Born in Boston, Pennsylvania, Douglass was raised in Wellsville, Missouri. He played independent baseball in Missouri before ascending to professional baseball. Douglass played in the minor leagues only briefly, appearing as a player-manager for the 1895 Sherman Orphans of the Texas-Southern League.
Douglass was a left fielder when he debuted for the St. Louis Browns in 1896, but he registered a fielding percentage of only .894, and the team moved him to catcher the next season. Douglass was sent to Philadelphia in a multiplayer trade before the 1898 season, and he became the team's first baseman. Promising infielder Nap Lajoie has been the team’s primary first baseman, and Lajoie was shifted to second base. Lajoie stayed at second for the rest of his career and became a Baseball Hall of Fame inductee. Douglass had his best offensive season in 1898, hitting .258 with 105 runs scored. He spent the rest of his career at catcher or first base.
Klondike last appeared in the major leagues in 1904, and he played in the minor leagues until 1912. He died at the age of 81 in Bend, Oregon.

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