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In the year 383 Augustine sought his fortune in Rome, the centre and capital of the Empire. He had become uneasy in Carthage once his ambitions had outgrown North Africa. He already knew some people in Rome. These included his good friend, Alypius, and a number of his former pupils from Carthage. Several of them had written to invite him to Rome. They created attractive possibilities in the imagination of Augustine. They told him that the students in Rome were better than those in Carthage, and that he would earn more money. Possibly because this was what Augustine wanted to hear, he believed them.

And he was further encouraged by Manichean contacts in Rome to help him to become established.  It also was an opportunity for him to escape the presence of his mother, Monica. Her desire for his baptism was something about which mother and son disagreed. She clearly told him about what her Christian viewpoint saw to be his heretical adherence to Manicheanism. [See Confessions 5, 8 & 9] In spite of the appeals from his mother, Monica, he lied to her about his travel plans and sailed away at night from the African continent to Europe. This was to be both his first and his only voyage to Italy. Rome of the fourth century was no longer a city with political or military significance for the Roman Empire, but nobody at the time dared to say it. By common consent, the pretence was maintained that the city of Rome was the hub of civilisation, and so the pretence became a hope that fulfilled itself.

Prestige is a matter of reputation rather than of reality, and Rome had a reputation that stretched back for centuries. Augustine took a few months to find a place there. On top of that, he did not reach Rome at a good time. The city was suffering famine subsequent to the revolt by Maximus in June of that year. As well, Augustine promptly contracted a fever that almost killed him. He had to be supported by friends until he recovered, and his dependence on them was a blow to his pride.

As soon as Augustine regained his health, he began to recruit students. To obtain them, however, was far easier than having them pay their fees. In fact, he had been better financially back in Carthage. As well as this financial problem, he was affected by the Roman climate. He could not endure its humid air, or the uneven surface of its streets. The coarseness of Roman manners also disappointed him; although not innocent of vice himself, he nevertheless had expected a higher culture in the capital city of the empire. There were the crudities, in the theatres and elsewhere, spoken against all foreign immigrants. Worst of all, he saw a lack of interest in intellectual matters, even among those who claimed to be most cultured. And he was disturbed by the behaviour of the upper classes, and by the many temples dedicated to all kinds of gods. He disliked the lack of respect for human life, and most of all for the life of a slave or a captured foe. All these things began to depress him. All in all, during his first year in Rome, Augustine was neither satisfied nor successful. He was alone now more than ever previously, and reflected on his situation.

Possibly he sensed that a turning point was coming. Did he suspect that he was a slave to his pride, no matter how much he might be denying it? In this milieu, Manicheism was not providing him with any encouragement, and hence had almost lost its hold over him. As once he had used his intelligence to defend it, so now it amused him to tear Manicheism to pieces. Because he as yet had nothing with which to replace Manicheism, he nominally clung to it still.This at least provided him with a convenient cloak with which to excuse the parts of his behaviour which as yet he still felt unable to change.

Through sheer poverty, Augustine apparently believed he would have to return to Africa. This would have entailed a loss of pride for him, and would mean uncomfortably facing his mother there. And then he heard of another possibility. A valued teaching position in rhetoric at Milan was being advertised. Through Manichean influence Augustine succeeded in obtaining it. Milan was the city of the Roman Emperor and his court but, more importantly in the unfolding of the life of Augustine, it was also the city of Ambrose, the leader of the church in Milan.

Symmachus, pagan patron of Augustine in Rome

Quintus Aurelius Symmachus was in Rome the pagan patron of Augustine, who granted Augustine the teaching position in Milan.The way in which Augustine obtained that position is often told in a casual manner that allows the false impression that Augustine obtained the position solely because of the influence of the Manichees, of which sect he was still at least nominally a member. Influence certainly opened the doors so that Augustine could apply for the position but, once he was interviewed and examined, he was granted the position because he was the best candidate seeking it.

Quintus Aurelius Symmachus (c. 340-402 AD) was the Prefect of Rome. He was everything that the ambitious young Augustine admired - wealthy, eloquent, and respected as a born leader. He was also a dedicated pagan at a time when paganism was on the wane, and the influence of the Christian religion on society was inexoerably increasing. It concerned Quintus Aurelius Symmachus that in the Roman Empire was being tolerated rather than supported. As a conservative aristocrat, he fought this trend. But he was unequal to the challenge that he received in this regard from his powerful cousin: Ambrose, bishop of Milan.

In the life of Augustine, it is ironic that it would be Quintus Aurelius Symmachus (a pagan) who would send Augustine (then an agnostic) to Milan, where Ambrose (the cousin of Symmachus) would precipitate the conversion of Augustine to the Christian Faith. Ambrose was influential with Gratian (Roman emperor, 367–383 AD), who tended to favour Christian ideals. Ambrose convinced Gratian to remove the Altar of Victory from the Roman senate chamber —an obvious blow against Rome's pagan tradition.

The Senate of Rome sent Symmachus to Milan to plead with the emperor to replace the altar. Though eloquent, Symmachus failed in his mission. The influence of Symmachus was sufficient, however, to give the career of Augustine some practical help. In 384 a government position for a teacher of rhetoric in Milan was vacant. Some the Manichee friends of Augustine recommended him to Symmachus for the position. Augustine later said, "Symmachus … set me a test to satisfy himself of my abilities," after which the young Augustine won the post easily.

Augustine won the position of teacher of rhetoric in Milan, because of his abilities and because Symmachus was pleased to have the position go to a person who was not a Christian. Later in his Confessions, Augustine saw that it was God’s plan that he went to Milan. He wrote, "To Milan I came, to Ambrose... To him was I led by You, Lord, that by him I might knowingly be led to You. That man of God received me as a father... I hung on his words attentively."

He also stated, "Ambrose had a message to communicate, and was not additionally trying to entertain by using polished phrases….. Ambrose was one who spoke the truth, and preached it well, judiciously, and with beauty and power of expression." In a similar line of reasoning, Divine Providence also placed Symmachus in a position unknowingly to assist Augustine to transfer to Milan. 

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