[The] gospels do not speak at length or even frequently about Jesus “hanging out” (as people say) with prostitutes or even with sinners. When we account for the repetition of the same narratives in the synoptic gospels (i.e., Matthew, Mark and Luke), we can focus on three passages: Matthew 9:10, 32-32; and Luke 15:1 and gain a clearer picture.
Matthew 9:10: Jesus at table with sinners
And it was when Jesus reclined in the house and behold there were many tax collectors and sinners coming and reclining with Jesus and his disciples.
The reclining here refers to the practice of way people ate dinner in first-century Judea. Where Western cultures tend to sit at (the) table to eat, they reclined. There can be no doubt that Matthew (and Mark and Luke) want us to understand that Jesus and his disciples spent time with those who were regarded by some, e.g., the Pharisees, as morally impure and thus corrupting of society disqualified from social intercourse.
That our Lord is shown spending time with sinners and other ritually and socially unclean people is part of a broader pattern in Matthew and the other synoptics. In Matthew 8:1–4 he cleanses a leper. They were ritually unclean and of course a potential threat to public health. Under Levitical law, he was to be excluded from the community and marked as unclean and to be isolated as long as he was infected (Lev 13:42–59).
Then we see our Lord healing the servant of a hated Roman centurion. Here is a class of interaction with the unclean that is usually neglected. In a Marxist or class-oriented rendering of Christianity, where the world is reduced to oppressors and the oppressed, we should be surprised to see Jesus not only interacting with the oppressor but graciously healing his servant (Matt 8:5–13).
In Matthew 28:–34 we see our Lord healing two demon-possessed men among the Gaderenes and in proximity to pigs, which were regarded as unclean (Deut 14:8). In this account Jesus not only offends the Pharisaic “fence around the law”, i.e., their regulations designed to keep Jews from transgressing the 613 commandments (as the rabbis counted them) but he also managed to offend contemporary animal-rights activists. After all, what had those pigs done to anyone that Jesus should send the demons into them and thence over the cliff.
Matthew’s narrative of potential offences continues in Matthew 9:1–8 where he heals a paralytic, which, obviously, is not offensive in itself but he also presumed to forgive his sins (v. 2), which the Scribes regarded as blasphemy. He transgressed the Jewish social code when he called as one of his disciples, Matthew, a tax collector (Matt 9:9). Those Jews who collected taxes for the Romans were hated by the Jews for their collaboration with the hated Roman oppressors. It is in that context that Matthew reports that Jesus reclined at table with “many tax collectors and sinners.” Predictably, the Pharisees were outraged at this (v. 11).
Jesus’ defence was as simple as it was true: “the healthy have no need of a physician but the ill do.” Note that, for Jesus the “tax collectors and sinners” are not, in themselves, well. They are ill. They need help. They need saving. We should infer from his response to the Pharisees that he was not affirming their sin but neither did he refuse to engage them socially.
Matthew 21:31-32: Jesus and the two sons
“What do you think? A man had two sons. And he went to the first and said, ‘Son, go and work in the vineyard today.’ And he answered, ‘I will not,’ but afterward he changed his mind and went. And he went to the other son and said the same. And he answered, ‘I go, sir,’ but did not go. Which of the two did the will of his father?” They said, “The first.” Jesus said to them, “Truly, I say to you, the tax collectors and the prostitutes go into the kingdom of God before you. For John came to you in the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes believed him. And even when you saw it, you did not afterward change your minds and believe him ( Matt 21:28–32; ESV).
Were we to cite only v. 31 without considering vv. 28–30 and v. 32, we come away with one impression but when we consider v. 31 in context another rather different picture emerges. The question is about who is actually righteous and how. Who is righteous, he who professes but does not believe or he who sins, repents, and believes? Obviously, it is the latter. The believer, to whom God has graciously given new life, believes and because he believes he repents. That one is an heir of the Kingdom of God. Verse 32 is essential: “but you did not believe him”. According to Jesus the condition or instrument of salvation from the wrath to come is not good works but faith in Jesus the Son of God.
Again, what is affirmed here is not the sins of the tax collectors and prostitutes but their repentance and faith in the Jesus who saves sinners. The legalists would have us believe that one must clean up himself first before coming to Jesus. The theological term for this is nomism. Sometimes it is called preparationism. This was at the nub of the eighteenth-century debate between the “Marrow Men” (e.g., Thomas Boston and Erskines) and the legalist majority in the General Assembly of the Scottish church. They had been influenced by that notorious moralizer Richard Baxter, who rejected the Reformation doctrine of justification and sanctification as the consequence of justification. Like Rome, Baxter wanted people to be sanctified in order to be justified, i.e., right with God. On the opposite side, the libertines do not believe that repentance is necessary but Jesus teaches both: free forgiveness and the necessity of repentance.
According to Jesus it is sinners, e.g., tax collectors and prostitutes, who need to repent and believe. Those who have no sense of their sin do not realize their jeopardy and their need for forgiveness. The legalists want people to clean up themselves and the liberties seem to think either that moral improvement is undesirable or impossible. Neither the libertines and the legalists understand that the way of salvation is not “being good” or clean up one’s self but recognising the greatness of one’s sin and misery and trusting in Jesus the substitute for acceptance with God. According to Jesus (and Paul, Peter, John, et al.) getting “cleaned up” (sanctified) comes after or, to be more precise, as a consequence of the gift of new life, true faith in Christ, and repentance.
Jesus and the lost sheep
And to him were coming all the tax collectors and sinners to hear him” (Luke 15:1).
Luke adds immediately (v.2) that the Pharisees and scribes were offended by this. They complained, “This man welcomes sinners and eats with them.” The Pharisees and scribes were partly right. He did welcome and eat with them but again, both the legalists and the liberties draw the wrong inference. Jesus’ welcoming of sinners was not an affirmation of their sin. Jesus did not practise identity politics. He did not regard their sin as an immutable characteristic which could not or should not be changed. He regarded them as bearers of the divine image, who had fallen into sin, who needed to be saved. The legalists think that sinners are beyond salvation and the libertines deny that salvation is necessary. Both are wrong.
We know this from the context. Jesus tells a parable of the lost sheep. The tax collectors and sinners are lost sheep. The libertine approach is to say, “there is no such thing as a lost person”. Jesus disagreed. One point of the parable is that there are lost people and they need to be rescued from the consequences of being lost (i.e., damnation, another missing category for the libertines).
Against the legalists, Jesus came actually to save lost people. He is God the Son incarnate, who became incarnate for the express purpose of obeying on behalf of and saving all the lost sheep whom the Father had given to him (see John 17). Jesus affirms this way of thinking in the parable of the lost coin (Luke 15:8–10) and the parable of the lost son (Luke 15:11–32). Salvation is necessary and it is free by divine favour alone, through faith alone, in Christ alone.