Native Dancer (11 page)

“As the situation developed, my father could scarcely believe it,” Carey Winfrey, Bill’s son, said years later. “His attitude
toward Native Dancer was one of enormous gratitude, that he had been given the gift of this fabulous horse when he was relatively
young in the game, at least compared to his father. He approached it with a sense almost of humility, that something so talented
could come into his hands, like a gift from the gods. He just felt so lucky.”

Born in 1916, Winfrey was originally named William Colin Dickard. His biological father, Claude Dickard, came from a prosperous
family that owned a cotton gin in Wills Point, Texas, a small town fifty miles east of Dallas. Claude married a Wills Point
woman named Mary Russell, went to college, and took a job with General Motors in Detroit, but he began drinking and the couple
divorced after having two children, Bill and an older sister, Janis. Mary took her children back to Wills Point. Claude committed
suicide, putting a rifle to his chest in a hotel room in Dallas and pulling the trigger. “He left a poignant note saying,
‘Take good care of my baby boy Bill,’ ” Carey Winfrey said.

Mary soon found another man in Wills Point. George Carey Winfrey was genial and dependable, and he adopted Mary’s children
and raised them as his own, doting on the boy, now named William Colin Winfrey. “My grandfather was just a lovely man, wonderful
to everyone, totally nonjudgmental, and funny,” Carey Winfrey said. “When he was in his prime, he would drive quite fast and
accelerate into turns; he was very robust and outgoing. He adopted my father, but he was more of a father than most people
are with their real sons. They had a very close relationship. Early on, they went places, just the two of them.”

In a 1985 interview with the
Blood-Horse
, Bill Winfrey said, “I had a thing about going out to the track with him in the morning. I didn’t want my father to go without
me. He’d be out there at the crack of dawn. He was a world champion hot coffee drinker. He’d have his finished, I’d be half
done, and he’d say, ‘Come on, Bill, let’s go.’ I loved it. It would be just Pop and me.”

George Carey Winfrey had become familiar with horses while working in a livery stable as a youngster in Wills Point before
the turn of the century. He dropped out of school to join the racing circuit and came to New York as a groom for Tokalon,
winner of the 1906 Brooklyn Handicap. He stayed in the East, worked for top trainers, and finally went out on his own. Thorough,
indefatigable, and more interested in horsemanship than self-promotion, he operated a small New York-based stable that featured
mostly claiming horses, lower end thoroughbreds available for sale whenever they race. Mary’s bracelets and rings were in
hock as often as they were on her hands, and there were times when George Carey’s gambling successes kept the family afloat
But he was an astute trainer and won his share of races. Known for jogging horses to keep them fit rather than putting them
through fast works, he was a favorite of knowing New York bettors. One spring, he won with ten of his first sixteen starters
at Jamaica.

“He’d stay in New York all winter, stabled at Jamaica, and you’d go up there in the spring and his horses would be big and
fat with long hair, and they didn’t look like they were fit, but they could outrun a spotted-ass ape,” recalled 1950s jockey
Charles Ray Leblanc, Guerin’s cousin. “[George Carey] Winfrey was a hell of a trainer. He and Hirsch Jacobs were probably
two of the greatest there ever was.”

Bill and his sister were inured to the nomadic racing life as Depression-era youngsters, spending winters in New Orleans and
summers in New York, Maryland, or wherever their father raced. When Bill was six, he rode a circus pony named Sparkle to a
victory in a staged-for-grins race at Hialeah. At ten, he was handing out betting numbers on the backsides of tracks. At fifteen,
he dropped out of school while on a winter sojourn to Miami with the stable and became his father’s fulltime assistant. He
had started at John Adams High School near Aqueduct in New York, but his parents hadn’t come south with the proper papers
to enroll him in school in Florida, and he convinced them he preferred the racetrack to higher education anyway. Although
he was thrilled that his goal of becoming a jockey was near, he later regretted that he had ended his academic career prematurely.

He took out a jockey’s license at age sixteen, intent on proving his mettle despite his youth. But he weighed ninety-one pounds
when he took out the license in January in Florida, and he was up to one hundred ten pounds by the Saratoga meeting in August.
He won just four races in nine months before giving up on the project. “I was long on weight and short on talent; just plain
no good as a jockey,” he told John McNulty in their
New Yorker
interview in 1953. He became an exercise rider and a groom, and that fall his father gave him a small string of horses to
take to Laurel, a track in Maryland. He handled the assignment deftly, and his future as a trainer began taking shape.

Before that happened, though, he left the track for two years in the mid-1930s to work for Eddie Burke, an indomitable bookmaker
who had played on pro basketball’s original Boston Celtics and mar-

ried Winfrey’s sister, Jan. Bookmaking was still legal in New York—pari-mutuel wagering didn’t arrive until 1940—and Winfrey
wrote prices and ran information in Burke’s betting rings. He was good with numbers, but he had to return to the barn when
his father suffered a heart attack in 1937. He ran the stable until his father returned the next year, then started his own
public stable in New York.

The young Winfrey lived on the edgy flow of the claiming game, buying cheaper horses right off the track and then—hopefully—raising
their value and selling them for a profit after a few wins. Winfrey was twenty-two years old, competing against keen veterans
such as Calumet’s Plain Ben Jones, but he held his own. It was said you could count on one hand the trainers who had claimed
useful horses off Jones over the years, but Winfrey pulled it off when he claimed a filly named One Jest, earning a smiling
rebuke from Jones; the Calumet trainer and Winfrey’s father were old friends.

He won his first stakes race in 1938 with Postage Due, a horse he had claimed off Vanderbilt, then turned a filly named Dini
he had claimed for $2,000 into a top sprinter, winner of twenty-seven races. Raised among old school racetrackers, he was
as businesslike and taciturn as he was insightful, preferring to let his horses do his talking. In 1940, he took on several
wealthier clients, married a pretty brunette, and soon fathered a son. “He was developing a reputation as a good horseman
and a square shooter,” Carey Winfrey said.

When World War II broke out, he first tried to join other horsemen in the Beach Patrol, a Coast Guard unit patrolling Florida’s
beaches on horseback, looking for German submarines. He wound up enlisting in the Marines and becoming a rifle coach.

“Before he went into the service, they were having a party,” Carey Winfrey said. “He asked his sister to take a walk around
the block. She didn’t know if he was going to impart some wisdom or ask her to take care of me or my mother or whatever, but
they walked all the way around the block and he didn’t say a word. Then, when they got to the end, he said, Want to go around
again?’ She said sure. They went around again and he still didn’t say anything. And then he left the next day. To her dying
day, she wondered what it was he was trying to say that day.”

After serving in the South Pacific on Guam and Truk, he was discharged in 1946, came home, and began rebuilding his public
stable. He soon had fifteen horses, including several stakes winners. Then Vanderbilt hired him. “Alfred used to come by when
I was running Dini; he’d be there in the paddock, and we’d chat, but I didn’t think anything of it,” Winfrey told the
Blood-Horse
in 1985.

The wealthy young sportsman and his new trainer had a lot in common. Both had halted their education prematurely to pursue
racing. Both were on their second marriage; Winfrey’s first had collapsed, the long separations caused by war and racing taking
a toll. Both were reserved in public and indifferent about spending their afternoons with society swells in trackside boxes,
preferring mornings at the barn. Though raised in different circumstances, “they were kindred spirits,” Carey Winfrey said.
And as much as both loved racing, they had facile minds and broad interests beyond the game.

“My father felt the greatest mistake his parents made was letting him quit school to become a jockey,” Carey Winfrey said.
“He felt it totally circumscribed his life and eliminated options. I don’t think he went through a day when he didn’t contemplate
another career. Not that he didn’t love what he was doing. He just felt there were so many other things he might have done
that he didn’t get to do. He went water-skiing one day, then never again. He just wanted to experience things. He talked about
being a lineman on a telephone line. He was always fantasizing about other professions.”

Elaine Winfrey, to whom Bill was married for forty-two years, until his death in 1994, said, “It was strange, a man so accomplished
in one field wanting to do other things. But he was quite intelligent for a man that didn’t have a formal education. He took
night classes and thought about getting into real estate. He felt it was somehow beneath a man to spend his life training
horses.”

It wasn’t beneath him in the early 1950s. Short, trim, and well dressed, he took Vanderbilt on smiling strolls to winner’s
circles across the country. “They had a great relationship, the best,” Elaine Winfrey said. “Bill respected Alfred, and Alfred
respected Bill. Alfred never interfered with what Bill wanted to do. There was no one better to train for. Bill knew it.”

Vanderbilt, in turn, introduced Winfrey to Fred Astaire, Gregory Peck, and a high life he had never imagined as a boy. “Bill
and Fred Astaire became good friends,” Elaine Winfrey said. “We’d go over to his house, and Bill and Fred would play pool
and I’d watch a movie in the screening room.”

But success never swelled his head. Winfrey was loath to accept applause for his training, preferring to credit his father,
his horses, and racing luck. “He never took credit for anything,” Carey Winfrey said. “He thought bragging, being boastful,
was sinful. He would say, ‘Well, you know, it’s the luck of the draw’ or ‘Good horses make a trainer look good.’ Who knows
how much of it was true? He knew what he was doing. He’d learned a lot from my grandfather and he put it to use. On the other
hand, once he was with Alfred, he certainly had the kinds of horses he’d never had before. But regardless, he was modest,
always modest. Once we went into a store and the guy behind the counter was going on about what a great trainer Winfrey was
and how great Native Dancer was, and my father said, ‘Yeah, yeah,’ and never identified himself. At some fundamental level,
he was insecure or shy or something, because he was always self-deprecating. Just a modest man. He almost made a fetish of
being modest.”

That was never more evident than when he was interviewed by McNulty for
The New Yorker
. “Tell the truth, a man my age doesn’t deserve a horse like this,” Winfrey said. “My father is sixty-eight, training horses
all his life, and he’s never had the luck to handle a horse like this grey. I know many trainers who are seventy, seventy-five,
training horses for fifty years or more, working hard, knowing the business much more than I know it, and they never had the
luck to get a horse like this grey. Tell the truth, a man of thirty-six doesn’t deserve it, that’s all.”

His respect for the older man who had shown him how to train a horse was enduring. Whenever strangers introduced themselves
at Barn 20 and asked for “Mr. Winfrey,” Winfrey waved in the direction of George Carey’s barn across the backside and said,
“I’m Bill Winfrey; my father, over there, he’s Mr. Winfrey.”

“My father, to his dying day, claimed my grandfather was much the superior horseman, and that was probably the case,” Carey
Winfrey said. “My grandfather could make bad horses run faster than just about anyone. My father was probably a better manager
of the stable and better at the politics and stuff, but as far as a horseman, he always felt my grandfather was the real horseman.”

But it was Bill Winfrey, not George Carey, into whose hands Native Dancer had dropped, and now, with an undefeated juvenile
season behind them and the Kentucky Derby looming, it was up to the son, not the father, to make sure the horse realized his
full potential in front of a nation of racing fans.

“There was a great deal of interest in the horse,” Dan W. Scott recalled. “I spent a lot of time with Bill, went to some races
with him. He had a great time. He would paint Native Dancer’s ankles with iodine just to make people think he was worried
about them, when he wasn’t. He was having fun. And he did a wonderful job. Native Dancer had all those muscles, and Bill took
care of them and made sure they kept growing. The horse was lucky to have such a trainer. But Bill wasn’t sleeping well. He
was constantly worried about doing the right thing. He’d say to me, ‘This horse can train himself, he’s that good.’ A horse
like that is a gift. I knew it. Alfred knew it. Ralph Kercheval knew it. Bill certainly knew it. And Bill didn’t want to be
the one to mess it up.”