During the birth of humanism, Dionigi di Borgo San Sepolcro O.S.A. (c. 1300 – 31st March 1342) was the priest who at one time taught Boccaccio at the beginning of his education in the humanities, and was the confessor of Petrarch. He later was Bishop of Monopoli in Apulia, Italy.

He was surnamed, not uncommonly for the 14th century, for the town in which he was born, now called Sansepolcro - a small town in the mountainous regions of Tuscany. His family surname was de' Roberti. (Dionigi is the Italian form of Dennis, which in Latin is Dionysius.) He joined the Augustinian Order at Borgo San Sepolcro at an early age; this convent had been founded in 1281. He was sent to the Augustinian studium generale (international study house) in Paris in order to study theology, and graduated as a bachelor in 1317-1318, and a doctor of theology in 1324.

This was still an era when education was as yet totally based in the Scholastic tradition. The universities did not yet place Greco-Latin philosophy consciously at the service of Christian thought. Instead, in these birth years of humanism, they sought simply to increase the authority of the ancient writers. Thereby they were paving the way for future humanistic orientation. Likewise they sought to know classical literature through the original text, eschewing secondary sources or florilegia.

After he left the University of Paris, Dionigi travelled widely. In 1329 he went on an unspecified diplomatic mission for Cardinal Napoleone Orsini, in 1332 he was in Venice, in 1333 he spent much time in Avignon and taught at the studium (Augustinian house of study) that the Augustinian Order conducted there. He was held in great esteem within the Augustinian Order, both at the Papal curia in Avignon, and later at the court in Naples.

Dionigi certainly met Francesco Petrarch (1304 – 1374) in Avignon, and there is another theory that these two scholars had already met previously in Paris. He was Petrarch's confessor in Avignon, and Petrarch wrote three letters to him. Much of what is known about Dionigi in his Avignon years is inferred from these letters. It was Dionigi who introduced Petrarch to the works of Christian antiquity, and in particular to those of St Augustine. The desire of Petrarch to achieve a synthesis between classical antiquity and Christianity, taking as his guide the bishop of Hippo, was due largely to his Augustinian mentor.

Dionigi had recommended Augustine's Confessions to Petrarch, who had never previously read it; Dionigi gave him a pocket copy, which Petrarch says he carried around with him everywhere. Much later in life in life Petrarch acceded happily to a request of Luigi Marsigli O.S.A. (1342 – 1394, i.e.,  thirty-eight years Petrarch’s junior) for a copy of the Confessions of St Augustine. Petrarch told Marsigli that the book being sent was not a loan as requested, but a gift. He added that in his youth he himself had received that very same pocket-sized book from Dionysius of Borgo San Sepolcro. He noted, "It shows the wear of years since it has always accompanied me on my journeys, but it gives me great satisfaction to see that this book, which originally came from an Augustinian house, now returns to another Augustinian house."

It had been suggested that Dionigi's influence on Petrarch in his moral crisis over Laura amounted to some form of spiritual conversion experience for Petrarch, but the more fundamental question of how much Laura’s portrayal in Petrarch’s writing was “real” and how much it was literary licence – or even total fiction - makes this suggestion even more tenuous. In his Secretum, Petrarch addressed his long account of his ascent of Mont Ventoux to Dionigi. Dionigi was also instrumental in persuading King Robert of Naples to present Petrarch with his crown of laurel: Petrarch had invited Dionigi to visit Vaucluse on his way to Naples in 1338, in a verse letter filled with flattery of the King.

Petrarch later included in his own listing of his "favourite books" Augustine's Confessiones (“Confessions”), De civitate dei (“City of God ”), Soliloquium (“Soliloquies”), and De vera religione (“About True Religion”). In 1335 Dionigi was in Grasse. In 1337 he went to Florence. In 1338 he accepted the invitation of King Robert of Anjou to teach in the king's academy in Naples. He then remained in the Kingdom of Naples for the rest of his life, and lived in its Augustinian convento. In this environment Dionysius found a favourable climate for his own spiritual preferences.

The brilliant circle of learned men that the king of Naples had gathered not only men of a rigid Scholastic formation but also a good number of advocates of the first tendencies toward humanism. Dionigi was able to teach in the university according to his own academic interests. In that capacity he became acquainted with the young Giovanni Boccaccio (1313 – 1375), who was a law student at the same centre and, becoming acquainted with Dionysius, took him as a paternal friend. Boccaccio been welcome in the court of King Robert of Naples since 1327, when the former was a precocious youth only fourteen years of age.

It was Dionigi who awakened in Boccaccio his first enthusiasm for the writings of a second pillar in the birth of humanism, Francesco Petrarch. The friendship of Petrarch with friar Dionigi was foundational for the former, who later became called “the prince of humanism.”  The young Petrarch was the recipient in this relationship, for Dionigi was already a learned professor, well acquainted with classical literature. When Dionigi arrived in Naples, he persuaded King Robert to write Petrarch, and Petrarch responded to both of them, congratulating Dionigi on having the favour of so famous a king, and reminding him enthusiastically and thankfully in a postscript: "You know what I think about the laurel." Dionigi also arranged Petrarch's visit to Naples in February 1341, when King Robert examined him for his fitness for the laurel.

Dionigi had introduced Boccaccio to the works of Augustine, Seneca, and Petrarch; possibly he had also taught him vernacular poetry and rhymed prose. Besides his teaching activity in the service of the Augustinian Order in particular and of the church generally, Dionigi displayed noteworthy skill as a writer. Along with theological tracts, he composed commentaries on various works of secular authors: the Politics and Rhetoric of Aristotle, the poems of Virgil, the Metamorphoses of Ovid, and the tragedies of Seneca. No doubt these commentaries grew out of the lectures he gave to his students, and were the fruit of his extraordinary knowledge of classical literature. In so doing he was the first university professor to advance the study of the classical authors at the dawning of humanism. None of these commentaries is any longer extant, but they must have been circulated among his disciples and admirers.

Much more is known about his commentary on the nine books of the Facta et dicta memorabilia of Valerius Maximus. In this work Dionysius chose from the text "examples” to which he sought to give a more profound moral and philosophical content, and to explicate them by drawing upon citations from classical and post-classical literature. The impressive list of Greco-Latin authors, fathers of the church, and medieval writers that he used in the composition of the work naturally awakened suspicions that his knowledge of these texts was not always direct. However, an analysis of the texts cited indicates that a great part of them were known from the primary sources and that he sought to compare the citations with the original text. His attempts to offer his reader as accurate a reading as possible were noteworthy.

He was not even content to base his judgment on a single manuscript but consulted a variety and noted in his exposition a good number of variant readings. To be sure, his method of textual criticism was still rudimentary, but in the light of the times, it was a worthy attempt to resolve the problems of textual criticism. This commentary gained for Dionigi the title expositor of Valerius Maximus and assured him an honoured place in the history of the early stages of humanism. In the first hundred years after his death, his work was used as a source and model for many other commentators of the same author.

Only in the second half of the fifteenth century, when Greek began to be known in the West and thus made available in new texts of Valerius, did the influence of this Augustinian humanist begin to wane. Proof of the value of his work can be seen in the many codices which are still preserved, as well as the wide dissemination the printing press gave it after 1475.

Most of Dionigi's writings are lost; but still extant are:

• A commentary on the first book of Peter Lombard's Sententiae (on which, as was common, he had given his baccalaureate lecture)

• a treatise on logic,

• a commentary on Aristotle's Economics

• a commentary on Valerius Maximus

The last of these was printed in Strasbourg in the 1470s. Some other commentaries have been attributed to him.

Dionigi won the favour of King Robert of Naples for his astrology and his classical Latin; as early as the winter of 1338, King Robert appointed him to settle a quarrel among the factions of the citizenry of l'Aquila. A document of dispensation for a marriage he performed survives among the correspondence of Pope Benedict XII. On 17th March 1340 he was consecrated Bishop of Monopoli at Monopoli in Apulia, Italy, at the King's request. He died on 31st March 1342; Petrarch wrote the final words of his epitaph: Flere libet, sed flere vetor. Giovanni Boccaccio, who had lived in Naples, returned to Florence, probably at the end of 1340. He subsequently wrote a letter there, bemoaning the death of his "reverend father and teacher" Dionigi, whose death he said left nothing for him in the world. 

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