Anyone who is familiar with “moles” and informants in Nazi and Communist regimes will have an appreciation for the loathing that first-century Jews felt for tax collectors. The Mishnah and Talmud (although written later) register scathing judgments of tax collectors, lumping them together with thieves and murderers. A Jew who collected taxes was disqualified as a judge or witness in court, expelled from the synagogue, and a cause of disgrace to his family (b. Sanh. 25b). The touch of a tax collector rendered a house unclean (m. Teh. 7:6; m. Hag. 3:6). Jews were forbidden to receive money and even alms from tax collectors since revenue from taxes was deemed robbery. Jewish contempt of tax collectors is epitomized in the ruling that Jews could lie to tax collectors with impunity (m. Ned. 3:4)—a ruling, incidentally, with which both the houses of Hillel and Shammai (who normally stood poles apart) agreed. Tax collectors were tangible reminders of Roman domination, detested alike for its injustice and Gentile uncleanness. Not a few Jewish extremists, including one among Jesus’ own disciples (3:18), considered submission to the Roman yoke, as well as its system of taxation (see 12:13–17), an act of treason to God. – James Edwards
For by grace you have been saved through faith. And this is not your own doing; it is the gift of God, 9 not a result of works, so that no one may boast. – Ephesians 2:8-9 (ESV)
For consider your calling, brothers: not many of you were wise according to worldly standards, not many were powerful, not many were of noble birth. 27 But God chose what is foolish in the world to shame the wise; God chose what is weak in the world to shame the strong; 28 God chose what is low and despised in the world, even things that are not, to bring to nothing things that are, 29 so that no human being might boast in the presence of God. – 1 Corinthians 1:26-29 (ESV)
Ironically, in one sense great sinners stand closer to God than those who think themselves righteous, for sinners are more aware of their need of the transforming grace of God.
The scandal of this story is that Jesus does not make moral repentance a precondition of his love and acceptance. Rather, Jesus loves and accepts tax collectors and sinners as they are. If they forsake their evil and amend their lives, they do so, as did Zacchaeus (Luke 19:1–10), not in order to gain Jesus’ favor but because Jesus has loved them as sinners. – James Edwards