A native of New Orleans, Louisiana, who broke into baseball as pitcher, Gilbert first became famous as a member of the 1914 "Miracle" Boston Braves.

[1] The team then went on to defeat Connie Mack's heavily favored Philadelphia Athletics in the 1914 World Series.

In his lone appearance in the series, Gilbert drew an intentional walk off Bullet Joe Bush as a pinch hitter in Game 3, played at Fenway Park.

[2] Gilbert became more famous as a minor league manager in the Southern Association, where he led teams for 25 seasons, including the New Orleans Pelicans from 1923 to 1931 and 1933–38 and the Nashville Vols from 1939 to 1948.

Gilbert won eight Southern Association championships during his quarter-century in the league, including six consecutive titles (1939–44) with the Vols.