Born beyond the Pale (outside the area of British control in Ireland, which was considered savage, hence, the expression "beyond the pale"), Darby O'Callahan spent his teen years hunting and raiding British settlements. In his papers, he describes the time period as "a dark point in my life, but to be honest, I had my fun too". O'Callahan moved to the Romagna countryside in 1494, starting a monastery dedicated to the Order of St. Patrick in an abandoned church, but he didn't have much success in securing converts.