Ossie Vitt was a product of the sandlots of San Francisco. He broke into the Pacific Coast League as third baseman for the Seals in 1911. He later advanced to the majors as a utility infielder for the Detroit Tigers. As the Tigers' regular third baseman from 1915 through 1917, he never batted higher than .254. But he was described as a smart, scrappy baseball man.

After playing in the majors for 10 years, Vitt was recommended to Oaks' owner Victor Devincinzi by the Yankees' management to manage the Oaks in 1935. His upbeat style was described as both abrasive and motivational, pushing the Oaks to a third place finish.

Vitt moved on in the Yankees' organization the next year, managing their farm team in Newark. He was then hired by the Cleveland Indians in 1938 to replace Steve O'Neil as manager and instill new life into their team. The team finished third in 1938 and 1939, but Vitt's management style was resisted by the players. They unsuccessfully petitioned for his removal in 1940, and became known as the Cleveland Crybabies. Their bickering eventually lost them the pennant they had been expected to win, finishing a game behind the first place Tigers.