Cigar Aficionado

Blustery, fall winds blow across Belmont Park as 54,000 thoroughbred fanatics crowd the stands. Horses are scrutinized, racing forms are perused, and an edge of big-time intensity permeates the air. Up in the glass-fronted owners' box, the atmosphere is elegant and moneyed. One man parades around in a baseball cap adorned with the Hermes logo and holds a flute of Champagne in each hand. Several women are turned out in ballooning skirts. Men sport tweed jackets, neckties and expressions of deep concentration. New York Racing Association chairman Barry Schwartz strolls down to the Belmont paddock, ing serious bettors who mentally crunch nuggets of horse-related data. Betting on thoroughbreds, after all, is not a spin-of-the-wheel no brainer.

Fanciers of this particular wager insist that it's an intellectual pursuit, fueled by information and comparative analysis, pitting bettor against bettor—rather than against the track, which earns its money via commissions and adjusts odds accordingly. Indeed, horse racing ranks as the one sport bet that directly challenges gamblers to out-pick their neighboring know-it-alls.

ittedly, today does not represent just any day at the races. It's the afternoon of the 2001 Breeders' Cup, one of racing's premier events with a purse that exceeds $14 million. Bud-slugging guys, wearing Windbreakers and placing $2 bets, are clearly in the minority (or at least laying low), and Belmont vibrates with a kind of highbrow, big-budget elegance that suits the sport of kings.

Cast from "The Sopranos" are in attendance. So are Kiwi supermodel Kylie Bax and former New England Patriots coach Bill Parcells. The final race proves so compelling, with a 7-to-1 long shot called Tiznow unexpectedly coming from behind to win its second Breeders' Cup Classic in a row, that Parcells' replacement, Bill Belichick, will show a video of the race six weeks later to the Patriots as a motivating tool. Beyond emphasizing the resurging pervasiveness of racing, the ploy actually works: New England doesn't lose another game all season and goes on to snag the National Football League championship by upsetting the St. Louis Rams, 20-17.

But it's not just strategizing coaches who glean inspiration from fast-running horses. Shepherding in a new, young crowd to enjoy the glories of racing is 24-year-old Ogden Phipps. On Breeders' Cup day, Phipps is with friends and family in the Trustees' Room—an unpretentious enclave that features an elaborate buffet and wall-bracketed TVs on which races are closely monitored by horse owners and VIPs. Unsatisfied with a small-screen view, however, Phipps continually darts from the Trustees' Room to the stands to catch each race up close and in person.

"Racing is in my blood," says Phipps, not exaggerating at all when you consider that his family's involvement in breeding and owning horses stretches back four generations. "Gambling is fun, but to enjoy racing you really have to look at these horses as incredibly graceful athletes. They weigh 1,100 pounds and run 35 miles per hour. It's a lot of speed for something that big."

Phipps, an investment banker with Goldman Sachs, is sufficiently enamored with the sport that he builds his summers around race weekends in Saratoga and invites a dozen or so friends to hang out in his big family house up there. Visitors, going to the track for the first time, are invariably impressed by the way racing offers a kind of civilized accessibility to the athletes—equine and human.

"You go down to the paddock, have interaction with the participants, spend a pleasant afternoon at a beautiful racetrack that's probably situated in one of the nicest parts of the country," enthuses Phipps, noting that his family raced Personal Ensign (the only horse to retire undefeated in 80 years) and has six Breeders' Cup wins to its credit among the various horses it has entered over the years. "Racing is becoming a cool thing. The last Kentucky Derby was packed with young people. You had the Backstreet Boys there; Reggie Miller was there. Racing people like to have fun: we dress up, go to great parties. Sometimes it feels like a throwback to a more elegant era." Fronting the campaign to keep racing on an upswing of growth, which merges state-of-the-art computer terminals with the old- fashioned adrenaline-infused kick that once defined this sport, is Barry Schwartz, who was named chairman of the New York Racing Association in 2000. Schwartz, a lifelong fan and longtime owner of thoroughbreds, has the sensibility and business smarts to take racing where it needs to go. "My challenge is to make New York racing as good as it can possibly be," Schwartz says, sitting in his Belmont office on the afternoon before the Breeders' Cup. "We already have the best horses and the best jockeys, which add up to equal the best racing. My job is to continue that trend and make it better. For most of the year, we have one of the strongest rider colonies in America—and, not coincidentally, the largest handle in the country. People follow money. Horses follow money. And as long as our purses stay big, we will get the best people and horses to race here."

Schwartz is a slender, stylish man who looks great in his Calvin Klein suit—which comes as no surprise when you realize that he's not only chairman of the clothier but also helped boyhood friend Klein launch the company in 1968 with an initial investment of $10,000. Like Klein, Schwartz grew up in the Bronx, where gambling was a common pastime. "Everybody was in action," Schwartz re. "We bet ball games, went to races, shot pool. It was part of my background." So much so that when Schwartz considers the four months (yes, months) he spent at New York University, he half-brags, "I majored in billiards at the Loeb Student Center—the place where you could play three-cushion."

Well aware that all gamblers are lured by good returns on their wagers, one of the most significant things Commissioner Schwartz did was reduce the takeout—the amount of money retained on all wagers—at New York State tracks. It's currently at 14 percent for win, place and show betting (down from 15 percent), which ranks among the lowest in the country, and he hints that it might drop further. "The decrease in takeout is offset by a seven percent increase in betting," says Schwartz. "My goal is for this to be so successful that I can go back and keep lowering it. With a 10 percent takeout, the size of our handle will become enormous." Schwartz considers this, then proudly adds that his decision was totally contrarian to industry wisdom: "Business got tough, so racetrack operators all over the country raised their takeouts. You don't do that. Where I come from, you lower your price when business is bad."

Other buzz builders will include video lottery machines at a handful of New York tracks (they might not bring upscale gamblers, but they will contribute to richer purses, which will make for better racing) and enhanced advertising (a former Calvin Klein creative director is now handling the NYRA; one ad features a decked-out model in the stands and it asks, "Looking for a great filly?"). Currently, Schwartz is embroiled in a battle to take control of the local Off Track Betting, which is operated by New York City. "The OTBs in New York are horrible," Schwartz groans. "Our plans for OTB would involve closing a number of them and building some new ones on a much higher level."

Schwartz's personal and financial interest in racing increased in the late 1970s, when a Calvin Klein licensee let slip that he owned a lot of horses—including a champion filly named Chris Evert. Schwartz heard this and responded, "I'd love to own a horse." He was quickly hooked up with a good trainer and soon became the proud proprietor of a thoroughbred. "Buying one horse didn't seem like a big deal at the time, but it's come a long way," says Schwartz, who now has more than 100 in his stable. "Words can't describe what it's like to have a hot, winning horse. The highs are incredibly high and the lows are incredibly low. You go through bad periods. But if you come up with one good horse, and he wins one big race, well, it wipes out all the aggravation."

When Schwartz considers a horse that took him through a gamut of deep emotions, he immediately thinks of Three Ring, a filly of his that finished second in her first start, won a couple of major stakes races, and showed in the Breeders' Cup. "Her wins were so impressive that we ran her in the Kentucky Derby," recalls Schwartz, emphasizing that having a horse in that race is the brass ring for any thoroughbred owner. "She got knocked sideways coming out of the gate, the saddle slipped, and the jockey couldn't control her. She finished last, but came back to win the Acorn Stakes at Belmont. All of her wins were unbelievable highs." He hesitates for a reverential beat, then adds, "Prior to her next race, the Mother Goose, also at Belmont, she reared up, fell back, split her skull open, and died in front of us in the paddock. In 10 starts she won more than $750,000. Then one day she got killed, just like that. It was the worst experience I ever had in racing."

Despite the heartache, Schwartz never came close to selling his racehorses. Beyond the pageantry and attention and thrills—not to mention the elite company of fellow owners like Houston Texans founder Bob McNair, the late Gene Klein (he sold the Chargers and vowed to spend the proceeds on horses), and Executive Jet Chairman and Chief Executive Officer Richard Santulli—Schwartz loves the genealogy and science that goes into breeding. He loves that somebody once offered to buy an early winner of his for $900,000—"I thought that horse was heading for the Kentucky Derby, and didn't sell; in retrospect I should have." In owning and breeding horses, Schwartz finds the kind of rush that eclipses even the headiest bets he might have made back when he was a serious handicapper who picked horses the way he currently picks wines: searching out good values and undiscovered gems. "These days," he says, "the bet is in buying the horse. When I breed to a horse with a stud fee of $400,000, isn't that a big enough bet? I'm betting that the mare will produce a horse that generates over $400,000 in winnings." He shrugs and adds, "But, hey, I'm an action guy."

A sure bet, where Schwartz is concerned, seems to be the growth of racing under his stewardship. Four months after the Breeders' Cup, sitting on a sofa in his gargantuan office at Calvin Klein's midtown Manhattan headquarters, Schwartz marvels over numbers that are much bigger than any single wager or horse. He talks about how the 2001 Breeders' Cup generated $100 million in bets from across the country. And he proudly points out that New York track attendance is up: it rose 14 percent in December 2000 as compared to the same month in the previous year, and did nearly the same thing in January 2001. Then he acknowledges that part of the reason for the climb stems from his decision to offer free track issions in the winter (normally it's only $2—and the saved money surely gets spent at concession stands or betting windows). "You've got to have people in the seats," he says, adding that he's encouraging fans to make a picnic of it when they come to the track. "Racing is an exciting sport and it's sad to see empty stands. I in the late 1950s and early '60s when there would be big crowds every weekend."

Then he glances at a TV monitor built into the wood-ed wall alongside his desk. On-screen a race is about to start. Schwartz focuses on Navajo Code, one of his thoroughbreds. "That horse has been a real disappointment," Schwartz its. "Navajo Code has got a lot of speed, but not a lot of heart." Nevertheless, the horse thunders out of the gate and looks damn good through the first turn. "The start of a race is no problem," deadpans Schwartz, not sounding confident about his horse's prospects. "Finishing the race is Navajo Code's problem."

Defying expectations, Navajo Code holds a money position into the home stretch. Ultimately, the horse finishes third. Schwartz looks perfectly pleased as he states, "That's the best race this horse has had." A few minutes later he gets a call from the horse's trainer. They have an all-good-news chat. He hangs up and our conversation turns to the topic of elite races and their importance. This is when Barry Schwartz allows that a few of his horses, besides ill-fated Three Ring, have run in the Kentucky Derby. That, he says, is the best. "Nothing is as exciting. And one day I plan on winning." He smiles at the obvious folly of crystal-balling a far-off sporting event, then adds, "Just like everybody plans on winning it."

Sure, it's a dream. But, as Schwartz says, "Dreams are what keep this sport going."

Michael Kaplan writes frequently about gambling for Cigar Aficionado.