Drill was born in Browerville, Minnesota, in 1877. He attended Georgetown University in Washington, D.C., and Hamline University in St. Paul, Minnesota. He was the catcher for the Georgetown baseball team.\n', '

Drill began his professional baseball career in 1902 as a catcher for the Washington Senators and Baltimore Orioles. He compiled a .262 batting average in 73 games during the 1902 season. He returned to the Senators in 1903 and 1904.\n', '

Drill joined the Detroit Tigers in July 1904. During the 1904 and 1905 seasons, he appeared in 123 games for the Tigers and compiled a .253 batting average and a .353 on-base percentage.\n', '

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