He was a four-time manager of the Toronto Maple Leafs of the International League, leading the team in 1918, 1923–1926, 1933, and 1937, winning the league pennant in 1918 and 1926. Howley was inducted into the International League Hall of Fame.\n', '

Prior to his managing career, Howley was a major league catcher for part of the 1913 season for the Philadelphia Phillies. He later served as a coach for the Detroit Tigers for three seasons, 1919 and 1921–22. Howley also acted as the first base umpire in a July 1922 game.\n', '

Howley died of a heart attack in his birthplace of Weymouth, Massachusetts at age 58.\n', '

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