American sportswriter and baseball historian Lee Allen wrote that in 1903, Waddell was "sleeping in a firehouse at Camden, New Jersey, and ended it tending bar in a saloon in Wheeling, West Virginia. In between those events, he won 22 games for the Philadelphia Athletics, toured the nation in a melodrama called The Stain of Guilt, courted, married, and became separated from May Wynne Skinner of Lynn, Massachusetts, saved a woman from drowning, accidentally shot a friend through the hand, and was bitten by a lion."
It should be noted that Waddell was incapable of memorizing his lines for his part in The Stain of Guilt, so he was allowed to improvise his lines in every show. The play went on to critical acclaim.
In 1905, Waddell shared a room with baseball catcher Ossee Schreckengost who refused to continue sharing the room unless there was a clause in Waddell’s contract that forbade him from eating crackers in bed. It should be noted that it was common for players to share the same bed in hotel rooms while on the road. That same year, he missed the World Series after injuring his shoulder while trying to destroy a straw hat.
He did however, went on to win a Triple Crown in pitching. If the Cy Young award had existed during this time, Waddell would have won it over Cy Young himself.
Waddell never used the locker rooms and would come to the stadium in street clothes and strip down naked and change into his uniform for everyone to see. He then would proceed to grab drinks and hot dogs from spectators and down them before getting to the pitcher’s mound. He was so confident that he would occasionally tell his outfielders to vacate their positions and then proceed to strike out his opponents one by one. He would then cartwheel or somersault back to the dugout.