Caldwell was notorious during his playing career for his addiction to alcohol and partying; he possessed a self-destructive streak that many of his contemporaries believed stopped him from reaching his potential. In 1924, Miller Huggins wrote: 'Caldwell was one of the best pitchers that ever lived, but he was one of those characters that keep a manager in a constant worry. If he had possessed a sense of responsibility and balance, Ray Caldwell would have gone down in history as one of the greatest of all pitchers.'[2] Yet, despite his achievements on the field and his antics off it, Caldwell is perhaps best remembered for being struck by lightning whilst playing for the Cleveland Indians against the Philadelphia Athletics in 1919; remarkably, despite being knocked unconscious, he refused to leave the game, having pitched 8.2 innings, and went on to record the final out for the win. After the game, he had a serious concussion, but still decided to go out and smoke opium with prostitutes. He ended up marrying that same prostitute that he met that night, where he conceived four boys Greg, Adam, Colin and Samuel Caldwell.
Guy was an absolute gangster.