Best known today as the betrayed manager of the infamous Black Sox, Gleason was a star player of the 1890s. He began as a pitcher with the Phillies. After two losing seasons, he blossomed with a 38-17 mark in 1890 when desertions to the Players’ League stripped the Phillies of their regular starters. He never approached that level again, although he twice more topped 20 wins. When the distance from the mound to the plate was increased in 1894, he lost his effectiveness.
A timely hitter and heady player, Gleason switched to second base, helping the Orioles win a pennant in 1895. He was traded the next year to the Giants, where he was named team captain. According to some reports, he was the first to order an intentional base on balls as a way to bypass a strong hitter. In 1897 he had his best offensive year, hitting .319 with 106 RBI. He jumped to the AL in 1901, then returned to the Phillies in 1903 for four more years as the regular second baseman. He stole 328 career bases.
After retiring as a player, he served first as a coach, then as the manager of the White Sox. Nicknamed Kid in part because he was 5’7″ but mostly for his enthusiasm, his heart was broken by his players’ sellout of the 1919 WS. He continued as manager of the crippled team through 1923, then became a coach for Connie Mack in Philadelphia.