Sold at the 1956 California Thoroughbred Breeders Association's Del Mar yearling sales to Phil Klipstein (a retired cattleman from Bakersfield) and Tom Ross (a lumberman from Oakland) for $10,700, the colt was sent to Devonshire Downs in San Fernando to train under Reggie Cornell. Silky Sullivan's first race was a 5 furlong dash for maidens at Hollywood Park Racetrack on May 17, 1957. Cornell said, "He came out of the gate in a trance and a truss and I said, here's one for the glue factory. Then all of a sudden, it was like he was stung by a bee. Until he made that big move, I thought I'd be looking for a job." His jockey, George Taniguchi, said, "He broke with the field and then it was as if he was sucked back, and I thought oh, my God, what's he doing? He was immediately 10 or 20 lengths behind the other horses. I let him go like that until the three-eighths pole and finally gave him a tap on the shoulder, and then he changed gears. I never thought we'd catch up, we were so far back, but I never rode anything like that before. We were flying." In his debut, Silky Sullivan was 8th in a field of 12 and about 8 lengths back, when he came on to win by a nose.