So you lost in court and now they’re going to take the shirt off your back. How can you possibly win? Paul’s commentary on this kind of thing was that perhaps we lost before we even got to court. Did we let things go too far (1 Corinthians 6:7)? Did we fail to create peace, or were we actually at fault? It does not really matter. Jesus told his disciples how to really win in heaven’s eyes — give more than was asked for — go way above the settlement price (Matthew 5:40). If someone sues us for the shirt off our backs, we are encouraged to gift wrap our coat as well and give it away to the plaintiff. Does Jesus want us to be suckers who are taken advantage of, or does living generously really work?
We have all lent something which has not been returned, whether it be a book, lawnmower or money. It makes us reluctant to lend again. Jesus encouraged his disciples to lend to the borrower (Matthew 5:42) and not turn him away. Does this mean that we are to lend until we have no money? That is a natural conclusion, which leads some to criticize Jesus. He spoke of starting with one borrower, not an unlimited number. Our natural inclination is the opposite extreme, not to lend at all or with very few exceptions for family or close friends. It is that extreme that Jesus challenged his disciples to reconsider. He challenges us also to consider lending without discrimination. Naturally, there are boundaries and limitations, but perhaps we could think about starting with at least one, like Jesus spoke about.