Shoemaker had his first win on April 20, 1949 riding Shafter V at Golden Gate Fields. In his first full year, he had an impressive 219 winners. And before long, he was predicted to be a perennial winner. In a 1953 Newsweek article jockey Ted Atkinson remarked, "This is a real race rider.… He will go on and on." What observers like Atkinson saw was a quiet rider with gentle hands, someone who used smarts to win his races. A Newsweek writer explained, "They attribute to him an excellent sense of pace, an eye for a developing pattern of danger that can be avoided up ahead, and a way of first hustling his horse out of the gate and then letting the animal settle into his stride pretty much on his own until the rider feels the mechanism under him to be functioning smoothly." Nearly a decade later, the accomplished jockey Eddie Arcaro complimented him in Time, saying, "Willie takes such light hold of a horse … that he could probably ride with silk threads for reins."
Quiet in the saddle, Shoemaker was also quiet when interviewed, although after decades in the media spotlight, he learned to be more communicative. In 1950 a Newsweek writer described him as someone who "can make a whole conversation out of a nod." At the time he was battling Italian rider Joe Culmone for the year's most wins, but when asked to identify the best jockey, he said "Eddie Arcaro." The jockey was never one to boast about his accomplishments. Shoemaker and Arcaro would in fact become good friends and Shoemaker would credit the other jockey with teaching him to relax and work with the horse rather than resort to the whip. In 1999, Shoemaker was eloquent in his appreciation of another jockey, when Laffit Pincay passed his record 8,833 career wins. He said in an interview for cbs.sportsline.com, "There has never been anyone more dedicated to their profession or sport like Pincay. To have my record broken by him is a very big honor."