A St. Louis native, Gleason played amateur baseball for the St. Louis Stocks as early as age 16. He earned the nickname "Brudder Bill" because he was teammates with his older sibling, Jack Gleason, on several amateur and professional baseball teams. \n', '

Gleason entered the majors in 1882 with the St. Louis Browns, where he and Jack Gleason were the first siblings to play in the same major league infield. His most productive season came in 1887, when he posted career numbers in batting average (.288), runs (135), hits (172), and on-base percentage (.342). A member of three St. Louis champion teams from 1885 to 1887, in 1883 and 1885 he led the league in games played.\n', '

During his time with the St. Louis Browns, Gleason was roommates with Charlie Comiskey. While Gleason was considered a gentleman off the field, he was loud and aggressive on the baseball diamond, often hurling continuous insults at opposing players or using his spikes on the basepaths to break up double plays. An 1885 Sporting Life article suggested that if Gleason broke a limb or his neck, "not a ball player in the American Association would feel the slightest regret." \n', '

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