Orphaned at twelve by a cholera epidemic that took his parents, Dixon was placed in an orphanage in Olathe Kansas. He promptly escaped and began a life of petty crime to survive.
By fifteen he was a shrewd and cunning criminal known for petty theft, breaking and entering, burglary, and pickpocketing as he moved his way east to New York where his talents were quickly recognized by elements of the Irish, Jewish and Italian syndicates. Having no prejudices, he did business with all three.
He missed the conscription for World War I with a medical deferment.
He crossed paths with O'Rourke on several occasions but did not actually get to know him until both were in Florida.