Gregg started his professional career in Portland, Oregon in 1910 with the Pacific Coast League. He threw 14 shutouts.\n', '

The next year, he played for the Cleveland Naps, going 23–7 with a league leading 1.80 ERA. In 1912 and 1913, he started 34 games both years with an identical 20–13 record each season.\n', '

Gregg was traded to the Boston Red Sox in mid-1914. He played for them on both the 1915 and 1916 World Series championship teams. He developed a sore arm in 1914 and had continual arm problems for the rest of his career.\n', '

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