- "Blessings on you, brother."
- ―Darby to Ezio after being rescued, 1488.[src]
Born "beyond the Pale" (or the portion of Ireland outside English control), Darby spent his teenage years hunting and raiding English settlements. In his papers, he described the time period as "a dark point in my life, but, to be honest, I had my fun too".
Becoming a monk
When Darby'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", Darby once wrote in 1462. To escape his father, Darby decided to become a monk, encouraged by the fact that he was told by his mother that monks "did little work, and threw large feasts for the seasonal holidays."
Darby joined the Abbeylara Monastery in 1462, and became a Cistercian. Ultimately, however, he found the Order too austere: "We worked in the fields from dawn until dusk, Abbot 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, Darby 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 claimed 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."
Monastery in Romagna
Darby moved to the Romagna countryside in 1494, starting a monastery dedicated to the Order of St. Patrick in an abandoned church. However, he did not have much success in securing converts.
Probably during the same year or shortly after, Darby was attacked by a group of soldiers. Luckily for him, Ezio Auditore da Firenze was nearby and saved him from his attackers. Ezio asked him if he knew of a monk with a missing finger, to which Darby recalled seeing the man in the abbey of Forlì.
In 1500, Darby died from what was described to be "bad blood", but was most likely syphilis. His body was buried in the small cemetery beside his church.
- "O'Callahan" is an anglicized version of the Irish name "Ó Ceileacháin", which means "descendant of Ceallacán".