What does Luke 5:27 mean?

Jesus' choice of fishermen for His first four disciples was unique (Luke 5:1–11). They were uneducated and, if Peter's reaction is any indication, did not enjoy especially holy lifestyles (Luke 5:8). Jesus is more interested in humility and the willingness to repent than holiness; if they come, He'll provide all the righteousness they need.

Even so, to choose a tax collector is a bold move. Tax collectors were typically Jews—or at least locals—employed by the Romans to collect funds from the people. Basically, they took money from their countrymen to cover the expenses of the foreigners who occupied their territory and ruled over them. Not only did the Romans pay tax collectors well, the Romans did not care if the collectors took more than the tax required. They were free to take as much as they could for themselves—once the Romans had been paid.

The Greek terminology indicates Levi is a low-level tax collector. He's not a chief like Zacchaeus (Luke 19:2); he likely collects tolls along the road along the western shore of the Sea of Galilee. Yet he would still have been seen as a state-sponsored thief who socialized with the fringe of respectable society. When Jesus walks along the Sea (Mark 2:13–14), He sees Levi. That is, Jesus intentionally focuses on this man. He doesn't pass Levi by out of disgust or ignore him out of pride. Then, Jesus calls him to be publicly identified with Him. This is great for Levi, now the disciple of a rabbi who is well-respected by the people. But it can only hurt Jesus' reputation with the religious leaders (Luke 5:30).

This is the second of three times Luke describes Jesus' calls of His twelve closest disciples (Luke 5:1–11; 6:12–16). When the group is settled, Jesus will call crowds to a more general followership (Luke 6:46–49; 8:4–21) and then challenge the Twelve to a deeper commitment (Luke 9:18–50).

Some versions, including the King James, uses "publican" instead of tax-collector. "Publican" is a translation of the Greek word for "tax-farmer."

Levi—Matthew—has been the subject of much speculation. Fictionalized accounts of the New Testament have suggested he may have been on the autism spectrum. This is not impossible, but there is no indication that the historical Levi actually was in such a category.