"I rode into that winner's circle," he said.
Directly paid $37.70, making Stephens $357 on his bet, and back at the barn he was full of himself. He led the filly around the walking ring to cool her out and then gave her to the groom. Booty Taylor, the stable foreman, said to Stephens, "Now get out there and rake that walking ring!"
"But I'm a jockey now," he protested.
Booty snorted. "You may be a jock in Mr. Ward's book, but you're still a punk in mine."
Stephens was born in Stanton, a little town in the Kentucky hills, on Sept. 1, 1913, when the nearby Bluegrass country was developing into the thoroughbred breeding capital of America.
Stephens lived in Stanton for 10 years, until his father, Lewis, and his mother, Helen, moved the family—Woody has three younger sisters, Jane, Anne and Mary, and a younger brother, Bill, himself a trainer—to a farm just outside of Midway, a hamlet where mules pulled wagons over rutted dirt roads and a railroad passed through. His father was a tenant farmer, sharecropping the land, growing tobacco, raising a few pigs and cows. The boy grew up on the backs of the mules that pulled the hitch that plowed the fields.
"It was hard work on that farm," Stephens remembers. "I can still see that milk bucket bouncing off my father's leg at five in the morning on his way to the barn to milk those cows. Then going to those fields to work. My mother would be up at 4:30, fixing breakfast. He'd be in the fields at six, driving those mule teams. I hoed tobacco for 50 cents a day. I worked all day, from when you can't see till when you can't see."
Woody rode three miles to school on his pony, Bill. One morning he came to a fork in the road and a black man was hanging by a wire from a tree. They said he had broken into a warehouse holding barrels of whiskey and killed the night watchman. The Klan took him out of jail and lynched him. "We were walking right under him going to school," Stephens says.
Stephens went to school until February 1929, halfway through his freshman year of high school, when he skipped to join the racetrack, under John Ward. There he befriended John's son, Sherill, who many years later would train Summer Tan, conqueror of Nashua, and the great Forego. "I came to the racetrack to be a rider," Stephens says. "I never dreamed of being a trainer."
Stephens was never, as he complained to Booty Taylor, a jockey now. Oh, he did win on Directly that first time out at Hialeah, but he was awfully light at 85 pounds and, always small and delicate as a child, not strong. In fact, a week after Directly broke his maiden for him, Stephens rode her again, lost the lead inside the eighth pole, finished second and got censured by the official chart caller, who wrote: "Directly...was under restraint to the stretch, but her rider was of little help to her at the finish." One day Stephens finished second on a horse called Brandon Dare. Afterward, the horse's trainer, Frank Bray, was asked if he wanted to switch riders next time.