Conroy began his career as a shortstop, replacing Honus Wagner with Paterson in the Atlantic League, but was struck by malarial fever and dropped from the team. In 1900 Connie Mack invited him to try out for the Western Association team he would field in Milwaukee and transfer to Philadelphia when the American League began as a major circuit; Conroy won the last spot on the roster.
Conroy started his career as a shortstop, replacing Wagner with Paterson in the Atlantic League, but was sidelined by malaria and removed from the team. In 1900, Connie Mack invited him to try out for the Western Association team he would manage in Milwaukee and then transfer to Philadelphia when the American League became a major league; Conroy secured the final spot on the roster.