St. Gregory the Great (c. 540-604) was Bishop of Rome from 590-604. The son of St. Silvia and Gordianus, a Roman patrician, he was appointed urban prefect of Rome in 573 and entered monastic life the following year. Upon his father’s death, he converted the family’s Roman villa on the Caelian Hill into the Monastery of St. Andrew, where today there is still a monastery and the Church of St. Gregory on the Caelian Hill. At that same monastery he set the precedent for the Gregorian series of Masses: the practice of having thirty Masses offered for a deceased person. In 579, Pope Pelagius II made him a deacon and sent him as papal ambassador to the imperial court in Constantinople. In 590, a few years after his return to Rome, Gregory was elected Pope. One of his most important actions as Bishop of Rome was to appoint the prior of the Monastery of St. Andrew, Augustine of Canterbury, as the head of a mission to convert the English. Through his writings, he exerted an immense influence of spirituality and ministry in the Latin Church throughout the Middle Ages and was recognised as a Doctor of the Church.

In this interview, Dr. Thomas Humphries will explain his pick of the five best books by St. Gregory the Great.

Dr. Thomas Humphries is Professor in the College of Arts and Science at Saint Leo University, Florida. A native of Arkansas and a life-long Roman Catholic, he holds a mandatum from the diocese of St. Petersburg and enjoys giving regular theological reflections outside of the classroom with student faith communities, parishes, and monasteries. He also volunteers with the local fire department as Chaplain and holds the rank of District Chief. He is a licensed Florida EMT and NREMT. He is the author of Ascetic Pneumatology from John Cassian to Gregory the Great (Oxford University Press) and Who is Chosen? (Wipf and Stock).

  1. Forty Gospel Homilies
    by Gregory the Great
  2. Moral Reflections on the Book of Job (6 vols.)
    (vol. 1) (vol. 2) (vol. 3) (vol. 4) (vol. 5) (vol. 6)
    by Gregory the Great
  3. Homilies on the Book of the Prophet Ezekiel
    by Gregory the Great
  4. On the Song of Songs
    by Gregory the Great
  5. The Life of St. Benedict by Gregory the Great: Translation and Commentary
    by Terence G. Kardong OSB
Five Books for Catholics may receive a commission from qualifyng purchases made using the affliate links to the books listed in this post.

To kick off, what would you add to the preceding biographical sketch of St. Gregory the Great?
My goodness, you remembered many wonderful details. We need to interpret those details to be sure that we understand the meaning of the life of the saint.

Think of someone like Gregory donating his property to be a monk. That was a relatively common thing among wealthy men who were looking to retire. One of the tricks in the era was to donate the property to the church, call it a monastery, and then name yourself as the superior of the monastery. It was a way to play both ends. These people wanted to be a monk, holy, and pursue a life of virtue, but they did not want to start at the bottom of the ladder. Gregory does exactly the opposite. He says, “If I am going to donate this property and become a monk, then I need to live under obedience to someone else.” So, he does not name himself superior of his own community. He subjects himself to formation. What a wonderful lesson in humility. It is an example of how to truly embrace a life of holiness and admit that we are all children of God and in need of formation from the Church. Gregory did not know that he would earn the title ‘the Great’ by popular acclamation. But you see why he is “the Great” right there. There is his humility. Similarly, if we just want to take a lesson in like secular history, there is a lot going on that shows why Gregory is a fantastic leader and everybody was clamouring after him to be their leader. He knows that he needs to earn his spot and pay his dues. He needs to start and learn everything from the bottom up.

We see this over and over in Gregory's life. He is committed to the work that needs to be done. For this reason, he resists being made one of the seven deacons of Rome. That was not the same position as that of the deacon of a parish today. There was not necessarily any ordination. It is the position out of which the college of cardinals developed: the clergy of Rome, who conduct important Roman business worldwide. Gregory was reluctant to go to Constantinople. He essentially refused to be the Pope's designee there unless the Pope would also send some of his monks with him. He knew that he needed community, to be a part of that life of virtue and holiness. Gregory really stands out for his humility.

Gregory knows that in every letter of Scripture, he can find multiple layers of meaning.

Why is St. Gregory the Great worth reading today?
Some people are simply interested in historical figures. It is not just the time or the details that draws them to these figures, but their whole personality. Gregory was the second pope to earn the civil accolade of “the Great”. Think of Constantine the Great. What does it take for Western history to hail you with that title, magnus? A few generations earlier, St. Leo was the first pope to earn that title. Gregory is the second. If you are interested in historical figures and want to read someone who did many wonderful things, pick somebody who has that title. It might as well be Gregory.

In terms of specific things that are going on today. Gregory has an incredible call to the struggle of the present life. He lived at a time in history when things were changing. Historians debate when one era ends and the next begins. When did antiquity end? When did the mediaeval period begin? What is Byzantine? What is not? These are difficult questions but there is no doubt about that Gregory is at a cusp. He is on that edge. There is a lot of turbulence at the edge, but many profound things are also taking place. Gregory gives us incredible lessons on how to navigate all that turbulence. Maybe every generation feels like it is in turbulence and that it is at the dawn of a new age. We see the old generation go out and the new come in. Everyone faces this and it is how we feel today. Many things are going on whose consequences surpass anything we can understand. We can take solace in Gregory’s ability to acknowledge the struggle and to carry on. He admits to something that is difficult for us to hear, but which we need to hear. Despite the incredible goodness we find in this life, and in the face of incredible evil and atrocity, this life is not the one for which we are intended. Gregory reminds us—and sometimes he even scolds us—that we should not place all our hope in things that pass. We need to pay careful attention to the times, read the signs, and learn how to live in the world as a servant of the servants of God. We need to recognise that all of this is, ultimately, rooted in God and headed towards him. Sometimes, this life is wonderful. Sometimes, it is sometimes difficult. Regardless, it is not the life that we intend, want—and for Gregory at least—for which we hope.

Often, allegorical commentary is not understood at all or misunderstood.

In one way or another, each of St. Gregory’s works boils down to biblical commentary or, as befits a monk, a lectio divina. Modern readers may find it difficulty to follow his train of thought or appreciate his insistence on the allegorical sense of biblical passages. Do you have any tips for reading him?
I do! I am glad that you brought up the lectio divina, which has seen a renewal over the last thirty years. There is lots of literature out there. You can find YouTube videos on it and dozens of books on Amazon.

Often, allegorical commentary is not understood at all or misunderstood. At the opening of several of his commentaries, as in The Song of Songs or Moralia in Iob, or just when he is commenting on a particular text, Gregory is very clear that he is aware of questions of authorship and the text’s history. But this is not the important thing. What we are looking at in this text is the life of one who was guided by the Holy Spirit. We are looking at a holy man or woman who lived in such a way as to be perfectly permeable to God's action. We read Scripture, Gregory says, not simply to learn historical details. They are important but constitute the first level. The real reason we read Scripture is to encounter the Word of God, the second person of the Trinity: to encounter Christ in the words on the page. The real reason we want to read an inspired text, which tells us about other inspired humans, is to come into contact with the Holy Spirit and become holy, inspired people

You can think of Ezekiel as just a book in which one of the prophets wrote down his thoughts. Gregory pushes back against this. You are reading Ezekiel's thoughts, but they are important because they are God's thoughts. It is God who has worked in Ezekiel's life to allow him to see this truth. You want to learn not just how Ezekiel felt or what he said, but to become a prophet. You read the prophets to become a prophet yourself. It is the same as participating in the sacraments. We do not go to the Eucharist simply to write a beautiful philosophical exposition on how God can be present. That is important work. But we go to the Eucharist to be nourished by Christ. When we open Scripture, we want to encounter not just the text, but the Word. Pope Benedict XVI summarised this very well. He said that Christians are not a people of the book. We are a people of the Word, the second person of the Trinity, the Son of God, the Word who became flesh.

Now, Gregory knows that in every letter of Scripture, he can find multiple layers of meaning. We need to be open, with our memory and mind, to see Gregory make more than one interpretation of an event. God was working in Job’s life. His action does not mean just one thing.

Gregory is challenged by his fellow monks to interpret the Book of Job. It is a very difficult book about suffering and pain. Job seems to be a righteous man, but one whom God leaves to be tempted by the devil. What is going on? The monks know that Gregory is skilled at biblical interpretation and ask him to provide one. He gives not one but three interpretations of every verse. He tells them what it means in the historical or literal sense; then in an allegorical sense; then in a moral sense. There is a lot going on here.

For example, Job has seven sons and three daughters. In the literal or historical sense, he has ten children: a big family. Gregory reflects on what it means to have a big family and Job’s status.

Then there is the allegorical sense. Take the seven sons. How do you get 7? By adding 4 and 3, an even and an odd number, which is indicative of a certain tension. That makes us think about 4 × 3=12. The reason that God has Job and his wife have seven sons is to be a type of the twelve tribes of Israel, the twelve apostles, and the Church. Why do they have three daughters? Because there are three ranks or orders in the Church: the preachers (clergy), the celibates (nuns and monks), and the married. So, Job’s family is a complete depiction of the Church. It points to the Church and tells us something about its structure.

Then there is the moral meaning. There are seven virtues: the four cardinal and the three theological virtues. Why are there three daughters? God wants to highlight faith, hope, and love as particularly distinct. Then the seven sons refer to the gifts of the Spirit and the ten children to his fruits.

So Job’s life family can have multiple meanings. If you would like to have one thesis and argue tooth and nail that your interpretation is correct and my interpretation is wrong, then you are not doing what Gregory is doing. You have closed yourself to the multiple layers of meaning in Scripture.

One other point. Sometimes these interpretations strike us as awkward. Could not the passage mean anything? What are the limits on a moral or allegorical interpretation, or the historical interpretation for that matter? The limits are the truth and inspiration we have as we pray, reading Scripture divinely or for the divine (lectio divina). Here we can think of how our own lives have meaning.

My name is Thomas Humphries Jr. By meeting me, you already know that there is a Thomas Humphrey Sr. My very existence or presence signifies something about other humans. You know about my mother, even though you do not know her name yet. In seeing any child, you know something about that child's parents and history. It is not just the words that I speak, but my very presence, that tells you that there is a man and a woman who loved each other and, decades ago, raised a child. In other words, at a regular level our lives have multiple layers of meaning. The lives of the holy men and women recounted in Scripture have multiple layers of meaning too.


Why is St. Gregory’s collection of Forty Homilies on the Gospel your first recommended book? This is not his best-known work.
I thought a lot about which book I would put first. There is an issue of practicality. If you are Catholic, you may want to read a commentary on Scripture, but there are a zillion different things out there. This is confusing and frustrating.

Moreover, often think, “Well, that was a smart interpretation, but is it right? Is it going to lead me to a virtuous life and draw me closer to God?” People want to study the Scriptures and, for Catholics, they do not come to us simply as a bible that sits on the shelf, that we open, and then read as an object of study. They come to us in the liturgy. The lectionary makes Scripture come alive. That was certainly my experience. Long before I opened a Bible and learned to study it, I was hearing the Scriptures proclaimed at Mass and preached, somewhat like these forty homilies on the Gospel.

This is a collection of some of Gregory's best homilies. They are organised according to the gospel that was that was prescribed in the lectionary. The lectionary changes, but many of these passages are still the same. The reading for Christmas is still the same. The reading for the Ascension is still the same. The passages that we use to celebrate the Virgin, martyrs, saints, or doctors do not change. So, you can pick up the Gospel Homilies and work through the liturgical year. Read Gregory's homily on Pentecost to prepare for Pentecost or right after Pentecost. This is the practical value of Forty Gospel Homilies. There are fifty-two weeks in a year. You can read one a week and make your way through the liturgical year. It will help you engage Scripture in a truly Catholic and liturgical way.

Those homilies are profound. Take Gregory's interpretation of Pentecost and the tongues of flame. Why does the Spirit sometimes appear as a dove and sometimes as a tongue of fire. Here is a problem that we need to think about. Why does God choose to manifest himself in different ways? The fire comes because it is a consuming fire, just as in our prayer and virtue we should be totally consumed with God. The Spirit comes as a tongue because it is by a tongue that one speaks the Word. You can never separate the Son from the Spirit. You get this this back and forth in which Gregory does profound theology, clarifying the Trinity, the relationship between the Word and the Spirit, and between Pentecost and what it might mean for me. How could I learn to speak with a tongue of fire, with an anointed tongue, with the Holy Spirit within me? As I said, the homilies are practical, beautiful, and there is always something surprising to see in Gregory’s interpretation.

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