For the first two years of his career, Jackson had some trouble adjusting to life with the Athletics; reports conflict as to whether he just did not like the big city, or if he was bothered by hazing from teammates. Consequently, he spent a great portion of that time in the minor leagues. Between 1908 and 1909, Jackson appeared in just 10 MLB games. During the 1909 season, Jackson played 118 games for the South Atlantic League's Savannah Indians. He batted .358 for the year.