Career
He played for the Saint Louis Browns, Baltimore Terrapins, Chicago Whales, Detroit Tigers, and Saint Louis Cardinals. He had a career record of 38–76 with a 3.57 earned run average. Despite his poor overall record, in the inaugural Federal League season of 1914, Bailey struck out more than one batter per inning (131 strikeouts in 1282⁄3 innings, or 92 strikeouts per 9 innings), a virtually unheard-of feat in that era.
In the 1910-1919 decade no other pitcher with at least 100 innings pitched even approached that level, with Rube Marquard (77 strikeouts per 9 innings in 1911) being second.
Nonetheless, Bailey had a losing record (7–9) in that season.