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William Nack
November 06, 2000
Riding with supreme skill and confidence since he quit drinking, Jerry Bailey is maintaining a steady pace as the finest jockey of his time
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November 06, 2000

Silky Smooth

Riding with supreme skill and confidence since he quit drinking, Jerry Bailey is maintaining a steady pace as the finest jockey of his time

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Down the backstretch and into the last turn, sailing along at almost 40 knots and with five tons of horses breathing fire around him, Jerry Bailey found himself in a familiar corner—all dressed up, in colored silks, with no place to go. It was Aug. 26, in the $200,000 Fourstardave Handicap on the turf at Saratoga Race Course, and the world's greatest jockey was clipping along the hedge on the 6-5 favorite, Hap, looking hopelessly trapped in seventh place as the field formed a wall around his mount, leaving him no room to run, no sunlight between all those flying shadows.

The poles flashed by, furlong by furlong. Bailey sat. Chalk players scrambled to the apron fence, shouting for Bailey to get free as the field thundered out of the turn. Bailey waited. Jockey Richard Migliore, trailing Hap on his mount, Altibr, had watched this scene unfold a hundred times. Over a 26-year career Bailey has always ridden patiently, Migliore says, sitting chilly when things got tight, but in the last two years he has seen in Bailey a coolness under fire that has raised his game to a new level. "A confidence," Migliore says, "that is unparalleled."

So there Bailey was, saving ground as he hugged the rail, with three horses fanned out in front of him on the lead, another beast directly behind them on the hedge, with Bailey tracking him, and two more just outside. Hap was raring to run. Migliore was wondering whether he should swing outside through traffic or sit tight behind Bailey, hoping that the rail would open. "Nine out of 10 times you can count on a hole opening, especially late in a race," says Bailey. "Horses get tired and they drift."

Migliore had no such confidence as the field raced for home. He was looking at Bailey and thinking, He's the favorite and I want to follow him, but there's no way he's going to get through!

So Migliore swung outside, and he had just started his charge when he glanced left in astonishment. The two horses directly in front of Hap had drifted off the hedge; quick as the pop of Bailey's whip, Hap dived for the hole before it could close, shooting the gap and grabbing the lead as he raced for the eighth pole. Migliore saw Bailey pulling away and screamed, "Oh, nooooo!" Having saved all that ground, Hap beat Altibr by three-quarters of a length. "A brilliant ride," recalls Hap's trainer, Bill Mott, for whom Bailey was the regular rider of the mighty Cigar. "He gets himself in the best position he can, then waits for things to develop."

At 43, on the eve of Saturday's Breeders' Cup at Churchill Downs, where he is expected to whisper to eight horses on the richest day of racing in the U.S., Jerry Dale Bailey has so excelled in the art of riding that for many longtime racing observers he has conjured up memories of the master himself, Eddie Arcaro, America's dominant jockey 50 years ago. " Bailey is the best rider we have had in this country since Arcaro," says Joe Hirsch, the dean of American turf writers, who has been at the Daily Racing Form since 1948. "He has the skill, the strength and the intelligence of Arcaro."

As Heady Eddie commanded the sport in the 1940s, so did Bailey rise to the summit through the '90s: smart and analytical, cool and professional. This was Bailey's decade-it all began, not coincidentally, just after he came to terms with his alcoholism and quit drinking—and, in the course of those 10 years, he won three Eclipse Awards as America's leading rider; four runnings of the $3 million Breeders' Cup Classic, America's richest race; four straight money-winning tides (1995 through '98), including a record $19.5 million in '96; two runnings of the world's richest race, the $4 million Dubai World Cup in the United Arab Emirates; all but the first of Cigar's 16 straight victories; and four Triple Crown races, including two Kentucky Derbys, on Sea Hero ('93) and Grindstone ('96). In the latter he fashioned one of the greatest rides in the 126-year history of the race, getting up in the final jump to win by a whisker.

"He had to make 10 or 15 decisions in that race, and he made every one of them right," recalls D. Wayne Lukas, Grindstone's trainer. "Angling, moving, sitting, waiting, going when the pockets opened. I don't think I ever saw anybody as determined to get there, absolutely on his belly the last eighth. There's no question—and I'll take this belief to my grave-that Grindstone was not going to win the Derby with anybody but Jerry Bailey on him that day."

Bailey grew up in El Paso, the son of a prosperous dentist, James Bailey, who owned a small stable of claimers that he raced at Sunland Park. Although Jerry started mucking stalls when he was 12, the thought of riding for a living never entered his mind until, limited by his size, he finally gave up hope of playing the games he really loved. "Football, I was too small," says Bailey, now 5'5" and 112 pounds. "I was the team manager. Basketball, I was too short; team manager again. Track, too slow."

Intensely competitive, he won a place on the high school wrestling team—he was a division champion at 112 pounds for Coronado High—and even considered riding in the rodeo. His good sense prevailed, however, and he turned to the one sport in which his size was as much an asset as his athleticism. He was off to the races, learning how to ride in the rough-and-tumble world of state fairs and small tracks. His mother, Betty, while dying of breast cancer, had asked him to attend college. Dutifully, he enrolled at Texas Western (now UTEP) to study accounting. "Numbers always fascinated me," he says, but he had grown used to the wind in his face, and he dropped out after a semester in the fall of 1975, a few months after his mother died.

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