Jim Conway, a leading trainer for several large stables over the last twenty years, was training the Darby Dan horses. Olin Gentry, a veteran Kentucky horseman, managed the farm. Both men were widely respected in the business, though neither happened to have too much respect for the other. "Farm managers," Conway has said, "love to criticize the men on the racetrack. But if they were really so good, wouldn't they be here where the big money is?"
Olin Gentry had done well enough on the farm. For 24 years he had managed Idle Hour for Colonel E. R. Bradley. He joined Galbreath in 1946, left him in 1949 to manage Mrs. Ada L. Rice's farm and returned to Galbreath in 1956. He had shown a good eye for a horse and ample ability to run a successful farm operation. He also held the traditional farm manager's disdain for trainers.
Even so, in the midst of plenty, Gentry and Conway managed a peaceful and very profitable coexistence. But when Darby Dan fortunes tailed off during the next two years, relations were strained. Graustark, who might have initiated a whole new era of success, was placed squarely in the center of a touchy situation.
The chestnut quickly established himself as the most precocious of the new two-year-olds at the St. Lucie training center in early 1965. Under the care of Boo Gentry, Olin's 41-year-old nephew, he breezed a quarter mile in 23 seconds in early February. "But when I went down there to inspect the new two-year-olds," Conway said, "they never showed me Graustark."
Boo Gentry was sent to Chicago with a smaller string of horses—including Graustark. In July Conway began reading about the colt's remarkably fast workouts. A month later Graustark had won two races, and he was being hailed the most exciting colt to arrive in years. Conway listened to the talk and said nothing. Then on August 18 he resigned.
"There were no secrets kept from Jim that I know of," says John Galbreath. "We told him at the beginning of the year that we had too many young horses to race in one place. So we sent Boo to Chicago with some of them. We didn't know anything special about Graustark. At least I didn't."
Because of his breeding and early speed, Conway felt that the Gentrys had known something special about Graustark. When Galbreath himself tried to correct the situation, Conway remained firm. "Mr. Galbreath was very good about it," said Conway. "He even talked about sending Graustark to me. But I don't want to force a man to do something for me. We've had a pleasant association, but now I think it's best to end it."
Galbreath and Conway parted on good terms, and each man retains respect and liking for the other. But the end of Conway's six-year tenure at Darby Dan marked the beginning of the most trying year of Boo Gentry's life.
Gentry is a big, boyish-looking man who was nicknamed "Boo" by a groom many years ago. He is a capable horseman, but he is shy and extremely nervous. He talks rapidly in short sentences, frequently asking, "You understand, don't you?" Around the barn, he paces constantly, chewing gum and jabbing sticks of straw in and out of his mouth. He grew up near horses and learned from his uncle, Olin, and his late father, who also was a trainer. He proved his own ability in the last two years when he developed such good colts as Umbrella Fella and Royal Gunner for Owner Michael Ford. But Boo Gentry has always been at his best with smaller stables. He left a job with Capt. Harry Guggenheim's large Cain Hoy Stable after two years, saying, "I prefer a smaller outfit where there is less pressure."
And last fall, Boo suddenly found himself under the most intense pressure that racing can produce. He was left with a powerful array of Darby Dan horses—including one of the early favorites for the Kentucky Derby.