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"Put him back on the horse," Bray said. "I want to see if he can ride him that bad again."
Stephens did win one more race, and he and one of the rival jocks, Joe Bollero, still laugh about it 53 years later. Bollero was fighting weight at the time, and money was getting tight in the Depression. It was a rough-and-tumble business on the racetrack. Joe had bet his entire fortune, all of $300, on his mount in the sixth at Hialeah on Jan. 28, 1931, a filly named Watch Girl who was better than she looked. She was almost 10-1; Stephens, on Directly again, was 8-5. Figuring that Directly was the one horse he had to beat, Bollero approached Stephens in the jocks' room, showed him three $100 win tickets on Watch Girl and said, "Why don't you take a ticket and make a little money?"
Stephens recoiled. He was a young man fresh off the farm and riding a horse for his boss. He said no thank you. Instead, he rolled to the lead, heard friends yelling to him from the backstretch fence—"Go on with her, Woody!"—looked back as Joe tried vainly to catch him on the turn and then yelled, "How much you want to give me now, Joe?"
And Stephens went on with her. Directly won by a head from Madelon, and Watch Girl faded to third. As they pulled their horses up, Joe looked over at Woody and yelled, "I reduced for a week to ride this sonuvabitch. I don't have to worry about that now. I don't have anything to eat with!"
It was the last race Stephens ever won. He struggled for a couple of years, but to no avail. Ward finally broke the news. "If you have a future in racing," he said, "it's in training, not riding." Says Stephens, "When he saw I wasn't going to make it as a rider, he didn't give up on me. He always liked me. He wanted me to make it. He could have let me go. I don't know what would've happened to me if he had." Anyway, Ward didn't, and five years after Woody had ridden his last winner, racing had itself W.C. Stephens, trainer.
That was in the spring of 1936, when Stephens was galloping a fast horse of Ward's named Deliberator and took him to the old Latonia racetrack in Covington, Ky., to campaign. "Put your name [as trainer] on the program," Ward told Stephens. "It could do you some good." So it was that he saddled his first winner on June 18, 1936, in the sixth race at Latonia; Deliberator beat Crowning Glory by a neck. "Trainer: W. Stephens."
He was officially a horseman. But it wasn't until eight years later, in the summer of 1944, that Stephens really earned the title. After leaving Ward in 1937, the year he married Lucille, Stephens went on his own for a spell, then hooked up in 1940 with a crusty old trainer named Steve Judge, who asked him to take his promising 3-year-old, Our Boots, to Hot Springs, Ark. to train for the 1941 Kentucky Derby. Woody jumped at the chance, and three months later brought Our Boots to Kentucky to defeat Whirlaway in the Blue Grass Stakes.
Judge was a character. "He was a street player out of Oakland, California," Stephens says. "Slept at the barn a lot. He never believed in a necktie. At night he cooked a pot of beans. If he won a race, he'd throw out the beans and put on a chicken. He could train horses to go long and short. Tough and mean on a horse, but no one ever said he wasn't a good horseman. Mr. Judge was a tough, tired old horseplayer. But he had a way. When he put in a good word for you, people listened."
In 1942, when Judge heard there was an opening for an assistant to trainer Ross Higdon at the Woolford Farm, he had Woody dress up in a coat and tie and took him over to the box of Woolford Farm's owner, Herbert J. Woolf. Woolf was at the track with Ginger Rogers that afternoon. Judge recommended Stephens for the job, and he was hired. "Woolf was a big clothing man out of Kansas City," Stephens says. "Knew the big Hollywood types. He had something to do with Jean Harlow coming to Hollywood. For as long as I knew him, until he died [in 1964], he always sent me for Christmas six ties, six shirts and a light raincoat."
Stephens worked for Woolf and Higdon for only two years. Higdon wasn't much. "He had a big stable, but all his horses were sprinters," Woody says. "They couldn't get a route. He was a big feeder. His horses all carried a lot of weight. He chewed tobacco and had ulcers. He was a Sunday trainer—you know, easy on his horses. His horses were soft."