In , Ormsby started his umpiring career in the Illinois–Indiana–Iowa League. He moved on to the Western League in , before being hired by the American League in . In 1927, he required a police escort from the field in Philadelphia after a foul ball ruling on a blast hit by Ty Cobb. Fans rioted after Cobb and Al Simmons were both ejected from the game. At a 1929 Philadelphia-Cleveland game, Ormsby sustained a concussion when was hit in the head by a glass bottle intended for another umpire.
