Slides can be accessed here

The Life and Legacy of St. Augustine: A Journey from Wayward Youth to Spiritual Giant

Today we reflect on the life of St. Augustine, one of the most influential figures in Christian history. Perhaps you’ve heard of his famous conversion story or meditated on some of his thought-provoking quotes. Over the past few weeks, I’ve had the blessing of reading about his life, and I hope his story can instruct and inspire us as well.


Legacy

Before we dive into his personal story, let’s consider Augustine’s legacy. He was a prolific writer, leaving behind:

  • Over 300 sermons
  • 500 letters
  • An extensive body of writings, including five of his most influential works: Confessions, The Enchiridion, On Christian Doctrine, On the Trinity, and The City of God

Confessions is a spiritual autobiography written in the form of a prayer to God. Augustine has been called the most influential theologian in church history, second only to Jesus and Paul.

His influence spans theology and philosophy. Churches, monasteries, cities, monuments, and schools bear his name. He shaped both Catholic and Protestant thought:

  • Catholic: impact on ecclesiology
  • Protestant: influence on soteriology and historic Reformed theology

Luther was an Augustinian monk, and Calvin cited Augustine 342 times in the 1559 edition of Institutes of the Christian Religion.

Even the motto of Desiring God Ministries “God is most glorified in us when we are most satisfied in Him” reflects Augustine’s influence, emphasizing the enjoyment of God as the ultimate fulfillment of human desire, the so-called “Augustinian Roots of Christian Hedonism.”

So this spiritual giant clearly left an impact on Christianity, and one would imagine that he was a sanctified saint from the womb, trained in the Scriptures, living a holy life from his youth. But that’s not the case. He initially lived a very secular life, plagued by youthful passions, flirting with women and liberal ideologies.


Before Christ: A Wayward Youth

Augustine was born November 15, 354 AD, in Thagaste (present-day Algeria), North Africa. He was the eldest child of:

  • Monica: a devout Christian whose persistent prayers profoundly influenced him. Santa Monica, California is named in her honor. She became venerated as a saint for her enduring faith and prayers for her son.
  • Patricius: an unbelieving lower-middle class Roman official whose desire for his son was that he get the best education possible. He would work hard to pay for Augustine’s tuition so that he got the best Roman education in rhetoric. Augustine doesn’t write much about his father, only to express disappointment in his father’s care for him. He didn’t seem to care if Augustine lived a chaste life or not, but simply that he knew how to make a good speech and persuade others with words.”

He had at least one sister, Perpetua, and one brother, Navigius, though little is known about them.

From an early age, Augustine excelled in rhetoric, the most admired and lucrative career in the Roman Empire. By age 19, he became a teacher of rhetoric.

He was part of a close-knit group of friends, mischievous and indulgent, who amplified sinful desires. A famous story, the Pear Tree Incident, illustrates Augustine’s understanding of sin as a perversion of the will—the pleasure is in the act itself, often influenced by peer pressure.

At 16, Augustine went to university in Carthage, where he pursued both sexual pleasures and philosophical ideologies:

  • He fathered a son, Adeodatus, with an unnamed concubine, living with her for 15 years
  • He explored Manichaeism, drawn to its secretive, ascetic, dualistic philosophy
  • Augustine was curious but dismissive of the Scriptures. He flirted with philosophical thought and at 25 years old became affiliated with the Manichaeans, which was named after an Iranian prophet named Mani. It was a mix of Zoroastrianism, Buddhism, Christianity, Gnosticism and a big competitor to Christianity in the 3rd and 4th century. It was dualistic: light side and dark side, good and evil and the followers were disciplined, ascetic, seeking wisdom. He was appealed by the “secret” and “hidden” knowledge. But after Augustine’s close friend died, he questioned his Mani teachers but they couldn’t answer his questions with any satisfaction. Augustine saved up his questions and asked Faustus, the leading Manichaen of his day. Augustine became unimpressed and disillusioned when he learned that Faustus wasn’t as intelligent, educated as he thought he would be. That’s when he started walking away from Manichaeism.

Monica: The Power of Prayer

Augustine’s mother, Monica, was relentless in prayer. For three decades, she prayed for her son’s salvation and sought the guidance of church leaders to influence him. Her witness and persistence highlight the role of parental and spiritual influence in shaping saints.


Ambrose: Mentorship and Guidance

Augustine eventually became a public orator in Milan, where he met Ambrose, the bishop of the city. Ambrose’s intellectual depth, wisdom, and serenity captivated Augustine. He became a mentor and an intellectual sparring partner, helping Augustine engage with Scripture more seriously.


Conversion: The Garden in Milan

Around 386 AD, at age 31, Augustine experienced his dramatic conversion. In a garden in Milan, tearing at his hair and crying, he heard a child’s voice chanting in Latin: “Tolle lege, tolle lege” (“Take up and read”).

Augustine obeyed and plays Bible Roulette and it lands on Romans 13:11-14. That moment marked a turning point, leading him into a life fully devoted to Christ.


After Christ: A Life of Influence

Following his conversion:

  • He turned his house into a godly fraternity
  • Became Bishop of Hippo
  • Faced the siege of the Vandals
  • Engaged in theological battles against Pelagianism (the belief humans can choose good independently of God) and Donatism (questions of church purity and sacramental validity). Pelagianism named after his contemporary and arch-antagonist, British monk Pelagius (lived in Rome).

Wisdom and Reflections

Some of Augustine’s enduring quotes:

  • “Pray as though everything depended on God. Work as though everything depended on you.”
  • “Love God and do as you please. For the soul trained to love God will do nothing to offend the one who is beloved.”
  • “He cannot have God for his Father who will not have the Church for his mother.”
  • “Our hearts are restless until they have found their rest in You.”

Augustine’s journey reminds us that spiritual giants are often shaped by struggle, doubt, and persistent pursuit of truth. His life challenges us to reflect on our own spiritual path, the influence of mentors and loved ones, and the transformative power of God’s grace.