[3] Douglas originally signed with the Chicago White Sox in 1912, but soon landed with the Cincinnati Reds.

Douglas' short stints with these and future teams stemmed from their frustrations with his well-documented alcoholism,[4] about which a contemporary journalist wrote, "Drinking was not a habit with Douglas—it was a disease.

"[3] His throwing error on a sacrifice bunt in Game 4 of the 1918 World Series gave the Boston Red Sox a 3–2 victory over the Cubs.

Following the season, the spitball was banned but 17 players, including Douglas, were allowed to continue using the pitch.

Shortly after he was suspended and while intoxicated,[5] Douglas sent the following letter to Les Mann of the St. Louis Cardinals: I want to leave here but I want some inducement.