Bets, Bourbon, Bluegrass and Hope at Keeneland

Horse racing gets dressed up and places a bet on itself at Keeneland.
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Brian Spencer sat at a table on a sun-dappled hillside overlooking Keeneland. He had a thin, light brown beard, a zip-up hoodie in blocky blue, green and white stripes, and similarly colored Dolce & Gabana sneakers, an outfit that stood out amid the thousands of other young men swarming the Lexington, Kentucky racetrack on the day of the Bluegrass Stakes.

The dirt road from the sprawling limestone racetrack complex to the “tailgating” site where the America’s Best Racing bus had put in was a maelstrom of linen, khaki, and seersucker, dotted with a smattering of Nantucket Reds. Young women clad in sundresses audibly questioned whether they should carry their high heels for the rest of their walk to the grandstand.

I was also a fashion outlier. Brian and I did at least have on khakis, tradition being tradition, but ours were substantially more rumpled than the crisp-pressed ones of the khaki-clad horde. Unlike me, he didn’t seem concerned about being underdressed. As part of America’s Best Racing’s initiative to generate new fans for the sport, he was there to dispense handicapping advice to his more sartorially inclined peers. The slow-moving, party-minded khaki snake was there because it was Kentucky, and because they wanted to be.

“I was a math kid,” Brian told me, when I asked him how he fell into the sport. “I grew up outside of Chicago, and my mom would take me to Arlington Park. Now I have the start of a career in it.”

Part of the career, for now, involved hitting the spring’s major races, like the Bluegrass Stakes, in which three-year old horses competed to qualify for the Kentucky Derby. It’s nice work if you can get it: his job is showing people how to read a program – the esoteric, finely printed collection of data outlining a horse’s past performances – in order to get an edge, or at least bet as if they knew what they were doing.

There were other parts to the publicity push, too. Before I made it to Spencer’s table, Hailey Hardy, one of six “brand ambassadors” traipsing around the country on the 45-foot long tour bus, had approached me with her left hand filled with a wad of two dollar betting vouchers.

“Do you want any?” she asked.

I politely declined. I was already sitting on a juicy voucher of my own – okay, $150 dollars – from her employers, the National Thoroughbred Racing Association. They had generously flown me down to Lexington and booked me in a convenient downtown hotel adjoined to University of Kentucky’s famous Rupp Arena. Brian and Hailey and I were all there for the same reasons, more or less: because NTRA thought our various presences might help the sport in various ways.

Although I might as well admit that I was also there for another, simpler reason: the opportunity to visit one of the temples of a sport that I love. With a scant three weeks of racing in the spring and another three in the fall, Keeneland relies on the laws of supply and demand – restrict one, watch the other spike – to fill its grandstands. At some point, though, Keeneland’s popularity is a tautology: the hordes come to Keeneland because it’s Keeneland. Brian and Hailey and I are hardly necessary.

Keeneland is in the heart of the Kentucky bluegrass, surrounded by prominent horse farms enclosed by whitewashed fences, the fairy-tale location amplifies the appeal. Every winter, when racing isn’t in session, the private jets of the oil-rich and well-inherited touch down at Bluegrass Airport, just across Versailles Road from Keeneland. They’re there to participate in the annual yearlings sale, and spend gargantuan sums of money on the most promising young thoroughbreds in the world.

I had landed in the sport in the same way as Spencer – a math kid from outside of Philly, it was my grandfather who took me to the track – and had been probably playing for longer, I wasn’t on his level as a handicapper. He told me that he liked to work by carefully observing the entire meet, watching replays of every race on every day, and judging trends from jockeys, trainers, and the track surface itself.

“Recently, I’ve become more of a visual handicapper,” he said, as Jerry Garcia and David Grisman’s rendition of Shady Grove tumbled out of an adjacent speaker into the Kentucky afternoon.


It seemed like everyone here was a better handicapper than me. Much earlier that morning, Katherine Wheeler, a Lexington-based employee of the NTRA, was leading me through the stables on the backstretch of the track while grooms led the horses back from their morning workouts. A vivacious brunette who had been working in various facets of the industry since graduating college four years earlier, Wheeler let it slip that she last year she had cashed a $3000-plus ticket by picking the winner of both the Kentucky Derby and the Kentucky Oaks, the big-ticket race for three-year-old fillies that precedes the Derby by a day.

“I thought I’d only made a two dollar bet, but then I checked my Twin Spires account, and when I saw my balance, I realized that I’d actually put it down for ten,” she said.

Here was a sum I’d dreamt about my whole gambling life, mentioned offhand. The whole visit was like this, not quite by accident. Outside the stables in the post-dawn chill, I met Rosie Napravnik, the 25-year old who has risen to become one of the top jockeys in the nation; she gave me a quick, hurried handshake, on her way to more important business. I met five-year old gelding Wise Dan, the 2012 horse of the year; he was more attentive, but he was also confined to his stall. Having won the $300,000 Maker’s 46 Mile the previous day, my higher-earning namesake did not have a workout lined up.

Norteno music played on a boombox, providing distraction for the Mexican grooms handling their morning tasks. Calls of “coming through” punctuated the air, as horses sporadically returned to the barns. In the distance, a siren sounded, indicating that a horse out on the track had broken free. No one seemed all that worried.


Six hours later, on the opposite side of the racetrack, Keeneland was all noise. The gradual filling of the clubhouse, grandstand, and apron in front of the track produced a steady din from the crowd that would not subside through the afternoon. It peaked, briefly, every half hour with the actual races.

Keeneland was in its second weekend of the spring meeting, and ultimately 37,161 racing fans would pass through the gates, likely the largest crowd of the year, in order to catch some or all of the day’s dozen races, which included the Bluegrass Stakes.

Thanks to a new, point-based system for qualifying for the Kentucky Derby – to be held three weeks later, 80 miles down the road at Louisville’s Churchill Downs – it looked like both the winner and the runner up in the Bluegrass Stakes would both be guaranteed spots among the 20 in the starting gate at the Run for the Roses. Never mind that only one Kentucky Derby winner had competed in the Bluegrass Stakes – Street Sense in 2007 – since the installation of a synthetic racing surface in 2006.

Well, some minded. Racing enthusiasts and turf writers grumbled when the Bluegrass was enshrined as one of the seven 100-point races when the new system was announced in 2012, mostly because performances notched on the Polytrack didn’t seem to translate to success on the dirt track at Churchill, or any dirt track, for that matter.

But from another perspective, one that considered the optics in a sport starved for positive press, the Polytrack couldn’t have been less important. It would, from the perspective of a sport looking to rebuild fan interest nearly from the ground up, have been asinine to devalue a race that had been run for over a century, at perhaps the most picturesque setting in the game, on a day that attracted a young, fashionable, and moneyed crowd. Whether the next Derby winner would win at Keeneland wasn’t the point; Keeneland and the Bluegrass Stakes were.

This is doubly easy to understand in contrast to the notably less-upscale Wood Memorial, another 100-point race that had been held the previous week at gritty Aqueduct Park in Queens. When there last year, I saw top three-year olds competing on perhaps more predictive dirt. I also saw substantially fewer attractive young women in sundresses and dapper young dudes; I saw substantially fewer people in general.

Waiting in a crawling line for a plastic cup filled with ice and bourbon late in the afternoon, I struck up a conversation with a middle-aged gentleman who said that he hadn’t been to Keeneland in twenty years.

“Back then, there weren’t nearly as many young people,” the man, who introduced himself as Hal, told me in a Kentucky drawl. “Now it’s changed. But back then, the young people didn’t have the money to come here and bet.”

Hal was on a roll.

“Back in the old days, black people weren’t even allowed in here,” he continued. There was an uncomfortably long pause. “Not that I agree with that. But that’s just how it was.”

As was true of almost every other patron’s outfit, Hal’s green sweater and blue blazer differed considerably from the fashion choices I’d seen at Aqueduct, or any number of the East Coast tracks that I frequented.

“This has always been more traditional than even Churchill Downs,” he said. “That’s why I’m dressed up. You don’t have any bums walking around here.”

Hal had a point. This could have been pre-game at the University of Kentucky versus Auburn football game, and I wasn’t an SEC fan. Where were the sweatpants and wheezing old men, the palpable stain that marks people who gamble too much? These staples of the East Coast racing circuit had yet to establish a beachhead at Keeneland. We shuffled forward, a little closer to the bourbon.


Up in the press box, I was relieved that the handicappers and working reporters, didn’t look nearly as spiffy. Tradition cuts both ways, and the typical frumpiness of my peers had played true to form, too.

The idea was both to watch the feature race from above the fray and to avoid the increasingly long lines at the betting windows. A computer terminal and an human were taking the press’s action. I placed my bet.

On the track, just in front of the packed apron, the starting gate opened up. Java’s War, the 4-1 second choice in the betting, showed little life, spotting the field several lengths from the start.

But the 1 1/8 miles of the race gave the three-year old the opportunity to rally, and after trailing for the first half mile, he moved up along the outside along the second turn, quickened as he moved into the stretch, and appeared to thrust his neck in front of Palace Malice at the finish line. I wasn’t the only one cheering in the press box. The old prohibition isn’t worth much in a sport with betting windows in the media sanctuary.

I held a few tickets featuring Java’s War, prompted both by a reading of the past performances as well as a brief encounter with his trainer, Kenny McPeak, in the paddock towards the start of the race day. Kenny’s earlier horse had landed me a winning ticket. “Kenny’s a very humble man,” a former assistant told me. “He never lost respect for none of his help.” Betting his horse seemed the least I could do.

So I was pleased that the humble man had a horse lined up for the Kentucky Derby, and even happier to be alive for the final leg of the Pick 3.


Making my choices 45 minutes earlier, I’d carefully handicapped the first two races, but had made some notably un-emprical decisions on the last one.  Wheeler, my guide from earlier in the day, was dating a trainer; his one horse on the day’s card was running.

But I decided to throw a second horse into the mix. A four-year old named Mezzano had been running well at Parx Racing outside of Philadelphia. It had been Philadelphia Park when I started at the races as a kid, it had lost its name – and perhaps a bit of its soul – after the grandstand was stuffed full of slot machines a few years back. The casino revenue did make for better purses, and thus better competition, but I didn’t visit much anymore.

And even with the enhanced purses, there remained a gulf in quality of racing – not as deep as the gulf in fan experience – between Keeneland and Parx. Still, I filled out the bet with sentiment rather than science and hoped for the best. A great many bets, perhaps including America’s Best Racing’s re-branding gambit, are made that way.

And sure enough, it worked out. Sometimes it does. Mezzano took the lead early, held the lead throughout, and cruised to victory. Back downstairs, in the late afternoon sun, I pumped my fist and clutched my ticket to make sure I’d gotten it right.

Everything I’d seen earlier in the day had served to highlight the aching gap between racing as I’d initially discovered it – an enfeebled, sinking game captive to grungy-ghostly venues, but one that still managed to captivate – and racing as it was practiced at Keeneland. For a brief moment, I felt the cord linking the two poles tighten. It’s nice to win, but it’s also nice to watch horses race in a beautiful setting, amongst a crowd of beautiful people. I was still smiling, ticket cashed and bills stuffed into my wallet, when I headed for the parking lot.

Images courtesy of America's Best Racing.

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