Grimes played for the
Pittsburgh Pirates in 1916 and . In 1917, he lost 13 straight decisions. When the spitball was banned in 1920, he was named as one of 17 established pitchers who were allowed to continue to throw the pitch. According to
Baseball Digest, the
Phillies were able to hit him because they knew when he was throwing the spitter. He then pitched for the
New York Giants (), the Pirates again (–), the
Boston Braves () and the
St. Louis Cardinals (1930-). With the Pirates in 1928, he posted a 25–14 record, posting the most wins, complete games, shutouts, and innings pitched of any NL pitcher. He returned to the Cardinals in 1933 and , then moved to the Pirates (1934) and the
New York Yankees (1934). Grimes was nicknamed "Ol' Stubblebeard", related to his habit of not shaving on days in which he was going to pitch. Grimes was a very good hitting pitcher in his major league career, posting a .248
batting average (380-for-1535) with 157
runs, 62
doubles, 11
triples, 2
home runs and 168
RBI. He also drew 69
bases on balls. He had nine seasons with 10 or more RBIs, with a high of 16 in 1920 and 1928. In four World Series appearances (1920, 1930–1932) he hit .316 (6-for-19) with 1 run and 2 RBI. At the time of his retirement, he was the last player who was legally allowed to throw a spitball, as he was one of 17 spitballers permitted to throw the pitch after it was otherwise outlawed in 1920. Baseball historian Frank Russo called him "baseball's most aggressive spitballer". Then, on his first pitch, he knocked down a Giant. He is listed in the
Baseball Hall of Shame series for having thrown a ball at the batter in the on-deck circle. The only two batters Grimes apparently could not intimidate were Hall of Famers
Frankie Frisch and
Paul Waner. If Grimes threw a close pitch to them, the batters usually followed it up with a hard-hit
line drive. ==Post-playing career==