Date of Birth: 1452.
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".
When O'Callahan's Gaelic father married a Catholic, everything changed. "He forced me to work the fields. No more raiding, no more girls. It was Hell on Earth", says one particular entry, dated 1462. To escape his father, O'Callahan decided to become a monk: "I was told by my mother that monks did little work, and threw large feasts for the seasonal holidays".
He joined the Abbeylara Monastery in 1462, becoming a Cistercian. Ultimately, however, O'Callahan found the order too austere: "We worked in the fields from dawn until dusk, Abbott Shaw wouldn't allow us to drink, and worst of all, the only girls were nuns. This was a deeper level of Hell than I had ever imagined possible".
Convincing a small group of his fellow monks to join the Dominicans, Darby left Ireland in 1463 for Italy: "where we can hire farmers to work for us in the fields. Then, when we give our sermons, we will see the beauty of the Lord in the golden light of Italy and the soulful faces of the farmer's wives".
Ultimately, O'Callahan was kicked out of the Dominican order in 1493, due to "repeated attempts to convert townspeople while within a drinking house". In Darby's own accounts he claims that he had great success with the conversions, although the men "refused to come to church, so I had to return to the ale house for repeat visits to preach the word of the Lord to their receptive ears".
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.
In 1500, he died of what had been described as "bad blood", but was most likely syphilis. His body was buried in the small cemetery beside the church.