Dillon was born in 1873 in Normal, Illinois. His father, Levi Dillon, owned a business breeding and selling Percheron horses. Dillon attended the University of Wisconsin and played for the Wisconsin Badgers baseball team from 1892 to 1894. Dillon was a cousin of Hall of Famer Clark Griffith.\n', '

In 1894, Dillon figuratively worked both sides of the temperance movement by playing professional baseball for both the Peoria Distillers and the Des Moines Prohibitionists of the Western Association. Over the next four years, he played for Ottumwa in the Eastern Iowa League, Bloomington in the Western Interstate League, Dubuque, Rockford and Rock Island in the Western Association, Scranton in the Atlantic League, and Buffalo in the Western League.\n', '

In 1899, Dillon made his major league debut with the Pittsburgh Pirates. He appeared in 30 games as a first baseman for the 1899 Pirates and compiled a .256 batting average in 121 at bats. He returned to the Pirates in 1900, but appeared in only five games.\n', '

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