Fletcher was associated with two New York City baseball dynasties: the Giants of John McGraw as a player; and the Yankees of Miller Huggins and Joe McCarthy as a coach.

Born in Collinsville, Illinois, he batted and threw right-handed, stood 5 feet 10 inches (1.78 m) tall and weighed 170 pounds (77 kg).

Traded to the Philadelphia Phillies in the midst of the 1920 season, he retired after the 1922 campaign with 1,534 hits, 32 home runs, 676 RBI and a .277 batting average.

Fletcher then began a 19-year tenure (1927–1945) as a coach for the Yankees, where, beginning with the legendary 1927 team, he would participate on ten American League pennant winners and nine World Series champions.

On a tragic note, he served as the acting manager of Yankees for the last 11 games of the 1929 season when Huggins, 50, was fatally stricken with erysipelas and pyaemia.