The Dialogues, downloadable for free in non-antiquated English here, was written by request of members of his Papal household. Structured as a conversation between Gregory and his deacon Peter, Dialogues tells miracle stories of contemporaneous (so, end of the 500s) saints of Italy. In addition to encouraging his readers that holiness is alive and well in contemporary Italy, not just far away and long ago, he also gives commentary via Peter’s convenient questions that directs the reader toward holiness via poverty, chastity, and almsgiving, and even some hell-fire stories at the end. To give some flavor, I shall continue this as a discussion with a fictional younger brother, Paul.

Paul I appreciate you taking the time to summarize this historic book for me.
Geoff   What could I do, Paul, when you asked so earnestly, except do my best for your edification? But it is no hardship, because, as you well know, the teacher learns more than the student, and in any case, it is my habit to write summary reviews for all the books I read so as to have their contents available for easy reference. As it happens, their primary use is informing others, since the process of writing them solidifies the contents in my mind.
Paul So what are the primary features of the Dialogues?
Geoff Clearly the primary focus is miracle stories of Italian holy men, but there is a strong didactic element too.
Paul I would really like to hear some of the stories
Geoff Well, to be honest, after maybe one hundred stories from dozens of people, they all sort of blend together. A large number of them are abbots who had no food for those under their care, and received miraculous food, or multiplied food. One abbot, after praying, went to the community ovens and found one loaf of white bread left. He took it, and asked around all the houses, but everyone said that they had already got their bread, so he kept it and fed the construction workers with it, and the leftovers kept multiplying for a week. Another monk went to some Lombards (a people who had cruelly pillaged the land) who were unsuccessfully trying to press olive oil and demanded that they fill his oilskin. They laughed at him, whereupon he poured some water into the press, and oil came out. After that they had no difficulty pressing the olives. Quite frequently the abbot has complete confidence that God is going to provide, so just he tells the monks to do whatever it is—despite their doubts—and it happens.

There are some other stories of need, such as one kid who had fallen into the river, and St. Benedict told one of the monks to get the child, so he ran out and did not realize that he ran out past the land. He ran on the river, grabbed the child, and ran back before he realized what he had done. Similarly, a woman had borrowed a serving tray in some connection with serving the abbot or a visiting priest, but dropped it and it broke. She had no money to replace it, so the saint knelt over it prayed (with tears, if I recall correctly), and when he opened his eyes, the cracks in the tray had been repaired. The townspeople put it over the door of their church.

Gregory draws the conclusion from these stories, or at least states, that miracles are evidence of holiness.
Paul That certainly seems reasonable.
Geoff
Perhaps, but I think that Gegory forgot that our Savior related that “some will say to me, ‘Lord, Lord, did we do miracles in your name?’ but I will say to them ‘Away from me; I never knew you’”. Likewise, even in our day there are some who did amazing miracles but later fell into grievous sin—and I am in no way saying that these did not or do not know Jesus. Todd Bentley headed a healing revival for a few years, but divorced his wife and married his secretary. So I do not think miracles are not evidence of holiness. But the famous miracle-workers of the last century do consistently with spend hours with God, in prayer, in Bible reading, and in worship. Smith Wigglesworth, British plumber and healer, would frequently excuse himself from the dinner at his hosts because he felt God calling for him and, if I understand correctly, would spend the rest of the night in his room. Todd Bentley spent at least three hours a day “soaking in God’s Presence”, at least prior to the revival. William Seymour, who was instrumental in starting the Azuza Street revival, spent months seeking the baptism of the Spirit and speaking in tongues, and spent hours at the church during the revival meetings (with his head in a box, I think for humility). The young man who led the Welsh Revival spent something like four hours a day praying.
Paul Is there anything we can say about miracles?
Geoff Well, most of the miracle stories that Gregory relates have in common that some person or group of people have a need that they are not able meet, and the man prays, sometimes with tears, and asks God to provide. In a few cases, the person tells them what to do, like prophets like Elisha did. Gregory says that this illustrates that sometimes the saints perform miracles from their own power, sometimes the miracle is from someone else’s power (such as one where a sandal of a dead saint heals someone), but most of them happen through prayer.
Paul These are very incredible stories! It seems difficult to view them as credible, though, especially since some of them are very close to stories in the Bible. Do you think they are believable?
Geoff Gregory goes to some effort to source these stories. He only tells stories that were told to him by people who knew the person and who he trusted and who are known to be holy and trustwrothy. In some cases he knew the person himself. He gives the name of the person, the person who told him, and the location where it took place. In some cases he can even give a time frame.
Paul Are there other types of miracle stories that he relates?
Geoff Certainly! During Greogry’s time the Lombards were ravaging Italy, and frequently enslaved people. One abbot, I believe, saw a monk or a townsman taken captive and, imitating Christ, offered to sell himself into slavery with the price that the other man be set free. The Lombard agreed, and the abbot ended up providing herbs (I assume this meant vegetables) for the table of a man in northern Africa. He worked well, and the man commended him to the local king. He provided some prophetic service to the king, who then asked how he could repay him. The man said that he could repay him by setting all his countrymen free, which he did, and they sailed back to Italy. (The king died a day or two later.) There are also a bunch of stories about the Lombards insisting that the abbot give up his gold (which he didn’t have, because if he did he would have given it to the poor), and either some miracle happens to the Lombard, like his feet sticking to spot, or they miraculously avoid the Lombards. Usually the miracle ends up with the Lombards changing from contempt to respect for the man’s holiness. One Lombard king tested a blind bishop’s prophetic reputation, by inviting the bishop to a meal and having someone claim to be him and serve the bishop wine; the bishop immediately “saw” right through it. There was one where the Lombards, who were Arian, mock a church or try to ransack it, and the church is filled so full of light that no one can enter. There was another one, not related to the Lombards, where the town flooded and the water came up past the doors of the church, but did not enter. The people could even take water to drink and it would be liquid, but it could not flow through the doorway.
Paul Does he provide any lesson from these?
Geoff Not that I recall, Paul, but it does seem that his readers could take comfort that although the world seems to be ending, as Gregory himself states at then end of book four, God has not left his people, and is still commanding reverence from unbelievers. In fact, in our current time, as Christianity has lost any currency in the market of ideas, and our Christian world is ending and we face “invasion” by ideas hostile to those of God, we can apply Gregory’s (and Elijah’s) lesson, that there are still holy miracle-workers in our time; there are still 8000 who have not served Baal.
Paul I’ve heard that Gregory also gives the life of St. Benedict?
Geoff Well, not exactly. Benedict’s stories encompass all of book two, but are mostly miracle stories in chronological order, so while you do see some of his life, it’s mostly miracle stories. They have a similar flavor to the first book, although maybe more reminiscent of Elijah.
Paul You make me eager to hear them, please continue.
Geoff So, in Benedict’s twenties, a group of monks asked him to be their abbot. He refused, saying that he was too strict for them. They persisted, and he agreed, but he was, in fact, too strict for them, and they poisoned his wine. But when Benedict blessed the wine with the sign of the cross, the cup shattered, and he realized that they tried to poison him. So he left that monastery, and went back to his wilderness. But later on he founded a bunch of monasteries, and encouraged many people. Some of the monasteries on the top of a mountain needed water, so he went there a night and prayed all night, put out three stones at the summit, and told them the next day to dig there, and there was already water under the stones. He also made an axe-head return onto the handle. A priest jealous of his reputation sent him a poisoned loaf of bread, but Benedict knew it was poisoned and had the raven he fed daily take it away where people wouldn’t find it (then the raven returned for it’s meal). When a young monk was killed and mangled by a falling wall, Benedict had them take the body into his room, and he prayed for a while, and the monk returned to life, restored to full health. Later in life Benedict started to “manifest the spirit of prophecy” (which, Gregory is clear about in an earlier discussion, is the spirit of Christ), so there are a number of stories of him foretelling the future, mostly about things like people delivering gifts to the monastery and keeping some for themselves (Benedict warned one such man to be careful of the snake in the basket he kept for himself, although the saint does not specifically call him out for his gift-theft). He also foretold Rome getting sacked.
Paul That is most impressive!
Geoff Gregory continues with more. He has many stories about righteous abbots and bishops being seen taken up to heaven, and then when the monks who saw it learn that the person has died, they find out that the person died exactly when they saw him being taken to heaven.
Paul How were they taken?
Geoff In many diverse ways. One person saw a long carpet stretched out before the person. Another’s spirit was seen as a dove, along with heavenly music, which got quieter as the dove flew higher and higher. One person saw the earth and heavens gathered together in a great light when a saintly bishop died.

Gregory also relates many stories about well-respected monks who had visitations regarding their deaths, although few of them understood this at the time. One monk had a saint visit him and tell him to prepare for a journey; he replied that he didn’t have any money to take the journey, to which the reply was that “you’re sins are forgiven, if that’s what you are referring to”. God told a different monk to prepare for a journey, too. Neither understood, but they died a few days after the experience. Visitors appeared to one sick monk while the others were gathered around him. They could not see the visitors, which surprised him, and he related a list of names that they said, including himself. Those monks died in the order that he had said. Another monk was given a letter by a visitor, perhaps it was an invitation, with names, including his own, written in gold. One nun who was told to come asked for a beloved sister to come with her, which—it was either God or some messenger, I don’t remember—was reluctant, but finally said, “in thirty days”. The nun died, and then the nun she asked for thirty days later.
Paul Those are very interesting stories. I presume he drew some lessons from them?
Geoff You are correct. Those are from the latter part of the book, especially book four which he explicitly says is to demonstrate the eternal existence of the soul (and therefore, that we should be concerned about to what eternity our actions are leading us). I assume that the saintly deaths, which often include a beautiful fragrance—one monk wept whenever he remembered the fragrance of such a one who died—and sometimes beautiful music. These stories are meant to illustrate that the soul is eternal.
Paul So was Gregory ending with a hellfire and brimstone message?
Geoff Sort of. It seems that the Puritans were hardly the first [e.g. “Sinners in the Hands of an Angry God” a famous sermon by Jonathan Edwards], nor Charles Finney. Gregory includes some stories about people went to hell. Usually these are inferred indirectly, such as one person buried in a church who was seen at night being dragged out. In the morning they found his grave in the church was empty and his body was outside the church, with the legs bound, as he had been seen. Another man was heard saying “I burn!” and his grave was empty except for his clothes. There were also some who came back to life, and some of these changed their ways, and some did not, illustrating that some love their sin too much.

He relates an interesting vision of where there is a bridge over a river to a meadow. In the meadow there is a house of gold bricks, and the bricks were brought by all the people who had received from the person. There was someone stuck face-down in the mud just short of the meadow, struggling with some sin. There was someone half-falling into the river and have on the bridge because of a serious sin. I thought the house—presumably our heavenly reward— being the return gifts from those to whom we have given to be quite a striking thought.

Gregory also tells stories about people who were saved, but had some serious sin. One nun who was diligently chaste but did not control her tongue, and the night afterwards she was seen, cut in half, with one half (maybe the bottom) burning. Several priests saw other people serving at the public baths, and inquired, and were told that they were serving because of their sins. One asked for prayer, another asked for Masses to be said for them; both said that when they did not see them again they would know that their efforts had been successful. Gregory uses these to illustrate that prayers and Masses on behalf of the dead are effective (as long as the sin can be forgiven, that is, the sin is not mortal).

Gregory basically ends the Dialogues by saying that the end of days is at hand (earlier, one of his stories was a monk who had a heavenly visitor who told him that, shortly before the Lombards invaded), and that we need to place an emphasis on being holy.
Paul Holiness seems to be very important to Gregory, then. Does he say how to be holy?
Geoff He sort of assumes that his readers know. But from the stories, it seems clear that the holy life is to give all your money to the poor, devote your life to poverty, chastity, and almsgiving. Basically, become a monk or a nun. He has one story about a man who was married, who it didn’t seem like became a monk, but he did stop having sex with his wife.
Paul That seems kind of hard for her.
Geoff Perhaps not, later in the story she shows him a lot of loving care. So perhaps she agreed to it.
Paul Do you think this view of holiness is feasible today?
Geoff There are still monks and nuns even today, and not only Catholics and Orthodox. But I do think that Gregory has a fundamentalist view of what holiness is, and I disagree with that. Gregory talks a lot about the importance of seeing the world as unimportant and focusing on heavenly things. But this seems to be a similar sort of gnostic impulse that, Anglican theologian N.T. Wright, for example accuses evangelicals of having. World evil, spirit good is a key component of gnosticism, but the Bible describes the world that God made as good. Jesus complained that while the Pharisees accused him of being a drunkard and glutton, but the Pharisees refused to accept John the Baptist’s world-renouncing self-denial either. One of the gospels portrays Jesus as the new Moses (as predicted by Moses), having come out of Egypt, and giving a new Law (e.g. the Sermon on the Mount). Well, Moses led the people from slavery, through the desert, into the Promised Land. Thus, Jesus, as the new Moses, has led us into the new Promised Land. So while we certainly cannot be attached to the world, to renounce it would be to renounce living in the Promised Land and insist on living in the desert. Which I’m sure God will honor, but wouldn’t it be better to practice living in the Promised Land? In this way we would be an example for the world of controlling our passions and demonstrating what living in the new Earth might look like.

I also think that monastic living does not work if everyone does it. If everyone embraces chastity, the entire Church would suffer the fate of the Shakers. They embraced a view of simple living and chastity, and all that remains is good furniture. (Actually there are a few people that adopt the Shaker way, so there are still a few Shakers.) The Church dying out in one generation does not seem like what Jesus had in mind. In a similar way, a lot of the saintly hermits depended on their friends to bring them food. So this clearly is not sustainable at scale. Monasteries provided for themselves, and emphasized freely giving, though, but there is still the chastity problem.

Your namesake, Paul, says that were are given all things to steward, and gives a long list which includes death. Jesus does say that it is hard for the wealthy to enter the Kingdom of Heaven, but on the other hand, if we are stewards of all things, then we should be stewards of riches as well. Which is not to say that we should seek to become rich. But on the other hand, avoiding having money also avoids learning how to be a steward of money. It seems to me that it is better to follow—is it Paul?—who says to receive all things with thanksgiving. Enjoy the good things of the world with thanksgiving, but hold them lightly because we are only stewards of them.

I also wish that Gregory had included stories about normal people who were holy. Perhaps in his view that is impossible. There are no examples of normal, married people who even had a holy death, let alone miracles. Maybe this is because monks’ and priests’ job was essentially serving the poor, so in some sense society had outsourced that role. But if Brother Lawrence (Practicing the Presence of God) could cultivate intimacy with God while cooking, surely normal people could cultivate intimacy with God while farming or performing their trade.
Paul You have given me a lot to think about. I find your explanations good, but you come to many opposite conclusions to Gregory.
Geoff I think Gregory is avoiding dealing with the tension between the one pole of self-denial and the other pole of thankful receiving and stewarding by chopping off the latter end. But Gregory’s stories are very engaging and encouraging, and they make me want to be the kind of person who has the kind of relationship with God that produces holiness of this quality, even if I think that Gregory has a unnecessarily narrow view of what holiness looks like. So even if you disagree, Dialogues is definitely worth reading. And if you do disagree, he makes you want to be develop or find a good metric for holiness.

Review: 10
I find this hard to review. It is a 1400-year book, far exceeding my 100-year standard. On the other hand, I think his view of holiness is at best excessively narrow and at worst, wrong. Yet, quality saint stories are always good to read (and certainly exciting), and they do encourage me to be a person with this quality. You can definitely see why, for instance, Alfred the Great translated Dialogues into (Old) English.