All of Chapter 18 has been built to this lesson. This is a parable on its own, or a continuing illustration of the parable of the Lost Sheep, that serves as the corrective aspect of the lessons in the first half of the chapter about correcting the self. It is a hypothetical story, if/then, that teaches the lessons of the Parable of the Lost Sheep. The twelve apostles must learn to correct their own selfish pride … their childish desire for greatness BEFORE they are able to lovingly correct a ‘little one’ who is caught in an habitual sinful life. Discipline of the self involves obedience, modesty, and gentleness.
The context of Jesus’ words imply a situation in the body of believers when a ‘brother/sister’ [ἀδελφός (adelphos)] sins … but not just any sin … sins against you, a fellow brother/sister. The context is clear and Jesus intends this instruction to be for the relationships between the ‘children’ of his Church.
This action of ‘sins against you’ implies an habitual sinful lifestyle … an ongoing & unrepentant offense or mistreatment. Remember that the foundation of Christian fellowship and family is the eager ‘bearing with one another’ [Colossians 3:13]. We are to willingly endure with other believers despite differences and frustrations. We love & forgive one another despite our quirks.
This teaching is for the restoration of a ‘brother’ in Christ … this is the evangelism of a Christian. The person ‘won’ or ‘gained’ is not an evil pagan, but ‘your brother’. An important and often neglected part of evangelism is to win Christians to Christianity, to disciple disciples, to win the Church to Christ.