Gleason was born in Camden, New Jersey. He acquired the nickname "Kid" early in life, not only because of his short stature (growing to only 5-foot-7, 155 pounds) but also because of his energetic, youthful nature. Gleason played two seasons in the minor leagues of northern Pennsylvania. In 1886 at Williamsport of the Pennsylvania State League, he batted .355 and stole 20 bases in 36 games. Gleason debuted as a pitcher with the Philadelphia Phillies on April 20, 1888. He enjoyed several successful seasons, especially 1890 (38 wins), before becoming a second baseman. He was the starting second baseman for the old Baltimore Orioles in 1895. Gleason compiled a .261 career batting average before retiring after the 1912 season. With his two at-bats in one game in 1912, he became a member of the small group of men, 29 to date, who have played major league baseball in four decades.
Gleason in 1888
Gleason returned to the major leagues in 1912 as a coach, before becoming manager of the Chicago White Sox on December 31, 1918. In his first season, the team won the pennant but lost the World Series to the Cincinnati Reds, resulting in allegations that the White Sox had been paid by gamblers to "throw" the Series. The ensuing scandal resulted in lifetime bans from baseball for eight White Sox players. Gleason, however, was not involved in the gambling, and some sources note that he was among those who alerted White Sox owner Charles Comiskey of the fix. Although he felt betrayed and disappointed by his 1919 team, he continued to manage the White Sox until 1923.