St. Gregory the Great was the first monk to be elected pope (Gregory I, 590 to 604 AD) and a great proponent of St. Benedict's monastic vision and avid promoter ofThe Rule. He was himself touched and moved by St. Benedict's words and by his followers and monks who resided in Rome following the first destruction of Montecassino. St. Gregory the Great was an extremely active and influential man himself during his lifetime, having been born right around the time that St. Benedict gave birth to The Rule.

Besides his great and numerous achievements in spreading St. Benedict's Rule and Christianity in Europe, he also authored the first biographical account of St. Benedict's life written between 593 and 594 AD. St. Gregory's Dialogues are a series of books about the lives of Italian Saints, abbots, deacons, nuns, bishops, and lastly aspects of the afterlife (heaven, hell and purgatory). The second of the four books is entirely about St. Benedict of Nursia. This biographical book has proven to be of immense importance in our understanding of not only St. Benedict's life but also of the beginnings of Montecassino. The book is divided into 38 chapters which speak about the numerous events and miracles that took place in his and St. Scholastica's lives, which St. Gregory explains were told to him by those closest to St. Benedict:

All the notable things and acts of his life I could not learn; but those few, which I mind now to report, I had by the relation of four of his disciples; namely, Constantinus, a most rare and reverent man, who was next Abbot after him; Valentinianus, who for many years had the charge of the Lateran Abbey; Simplicius, who was the third superior of his order; and lastly of Honoratus, who is now Abbot of that monastery in which he first began his holy life. (St. Gregory the Great, Prologue,Dialogues Book 2).