Rodríguez joined the army for two years when he was 19, and then after he was discharged he came back to Puerto Rico and worked as a caretaker on a psychiatric ward. Along the way, he kept improving his golf game, even winning a base championship at Fort Sill, Oklahoma, one year. In 1957 he was hired as head caddie at the Dorado Beach resort in Puerto Rico. A professional golfer named Pete Cooper, who had won ten events on the PGA Tour, was the course pro there, and he recognized Rodríguez's natural talent and worked with him to improve his game.
After three years under Cooper's tutelage, Rodríguez was ready to try the PGA Tour himself. In 1960 Laurance Rockefeller, who was, among other things, one of the owners of Dorado Beach, gave Rodríguez $12,000 to get started, and he and Cooper headed to Michigan to play in the 1960 Buick Open. To everyone's amazement, the newcomer was tied for the lead after the open's ninth hole. His performance slipped at the end and he did not win, but he finished in the money.
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