Again, notes from my talk to the RCIA on the history of the Church:
There were high points and low during these years (the early Middle Ages). Arguably, the greatest Pope ever, Gregory the Great, reigned from 590-604 and provides a link between monasticism and the greater Church for he had been a monk on the Coelian Hill where his church still stands today. He used the resources of the Church, which had become the largest landowner in Europe, to feed the poor throughout disintegrating imperial lands. This, in turn, gave him leverage to appoint Roman-trained clerics to bishoprics in preference to locally grown, but often incompetent or unholy or both, candidates, and his candidates carried out reforms like his own to eliminate corruption and improve care for the poor and the administration of good works. Gregory wrote extensively about the nature of leadership in the Church, instructing bishops to ground their authority in service. The title he applied to himself – Servus servorum dei – has returned to its primacy in the long line of papal titles. He was suspicious of the Eastern notions of Episcopal authority which he thought were too tied up with political ideas as, indeed, Caesaro-papism was already firmly rooted in the eastern churches. Gregory also was a great evangelist, the first Pope to see the need to evangelize beyond the empire. He ordered his agents in Gaul to buy English slave boys to be trained in Roman monasteries and dispatched them, under the leadership of Augustine (not the one from Hippo) to convert England. Augustine set up his monastery at Canterbury which was the primatial seat of Christianity in Britain until the Reformation when the heretofore outstanding loyalty of the English Church to Rome was cast aside.