What does Matthew 5:42 mean?

Jesus provides another example of what it means not to "resist" an evil man. This is the standard of behavior He is setting for His disciples, and it must not have been an easy teaching to hear or follow. The overall idea is that followers of Jesus should overcome evil by freely giving of themselves more than the evil person wants to take. The picture He paints is someone targeted by evil, to be taken advantage of, and somehow the targeted person retains all the power in the exchange. If slapped on one cheek, offer the other. If sued for your tunic, give it and the cloak to your accuser. If forced to walk a mile by a Roman officer, willingly walk two or three. Overcome their evil with God's goodness (Matthew 5:38–41).

In this case, Jesus speaks of a different, but related scenario. The prior command implied someone with more power than us, such as a Roman soldier or a wealthier member of the community. This statement speaks of those with less power. Jesus escalates His earlier command by telling His followers to submit even to those on the lowest rungs of society.

To that end, Jesus tells His disciples to freely give to beggars and to loan money or possessions to whomever asks. These commands may feel like the weakest position of all: cooperating with an unreasonable request when it comes from someone with no power over you. Rather than an unfair insult, or an abusive command, this might be a manipulative or emotionally-tied appeal.

Jesus is demonstrating that choosing to give is a powerful act because you have chosen to do so. More importantly, you have chosen to trust God to continue to provide for you despite giving away what He has freely given to you. Just as Jesus' prior words don't prohibit legitimate self-defense (Luke 22:36), this command does not mean being naïve or gullible about charity (Matthew 10:16; 2 Thessalonians 3:10). It does mean that sacrificial, purposeful giving is the proper response when someone expresses legitimate need.