Silky Sullivan began his three-year-old season in a mile race on January 30, 1958. In that race, two horses had been dueling for the lead: Circle Lea, ridden by Ray York, and The Shoe (by Khaled), ridden by Willie Shoemaker. When the tote board flashed a photo finish, York was sure he'd nosed out Shoemaker. "I beat you this time, Willie," said York. "Yeah," agreed Shoemaker, "but you didn't beat that sucker on the outside." Silky Sullivan had beaten them both by a neck. Later, he came from 32 lengths behind to lose by a neck to Old Pueblo in the $67,360 California Breeders' Champion Stakes. Eddie Arcaro (who rode Old Pueblo) said, "He's just a running fool. He runs that last eighth in 10 seconds flat—or less. You feel like you're standing still. Sometimes when he comes up alongside, you are."