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By the time Woody Stephens won the 100th Kentucky Derby with Cannonade in 1974, and the 1984 Derby with Swale, he was already famous — a fellow who began with nothing, but made himself something, fitting right in on the track, and with the captains of industry and socialites of Park Avenue, for whom he trained blue-blooded racehorses. Stephens possessed an innate sense of how to be himself in any company, and his horses could win any race.
Stephens started out life dirt poor, the son of a farmer in a little town not far from Lexington, Ky. — but far enough that the rich earth of the Bluegrass did not carry to his father’s tobacco farm. Because he was always a little smaller than other boys his age, he gained a special affinity for horses, beginning on his family’s farm.
“One of the reasons I developed a liking for horses early on might have been the fact that when my dad hoisted me up on one of them, or on the back of one of his mules, I was five or six feet higher off the ground, looking down at people instead of up.” Stephens recalled in his autobiography, “Guess I’m Lucky,” written with writer James Brough. “I got that boost up in the world, starting when I was three or four years old. He let me ride them as they pulled the hitch that did the plowing. It provided more pleasure, I found out later, than hoeing tobacco for fifty cents a day. Dad used to say, ‘Woody’s a born horseman,” and I was happy to hear it, because I didn’t want to be considered a born field hand.
“When I started in school,” Stephens continues, “I got my own pony given to me by my grandfather. I was six years old. I rode “Bill” the three miles there in the morning, taking feed for him and lunch for me. I’d keep him in a little livery stable, an open shed, while I was at my lessons. Then at lunchtime I’d ride him a half mile down the road to a creek to give him a drink of water before I brought him back.”
Stephens’ dad and mom moved the family to Lexington later and young Woody fell in love with the races. He started out on the turf as a jockey – well, actually trainer Sherrill Ward started him off as stable apprentice, grooming horses and exercising them. The racing life took Stephens all over. As an occasional jockey he had a hard time keeping his weight down – and his victory total above zero. Eventually, he turned to training, with the help of several prominent horsemen, finally hitting it big when he moved to New York and teamed up with a professional horseplayer named Jule Fink. Fink supplied Stephens with cheap horses that the young trainer was able to improve. Woody would get them ready, Fink would bet, and the horses – more times that not – would go to the front, and not look back.
Over time, Stephens stepped along in company until he was handling the blue-ribbon steeds of blue-blooded Park Avenue owners. Those horses won, too. Capt Harry S. Guggenheim, of the famous Guggenheim art family was one, and there were others. Stephens and his wife Lucille loved the life and fared well in it. Woody, as everyone called him, was a favorite of bettors, and a hero to fans, and more than fabulous telling stories and offering sage opinions on racing. There was nothing like catching Woody holding court at the classy upstairs bar at Hialeah Park, with his customary scotch. Woody could talk as well as he could train.
Even though he’d already won the Kentucky Derby and many other important races, a zenith of Woody’s training career came along in 1982, when Stephens turned up with the best 2-year-old in the country, Devil’s Bag.
“A good two-year-old is about as dependable a horse as you can wish for, bursting with energy, eager to do his best, not trying to save his legs like an older horse,” said Woody. “If he’s trained right, he shouldn’t be balky or spoiled.”
Devil’s Bag sparkled at two, and was favored for the 1983 Kentucky Derby. But when the Derby prep season commenced in Florida, Stephens felt something wasn’t just right with the Devil. Or with himself. In Lexington, Stephens’ cousin, Dr. David Richardson, took one look at Stephens and slapped him in a hospital to be treated for pneumonia, complicated by chronic emphysema. With his wife Lucille at his side, Stephens made progress, and Richardson finally sprang him for the Kentucky Derby.
But it was without Devil His Due. The horse was going lame in a front foot, but nobody could figure out why. Veterinarian Gary Lavin found a tiny fracture in his opposite foot, which Stephens surmised was causing the horse to put abnormal weight on the other foot – and Devil His Due was out of the Derby. The trainer had Derby Fever, and a fever of his own.
But things happen in horse racing. Sometimes good. A second Stephens colt named Swale, owned by Claiborne Farm, was suddenly blooming. Getting better by the day, even if the trainer wasn’t. Stephens reached out to the West Coast for jockey Laffit Pincay. Pincay rode boldly, and Swale won the Kentucky Derby. Woody went home to bed, pleased.
The trainer was his regular chipper self, though, for the 100th Derby in 1974, when jockey Angel Cordero steered Cannonade to victory in a Derby-record field of 24 horses, before a record crowd of 163,628 sun-drenched fans. With Cannonade’s owner John Olin unable to attend because of his health, Stephens accepted the gold Kentucky Derby trophy from Britain’s Princess Margaret. The day after the Derby, Woody admitted he was a little awed, when it all sunk in. Chatting with reporters on the back fence, he waved across the way to the ancient Twin Spires. “Imagine,” he said, “a poor boy from Stanton, Ky., up there on that stand with the Princess of England.”