What does Matthew 5:44 mean?

Jesus' long list of reversals in chapter 5 concludes with this one. His listeners had grown up under a partly correct teaching. God's Word does, indeed, command us to love our neighbor as our self (Leviticus 19:18). However, it seems that the religious leaders were also teaching that it was permissible—possibly even mandatory—to hate one's enemies (Matthew 5:43). Jesus again declares that God's intent for the righteousness of His people goes beyond selfishness and legalism. It implies something much more difficult and more like God Himself.

Instead of only acting in love towards neighbors, Jesus tells His disciples to love their enemies and even to pray for those who persecute them. Though few people live this out, in a meaningful way, the idea is deeply ingrained in western culture. Many modern people have heard this teaching, or variations on it, all our lives. That makes it easy to forget how radical the claim was, especially for those who live with daily threats from dire enemies, as did the first-century Israelites.

On one hand, becoming part of the Roman empire brought benefits. Rome typically did not destroy those they conquered—rather, they allowed relative freedom with a set of conditions. Israel continued to function as Israel in many ways, and they experienced a form of peace under Roman rule. That said, Rome ruled over conquered nations absolutely and severely. Dissent beyond the established limits was savagely punished. Crucifixions were common and brutal. Roman soldiers enjoyed privileges and took liberties with Jewish citizens under their thumb. The Roman tax burden left many people in near poverty. The Jewish people understandably viewed Rome as their enemy.

And yet, a man thought by many to be the Messiah, the Savior who was supposed to free Israel from her enemies, has just commanded His disciples to love and pray for their enemies. Worse, He equated this with the righteous living needed to enter the kingdom of heaven. This is hard enough to grasp today, but at the time the words were first spoken they would have been shocking.

Christ does nothing to take the edge off this command, either. This is not described as emotional love, or affection. This kind of love is meant to be expressed in action. Offering prayers to God for people who are actively hurting you, especially for being associated with Christ, requires looking at the world in a completely different way. Jesus will escalate the difficulty of His command in the following verses.