It is not surprising that Jesus encounters tax collectors in Capernaum, a border town to neighboring Gaulanitis. The Mishnah describes tax collectors making daily rounds, “exacting payment of men with or without their consent,” or, as here, sitting at tax stands with account books open and pen in hand (m. Avot 3:16). Travelers arriving in Capernaum from the territory of Herod Philip and the Decapolis to the east and north would be taxed by agents such as Levi, who were in the service of Herod Antipas, tetrarch of Galilee and Perea. The Roman tax system was complex and varied, even in a small country like Palestine. Land and poll taxes were collected directly by the Romans, but taxes on transported goods were contracted out to local collectors, most of whom were ethnic Jews but probably not observant Jews, since Torah-conscious Jews could not be expected to transact business with Gentiles.20 Levi was one of these middlemen (or in the service of one) who made bids in advance to collect taxes in a given area. His own profit came from what he could mulct from his constituents, and a portion of his receipts stayed in his own pockets.21 The Roman system of taxation depended on graft and greed, and it attracted enterprising individuals who were not adverse to such means.22

Tax collectors were obviously despised and hated. 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

The Pharisees, the most influential religious party in Palestine, were deeply devoted to the Mosaic Law. They strictly regulated their lives by the supposedly binding interpretations of it passed down in oral tradition and were meticulous about maintaining ceremonial purity (cf. 7:1–5). They criticized Jesus for not being a separatist, for failing to observe their pious distinction between “the righteous” (they themselves) and “the sinners.”