In Matt 9:10-13, the disciples of Jesus are asked why their master eats with tax-collectors and sinners. Both the question and the threefold answer are analysed in this study. Wisdom traditions prescribe Torah teachers not to engage with blatant sinners. This approach becomes contested in the first century C.E., as is clear from Pharisaic disputes on sinners and tax-collectors. In his answer, Jesus characterises himself as the divine doctor, who stirs the capacity to repentance by his sheer presence. The quote of Hosea functions as a legal justification of this strategy. Hos 6:6 points to the concept of good works, benevolent actions that save even blatant sinners.