In ancient times the city of Damascus employed a system of subterranean canals that irrigated the plains and supplied Damascenes with drinking water. Some of these aqueducts were more than a mile in length. It was through these canals that Saint Paul escaped the city to enter Arabia (Gal 1:17), and through them he returned to Damascus following his time in the wilderness (Acts 9:19b-20).
In those days Damascus was ruled by a governor under the Arabian king Aretas IV (4BC-AD 40). Aretas was the Nabataean king whose daughter was married to and divorced from Herod Antipas. Aretas ruled Damascus at the time of the conversion of Paul, and the Arabian governor tried to arrest the Apostle at the behest of the Jews (2 Cor 11:32). It was this governor, or ‘ethnarch’ of Aretas, from whom Paul escaped from Damascus and then returned to Jerusalem. “At Damascus, the governor of Aretas guarded the city in order to seize me, but I was lowered in a basket through a window in the wall and escaped his hands.” In Syria at this time conflict arose between Aretas and Antipas because of the divorce. Herod divorced Phasaelis in AD 29 to marry Herodias, and Aretas vowed revenge. Conflict mounted, and war broke out between the Arabian sheik and the Galilean ruler in the mid-to-late 30s.
The hubris of Aretas to declare war against a brother feudatory and to occupy a city previously under Roman rule angered Tiberius Caesar. Vitellius, the Syrian governor (a peer of Pontius Pilate) ordered attacks against Aretas.  Politically astute, Aretas possessed the political savvy to obtain allegiance from the Damascene Jews (no supporters of Antipas) rather than risk defeat, for the Roans backed Antipas. Diplomacy could have worked but Aretas refused to negotiate lest he lose Damascus.
In his Letter to the Galatians Paul writes that he spent three years in Arabia and Damascus after his conversion, AD 36-39, which coincided with the war between Aretas and Antipas and Rome. In Arabia, Paul he attempted to evangelize Aretas and his court, and to convince the king to make peace with his enemies. He avoided Jerusalem and Judea, for he knew the Jewish officials waited to capture him. Instead he returned to Damascus, the city he left several weeks earlier, moving along the fringes of the desert, the land east of the Jordan River. This was the territory where John the Baptist preached (Mt 3:1) and where Jesus spent 40 days and 40 nights in the desert to prepare for his three-year ministry (Mt 4:1-11; Mk 1:12-13; Lk 4:1-13). On the way to the city, Paul passed by the site where he received the Revelation (Acts 9:4-6). Now in full possession of his senses, he returned to Damascus a new man, born again, raised from the dead, in Christ. On his journey through the wilderness, he scaled mount Sinai where he conversed with the prophet Elijah, sought an audience with Aretas in Petra and attempted to evangelize the king and his subjects, and stood on the shore of the Red Sea, the site where the Lord God destroyed Pharaoh’s army and liberated the Israelites. Now Paul possessed greater knowledge of Salvation History. A suffering Messiah was not something that Paul could have accepted the day he left Jerusalem for Damascus to arrest Jesus’s disciples. The revelation led him on a spiritual journey and prepared him to accept his commission to be the Ambassador for Christ. His journey as the Apostle began.
Eight gates led into various districts in Damascus. Paul entered the gate at the eastern wall, and walked discreetly through the narrow streets toward the Jewish quarter. He did not seek the house of Judas; rather, he went to Ananias, the servant of God who baptized him. (Acts 9:18b). Paul respected Ananias, as a “devout man” with a good reputation even among synagogue leaders. (Acts 22:12). Soon Paul learned of the deal struck between the Jews and the civil authorities to assassinate him. His enemies appealed to the governor of Aretas to arrest Paul on charges of sedition and blasphemy. The disciples harbored Paul and he managed to gain disciples of his own. “He stayed some days with the disciples in Damascus” (Acts 9:19b) and accepted the hospitality of the men and women whom he had come to Damascus to destroy. Everything was different now; he was one of their own.
Now the greatest decision of his life lay before him. Ananias told him that he was to be a witness to the world of the Revelation of Jesus Christ. The Lord declared to Paul that he was a “chosen instrument of suffering, to carry my name before gentiles, kings, and Israelites” (Acts 9:15). His thoughts gripped him. What should he do? Obey the vision or resume his status as persecutor? He had committed no irrevocable offense, had not broken with his nation. He did nothing that the high priest would not pardon. True, he did not carry out the mission to destroy the Church, an assignment he requested. And he sympathized with the Christians. He was one of one them, grafted into the Body of Christ through baptism forever. The revelations in Arabia, were they real? He struggled in his heart to understand, knelt before the crucifix and prayed. “Lord, you know the hearts of everyone. The words of Moses are true. ‘I set before you life and death, a blessing and a curse. Choose life then, by loving the Lord, your God, heeding his voice, and holding fast to him, for that will mean a long life for you’ (Dt 30:19b-20).” The solution to his struggle formed the crux of the first 30 years of Paul’s life and set the course he followed the remainder of his days. Saint Luke illuminates the truth in Paul’s heart: “Straightaway he went into the synagogue and preached Christ crucified and risen” (Acts 9:20). This was what Paul was born to do.
There were as many as 40 synagogues in Damascus. In the 30s of the first century about 40,000 Jews lived in the city.  It was not difficult for Paul to obtain access to worship spaces given his reputation as a learned Jew, the student of Gamaliel. Synagogues held services thrice weekly, when members prayed, praised God, sang hymns, and instructed children. The Old Testament indicates that synagogues developed during the Babylonian captivity 500 years before the birth of Christ. Jewish exiles, torn from the holy city, detained for 70 years, established worship sites as an alternative to the temple, the throne of the Great King’s city, thrown into ruin by gentiles. The exiles returned and synagogues developed rapidly and became a staple in Jewish religious tradition, due to the work of the scribes Ezra and Nehemiah (5th century BC). The synagogue provided a sacred space for the reading of the Torah, for canting hymns, and for prayer, and as a setting for debate on the identify of the Messiah. In the gospels Jesus frequented the synagogue where he preached the kingdom (CCC 442, 1388, 2586, 2599, 2701). Paul himself regularly attended the Synagogue of the Freedmen in Jerusalem where he first encountered Jesus through the preaching of Stephen.
Ancient synagogues assumed a single form: a rectangular building with its entrance at the front. Inscribed over the entrance were the words of Moses: “Take these words of mine into your heart and your soul. … Teach them to your children. … Write them on the doorposts of your houses and on your gates” (Dt 11:18a, 19b, 20). At the opposite end of the worship space stood the assembly’s most precious treasure: the ark containing the scrolls of the Law, the Prophets, and the Writings. Between the ark and the assembly hung a veil to screen the Word from the congregation until the service began (2 Cor 3:13). The rulers and the elders sat adjacent to the ark; before them opened the worship space where a wall segregated the men from the women. At the center of the synagogue stood the high pulpit from which the writings were proclaimed and where the exegete preached a sermon.
As a missionary, the synagogue was Paul’s integral access into the communities he evangelized. He always began his missions in the synagogue, to preach to the lost sheep of the house of Israel (Mt 10:6). The archisynagogus (synagogue leader) called on him to read at the Synagogue of the Freedman in Jerusalem (Acts 6:9) and, like Jesus and Stephen, Paul taught in the synagogues where he gave “ a word of exhortation to the people” (Acts 13:15). As a Jew he still retained his right to preach. All synagogues in Damascus were open to him. He was the pupil of Gamaliel, the apostle to the high priest, and his sudden blindness was cured at the hands of Ananias. Few could deny the miracle. He could not remain anonymous; he proved to be an attractive addition to each house of prayer and study that he graced. “The eyes of all in the synagogue looked intently at him” (Lk 4:20). The congregants wanted to know Paul’s thoughts on the Writings, the Prophets, and the Law, the scriptures that led the faithful to Christ. He ascended the pulpit and received the scroll from the attendant and commenced to ‘preach Jesus’ (Acts 17:18) and all who heard him balked and were astonished, the claim he delivered, revolutionary: the salvation of Israel, indeed the entire world, rested on the crucified Nazorean. Paul exhorted his hearers to look to Christ, to Christ alone, for the forgiveness of sins, and he warned them against rejecting the Savior as did the Jews at Jerusalem (Acts 13:23-41).
All who heard him were amazed, and said, “Is not this the one who destroyed those that called upon this name in Jerusalem, and came here to bind them in changes and bring them back to Jerusalem to the chief priests?” (Acts 9:21). And their was division among them.
Scripture tells us that Paul remained in Damascus for another year and “preached boldly in the name of the Lord” (Acts 9:27). But the synagogue leaders refused to let him preach to their assemblies. Everything he said contradicted their ideas on the Messiah. When he could no longer lift up his voice at the pulpit he took recourse to lecture in the adjacent halls of study. In such schools Stephen debated the Jews from Alexandria and Cilicia (Acts 7:9), with Paul among his opponents. Now Paul taught the “faith that he tried to destroy.” At first the rabbis did not deny the famed disciple of Gamaliel to proclaim his ideas, for such was the argumentative force with which he taught that opponents were riveted and his renown spread through the city. Opposition arose.  The belief in a suffering Messiah was no more acceptable in Damascus than it was in Jerusalem when Christ proclaimed his truth. The Jews met and instructed the rabbis to oppose the theology of the young preacher. Profound in his knowledge of Scripture, Paul confounded the rabbis (Acts 9:22), giving them no recourse but to shut him out. In rage and humiliation they devised a plot to kill Paul (Acts 9:24). When the disciples learned of it they urged Paul to leave the city. “When they persecute you in one city, shake the dust from your feet, and flee to another city” (Mt 10:23).
Paul sought the protection of civil authorities. It was his practice to insist upon his civil rights, as a Jew and as a Roman. “Do you indeed sit in judgment of me according to the law and yet in violation of the law order me to be struck?” (Acts 23:3). He appealed to the leader of the Jewish quarter for protection, bound by the law as he was to defend Jews in his jurisdiction. As a Roman Paul had recourse to appeal to Roman courts for similar protection. At least, that was how it appeared on paper. Circumstances in Damascus proved to be such that the rights Paul expected became untenable. Petition to Jewish authority was unwise; sharing the prejudices of the religious leaders the police and the lawyers desired the death of the ‘heretic’ as well. “Away with such a fellow from the earth!” (Acts 22:22). Paul held no hope that his compatriots would afford him protection under the law. His standing as a Roman citizen offered him no more benefit than his status as a son of Israel. Paul was a victim of circumstance, for at that time the Syrian city passed from the direct reign of Rome into the hands of the Arab sheik Aretas IV, sitting on his throne at Petra.  The takeover compromised the authority of the Roman prefect and Aretas was recognized as the supreme ruler of the city, though his feudatory power derived from Tiberius Caesar. Like Antipas in Galilee, Aretas was a client king of Syria under the auspices of Rome. Yet he bucked Rome’s authority and at an opportune moment seized control of the Syrian capital. The dominion of Aretas was absolute. Paul had no recourse to the Roman courts and the governor of Aretas was in league with Jewish authorities; together they colluded against the Apostle (see 2 Cor 11:32; Acts 9:23-24).
Only God’s grace through baptism could help Paul escape the powers of darkness (Acts 26:17-18). The Jewish authorities were of no use. The Damascene ethnarch was in league with the Jews and willing to help them assassinate Paul. His only option was to go underground. The Christians harbored him in their houses placing the Church at risk but under the circumstances they could not refuse; baptized into the faith, he was their brother. Soon the Apostle felt confined and inactivity compelled him to action. His heart ached to “preach the gospel to every creature” (Mk 16:15), and the conviction that he was neglecting his commission motivated him to find new vineyards in which to labor despite the risk. “If I preach the gospel, this is no reason for me to boast, for an obligation has been imposed on me, and woe to me if I do not preach it!” (1 Cor 9:16).
Paul’s disciples devised a plan to help him escape the city. The difficulty was palpable: Damascus was a walled city; it was easy for his enemies to watch the gates “day and night” (Acts 9:24). The governor of Aretas was in league with the Jews and his soldiers interrogated all who came and went through the gates. Unless Paul could contrive a disguise, he would certainly be discovered when he attempted to leave the city. It occurred to the disciples that a man could escape the city without passing through the gates. In the Book of Joshua Rahab the harlot helped the Israelite spies escape by lowering them by a cord through the window of her house, which abutted the city walls of Jericho (2:15-22). King David did not consider such a means of escape to be beneath him either: “Michal let David down through a window and he made his escape to safety” (1 Sm 19:12). A similar plan could work for Paul. Private houses adjoined and overhung the walls, with windows overlooking the open country, through which a man might be let down over the wall. So one night, while the soldiers of Aretas and the Jews watched the city gates, Paul snuck into the house of a Christian built into the city wall. A large basket fashioned by rope with a strong cord was procured. The Apostle, after bidding his brethren farewell, stepped into the basket and, grasping the cord, was lowered slowly and deliberately from the window. It could be said that of such an escape came humiliation, but Paul believed that the disciple of a crucified Redeemer should be prepared to encounter shame, and he “rejoiced that he was counted as worthy to suffer for the sake of the name” (Acts 5:41).
Paul tumbled from the basket onto the ground and stood on his feet. “Get up now, Paul” Jesus said, “and stand on your feet.” The Apostle took one long look at the city, the site where he met Jesus. Then he started south, the darkened peaks of snowy Hermon to the west. Finally, after three years, he was going up to Jerusalem to confer with Peter, James, and John (Gal 1:18). Wouldn’t they be surprised?