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Authors: John Eisenberg

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With War Emblem’s victory at Churchill Downs in 2002, five straight winners and seven of the past eight were traceable to
the Dancer within four generations. To say the Grey Ghost was haunting America’s greatest race would be an understatement.
It was as if there was no end to the revenge to be exacted for his loss to Dark Star.

Remarkably, Vanderbilt wasn’t among the many owners and breeders who won major races with horses that traced to the Dancer.
Though he bred mares to the Dancer every year and certainly benefited in the 1950s and 1960s as the owner of such a sire,
Vanderbilt himself never bred another horse of the same caliber. After Kauai King was purchased out of a sales ring and won
the Kentucky Derby, Vanderbilt joked, “I guess I should be buying Native Dancers instead of trying to breed them.”

He tried to breed another with the same sire and dam in the 1950s; once the Dancer’s greatness was known, Geisha was never
bred to any stallion other than Polynesian. They had five full brothers and sisters, all bred by Vanderbilt, but none had
their famous brother’s class. Only three made it to the races, and just one, Geisha’s last foal, was able to win a race. “The
full brothers and sisters were nice horses with that good conformation and vigor, but they didn’t want to run like Native
Dancer,” Dan W. Scott told the
Thoroughbred Times
in 1998.

When Heidi Vanderbilt turned eleven in 1959, she received one of the full brothers as a present from her father. “His name
was Noble Savage,” Heidi recalled. “He had started on the track, but he was a terrible handful and not a good racehorse, and
that combination got him demoted. He was a dappled gray, about 16.1 or 16.2 [hands tall], not as pretty as the Dancer. I was
riding a lot and looking for a show horse, a hunting horse. It was not a great match. I was eleven and he was three. He was
too much horse for me at that age. When I was fourteen or so, we sold him. He was a very, very good jumping horse. I went
and saw him jump at Madison Square Garden. He went white-gray like his brother.”

Vanderbilt’s racing stable dwindled significantly after a phone call from Bill Winfrey, his trainer, in 1956, less than two
years after the Dancer’s retirement Vanderbilt, Winfrey, and jockey Eric Guerin had continued to race and win in 1955 with
a large stable including Social Outcast and Find, but then Winfrey, who had always eyed other professions somewhat enviously,
abruptly decided to retire.

“As my father told the story years later, he was literally leaving the house to go on a trip to Africa and the phone rang,”
Alfred Vanderbilt III said. “It was Winfrey saying, ‘I’ve raced the best for the best, I’ve had it, I’m through, I’m going
to retire.’ Dad said, ‘All right, I’m leaving, too. I’m going to retire, too. Sell the horses.’ It was a huge decision absolutely
made on the spur of the moment.”

Vanderbilt’s marriage to Jeanne had collapsed—their divorce was finalized in December 1956—and he was traveling extensively
as president of the World Veterans Fund, the money-raising arm of a federation of veterans’ groups in twenty-nine countries.
He had toured Asia through the first months of 1956 and was headed to Africa when Winfrey called. On May 21, 1956, a dispersal
of Vanderbilt’s racing stock was held at Belmont. Thirty-seven of his forty-two horses in training were sold, leaving only
old-timers Social Outcast, Find, Beachcomber, First Glance, and Crash Dive to race in cerise and white. Winfrey continued
to train the horses through 1957, fulfilling what he saw as his obligation to the stable before retiring. In the end, Find
earned more than $800,000, Social Outcast earned almost $670,000, and Vanderbilt’s foal crop of 1950 was regarded as one of
the greatest in history.

In 1958, Winfrey moved to San Clemente, California, with his wife Elaine, “certain as anything can be certain that I’d never
go back [East],” he told the
Blood-Horse
in 1985. Vanderbilt hired George Poole to train the stable—Poole had been John Gaver’s assistant at Greentree—but the stable
was no longer a powerhouse and Poole resigned in 1962. Vanderbilt continued to race a small stable through the years with
other trainers such as Mike Freeman, Bobby Lake, Rick Violette, and Mary Eppler handling the stock. Vanderbilt “never stopped
trying” to lure Winfrey back, according to Winfrey’s son Carey.

After moving to California, Bill Winfrey took real estate classes and pondered a career change but always came back to the
track. He spent most of the rest of his life in California, raising eight children. His family came first. “He felt that the
separations caused by the nomadic life of a trainer had ruined his first marriage,” Carey Winfrey said, “and by God, he wasn’t
going to let that ruin his second.”

Winfrey did come back East in 1962 when Ogden Phipps asked him to replace retiring legend Sunny Jim Fitzsimmons as the trainer
of the family’s Phipps and Wheatley stables. “It was my ego, I guess, that took me back,” Winfrey told the
Blood-Horse
. The job was the best in the country with Phipps-owned champion sire Bold Ruler filling the barn with talented homebreds,
and Winfrey won $1.35 million in purses in 1964 to break the record for a trainer held since 1947 by Calumet’s Jimmy Jones.
That year, Winfrey had the champion two-year-old colt, Bold Lad, and also the champion two-year-old filly, Queen Empress.
Bold Lad was a disappointment in the 1965 Kentucky Derby, finishing tenth as the 2-1 favorite, but another two-year-old star,
Buckpasser, came along that year and Winfrey again earned more than $1 million, finishing second in the country to Hirsch
Jacobs.

With many years of certain success ahead, Winfrey stunned the racing world by walking away from the Phipps job in December
1965. The Phippses were more hands-on than Vanderbilt, and while Winfrey told the
Blood-Horse
in 1985 that he was never second-guessed, he also said, “I just didn’t have a feeling of freedom there.” Carey Winfrey said,
“He walked away on principle from the best job in the country.” His replacement dominated the trainers’ earnings list for
the next three years, but Winfrey, ever the iconoclast, moved back to California and took his family to Europe for a year.
Elected to the National Museum of Racing’s Hall of Fame in 1971, he continued to train a few horses through the years. He
died in 1994 of complications from Alzheimer’s disease.

Unlike Winfrey, Eric Guerin had tasted victory in the Kentucky Derby, winning aboard Jet Pilot in 1947. He had three more
chances after losing on the Dancer, finishing third in 1955 on Summer Tan, sixth in 1956 on Career Boy, and thirteenth in
1971 on Impetuosity. Although his career peaked during his association with Vanderbilt, which ended in the late 1950s, he
continued to ride through the 1960s and early 1970s, finally retiring at age fifty-one. He was still active when elected to
the Hall of Fame in 1972.

After retiring, he worked as a mutuels clerk in New York for three years in the late 1970s, then underwent heart surgery and,
improbably, went back to the track and found work as an exercise rider, galloping horses for Hall of Fame trainers Allen Jerkens
and Woody Stephens. “He did it because he loved horses and wanted to be around horses,” said his nephew Frank Curry. “He was
in his sixties and still doing stuff teenagers do, just so he could be around horses.”

A costly divorce years earlier had lowered his lifestyle, but he remarried happily and spent more than thirty years with his
second wife. “He wound up later in life not having that much money, but the nice thing was, he had none of the surliness that
he might have had because he was winding up that way,” Jerkens said. “He was just as nice and easygoing as when he was riding
and winning. He was galloping horses for me, and he had the same wonderful patience with the horses that he’d had when he
was on top.”

After moving to Florida in 1989, Guerin worked as a mutuels clerk at Calder and Gulfstream, then became ill with a blood disorder
and died of heart complications in 1993. He was sixty-eight. His obituaries pointed out that he had won 2,712 races over thirty-five
years but would be remembered for losing the Derby in 1953: even in death, he couldn’t escape that defeat. “Eric Guerin was
a good man and a good rider, and he helped Native Dancer on numerous occasions,”
Daily Racing Form
columnist Joe Hirsch said. “ The worst thing that can be said about him is that maybe he didn’t help that one time.”

Guerin’s final rites, held in the winner’s circle at Gulfstream, were poignant. A musician played “The Lord’s Prayer” on a
harmonica, and Guerin’s son, Ronnie—the youngster of “Hi, Ronnie” fame, now almost fifty—spread his ashes in the flower beds.
Ronnie then turned to the small circle of mourners and said, “I would like to think that somewhere my father is riding Native
Dancer right now—and Dark Star, you don’t have a chance this time.”

Vanderbilt remarried in 1957 to twenty-year-old Jean Harvey of Chicago. They had three children and traveled extensively,
often with Broadway producer-director Harold Prince and Prince’s wife, Judy. “Alfred loved to travel, to probe, to learn,
and to have a good time,” Prince recalled. “We went to the Greek islands together, the four of us, and stayed on Mrs. [Joan
Whitney] Payson’s boat. Then we went to Russia. That was fun. We arrived at the airport in Moscow, and the minute they saw
his passport, they went nuts. It became clear that this was one of those names they had studied in their history books. But
what they had been damning to hell, the capitalist Vanderbilts, they also were duly impressed by. It was like the czar was
coming back. They saw Vanderbilt and decided I wasn’t Harold Prince, I was Prince Harold. We got on the coattails of that.
We stayed a block from Red Square. They gave Alfred and Jean the Lenin Suite.”

Ultimately, Vanderbilt’s third marriage also ended in divorce amid rumors that Vanderbilt, at sixty-two, was personally and
professionally fond of Robyn Smith, a twenty-nine-year-old female jockey. (Smith later married Vanderbilt’s friend Fred Astaire,
after Vanderbilt had introduced them.) Years later, Vanderbilt’s daughter, Victoria, said that when she had asked her father
about his life, he replied, “It’s pretty simple. I went to the races, got married, got divorced. Went to the races, got married,
got divorced. Went to the races, got married, got divorced. Went to the races.”

Although his racing stable never ranked among the national leaders after the 1956 dispersal, he remained prominent in the
industry. He made the cover of
Sports Illustrated
in 1963, the headline reading, “Alfred G. Vanderbilt Rebels Against Racing’s Establishment.” In the article, written by Alfred
Wright, Jimmy Kilroe, the director of racing at Santa Anita, said, “Looking at it from the standpoint of racing officials,
owners, breeders, trainers, jockeys and the racing press, I would have to say Vanderbilt is the most respected man in racing
today.”

Through the years, he remained involved in the industry as a Jockey Club member, president of the Thoroughbred Owners and
Breeders Association, and chairman of the New York Racing Association for four years in the early 1970s. He was honored with
the Eclipse Award of Merit, for lifetime contributions to the sport, in 1994. The New York Turf Writers voted him the Man
Who Has Done the Most for Racing four times.

“Racing was his heart and soul,” his daughter Victoria said at a memorial service after his death. “Sure, he loved pretty
girls and travel, his kids, his books and music, chicken hash at the ‘21’ Club and a good game of charades. But none of that
could compare to his passion for the sport of kings.”

It remained the constant in his life even as his travels around the world took him away for months at a time every year. He
always came back to the races and his beloved morning routine. “Even as he got older he continued to go to the track every
single morning,” Heidi Vanderbilt said. “He just loved the horses, the sport, the people. He loved watching the horses. He
loved the casual conversation that’s really what the track is all about. He would go and talk and watch. That was his breakfast.”

Gradually, the way of life he had been born into—the life he had always known—ceased to exist. Louis Cheri, his valet and
confidant, died. Sagamore Farm was sold to a developer in 1986. “He was a witness to huge changes in lifestyle,” Harold Prince
said. “Things that had been taken for granted started to just go away. But I never heard him call attention to it.”

Society changed profoundly around him, with generations of “new money” surpassing the old and its world of understated manners.
“He still had a lot of money, but he didn’t have billions, and he had devoted his life to a sport you don’t make money in,”
Alfred Vanderbilt III said. “I think his expectation was, ‘I’m still going to be Alfred Vanderbilt tomorrow,’ and that would
be a constant But it wasn’t. Things turned on their head in a lot of ways in the sixties. After the Beatles went on
Ed Sullivan
, what had been high [society] practically made you a pariah. All of our parents were baffled by what was happening and why,
and he was no different.”

But he still had his friends and family, his books and music, his dry wit and nonconformist’s outlook. “I interviewed him
late in life, and he didn’t look down on new things, like so many older people do,” Tim Capps said. “There was a traditional
part of him that wished racing could be like it was, when you drew 40,000 fans and everyone wore a coat and tie, but he knew
the world had changed. That told me, ‘Here’s a guy who has lived his life as a progressive, always a little ahead of other
people.’ ”

There was sorrow later in his life. His eldest son from his third marriage, Nicholas, was reported missing on a climbing expedition
in British Columbia, Canada, in 1984, and never found. Then, sadly, the onset of macular degeneration robbed him of much of
his sight “His life was filled with joy until the unfortunate latter days,” Clyde Roche said.

Though virtually blind, he still went to Belmont almost every morning, then returned in the afternoon for the races. “I would
talk to him every day by the rail,” Allen Jerkens said. “His chauffeur would bring him, and he would bring cookies for the
people he liked, people who rode the ponies and such. They’d come up to him and say, ‘Mr. V., where’s my cookie?’ A lady made
them for him. Sometimes he’d be a little tired and go home early. He couldn’t see well. He’d go by voices mostly. But he still
came.”

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