In the 1966 Major League Baseball draft on June 7, Jackson was selected by the Kansas City Athletics. He was the second overall pick, behind 17-year-old catcher Steve Chilcott, who was taken by the New York Mets. According to Jackson, Winkles told him that the Mets did not select him because he had a white girlfriend. Winkles later denied the story, stating that he did not know the reason why Jackson was not drafted by the Mets. It was later confirmed by Joe McDonald that the Mets drafted Chilcott because of need, the person running the Mets at the time was George Weiss, so the true motive may never be known.