Nicknamed "Ol' Stubblebeard", Grimes was born in Emerald, Wisconsin. He made his major league debut on September 10, 1916 for the Pittsburgh Pirates and in 1920, when the spitball was banned, he was named as one of the 17 established pitchers who would be allowed to continue to throw the pitch. The 26 year old Grimes made the most of this advantage, and over the course of his 19-year career, won 270 games and pitched in four World Series. At the time of his retirement, he was the last of the 17 spitballers left in the league.
Template:MLB HoF He played for the Pittsburgh Pirates (1916 - 1917), the Brooklyn Dodgers (1918-1926), the New York Giants (1927), the Pirates again (1928-1929), the Boston Braves (1930), the St. Louis Cardinals (the rest of 1930 and 1931), the Chicago Cubs (1932 and part of 1933), the Cardinals again (the rest of 1933 and part of 1934), the Pirates again (1934), and the New York Yankees (the last part of 1934).
He was the manager of the Dodgers in 1937-38, compiling a two-year record of 131-171 (.434), with his teams finishing sixth and seventh respectively in the National League. He then remained in baseball for many years as a minor league manager and a scout.
He died in Clear Lake, Wisconsin at age of 92.
- Grimes was well-known for his mean temper. He was so mean, he once threw a ball at the batter in the on-deck circle.