Conroy picked up the nickname “Widow” for his solicitous concern for younger boys on his sandlot team and was known as “Wid” all his long life in organized baseball. He began 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 was the first-string shortstop of the NL champion 1902 Pirates, but became a third baseman when he returned to the AL with the Highlanders (later the Yankees) in 1903. He led AL third basemen twice in total chances per game. His 22-year career in pro baseball ended as a Phillies coach in 1922.
