Howley broke in as a catcher with Indianapolis of the American Association in 1906 and appeared briefly with the Phillies in 1913. He managed at Montreal for four years, then moved to Toronto (International League), where he won a pennant in 1918. He was a coach for the Tigers in 1919 and 1921-22. He returned to Toronto, and in 1926 won a pennant to break Baltimore’s streak of seven straight flags. A combative manager known for his ability to develop young pitchers, he managed the Browns and Reds for three seasons each. In 1928 he brought the Browns in third, his best ML finish.