Gleason was born in Camden, New Jersey. He acquired the nickname "Kid" early in life, not only because of his short stature but also because of his energetic, youthful nature. Gleason debuted as a pitcher with the Philadelphia Phillies on April 20, 1888. He enjoyed several successful seasons, especially 1891 (38 wins), before becoming a second baseman. Gleason achieved a .261 career batting average before retiring after the 1912 season. He is one of several players to have appeared in a major league game in 4 different decades. He began his career as a manager with the White Sox on December 31, 1918.