, we decided Divine Intervention had brought us to the track that day for the sole purpose of betting on the #4 horse in the Kentucky Derby. I wagered $44 to win. The woman behind the glass – thankfully not the bet-taker from the day before – tilted her head just enough to let me know I was an idiot. I called my mom and told her she had to watch the race and cheer on “Action This Day.”
And then the heavens showed us blasphemers what true divine intervention looks and feels like, unleashing a storm of Biblical proportions. Box seats on the rail are great…until lightning flashes. Boyd, Heather and I got soaked beyond salvage as we splashed through puddles to shelter. I worried Heather might have a breakdown, but she quickly alleviated my chauvinistic fears. “Hey…we’re still drinking. At The Derby. For free.” Cheers to that! (Note: Boyd hit the marital jackpot.) He took his better half’s enthusiasm to another level. “Trust me, Reidy. The sun will come out for The Derby.” I asked the bartender for one of whatever Boyd was drinking.
Two hours later, the rain ceased. Shortly thereafter, the clouds parted just enough for the sun to make an appearance. I was yapping away about something when Boyd punched my arm to shut up. Horns blared and more than 140,000 people grew solemn. “My Old Kentucky Home,” Boyd explained. I nodded, despite having no idea what that meant.
“My Old Kentucky Home” is the Kentucky state song. Sad, yet sweet, it reminds me of “I’ll be home for Christmas” in the singer’s wistful tone. (I have no idea if any Kentuckian agrees with me on that.) The only people who did not get misty during this song were those on their first or second trips to The Derby. The toughest men in Churchill Downs cried, and Boyd did, too. I wished that someday I would join them.
At the tune’s conclusion, the crowd roared in approval and anticipation – The Kentucky Derby would soon begin.
When the horses ran past our box along the first turn, the crescendo of their hooves shook the ground; quite an awe-inspiring moment. But once they passed, we had to shift our gaze to the giant scoreboard that broadcasts the race.
Surprisingly, Boyd and my algorithm did not produce a winner, as ATD finished in sixth place. But all was not lost. I had also bet $50 to win on a horse named Smarty Jones. Paid me $200.
I’ve only missed one Kentucky Derby since then, in 2010 for my friends Matt and Ashley Heyn’s wedding. I haven’t won $2700 again. But I have gotten a date at The Oaks (2008) and I have received free tickets to both The Oaks (thank you, PJ Mastracchio, for hooking me up in 2007) and The Derby (thank you, Darran Winslow, for being so hung over you couldn’t rally in 2008).
In 2008, I got a little misty for the first time during “My Old Kentucky Home;” not full on crying, but I got closer in 2011.
Of course, I still wear my seersucker every year, though my original suit had to be “put down” after suffering fatal injuries in a 2007 post-Derby freak accident with a guard rail dividing the four lanes on Commonwealth Avenue (no charges were filed in the alcohol-fueled incident, but the barrier in question leapt up without warning to trip me as I hurdled it like a gazelle). Like an owner who gives the replacement dog the same name as its predecessor, I purchased the exact replica seersucker from Jos. A. Bank. I still feel like Justin Timberlake when I stroll through the Grandstand at Churchill Downs – albeit an even older and balder version than I was in 2004.
And I still hope my sister falls in love and gets married someday. Just not on the first Saturday in May. Oooh. Maybe she’ll pick a date in spring or summer, though.
That way I can wear my seersucker.