What does Matthew 5:44 mean?
ESV: But I say to you, Love your enemies and pray for those who persecute you,
NIV: But I tell you, love your enemies and pray for those who persecute you,
NASB: But I say to you, love your enemies and pray for those who persecute you,
CSB: But I tell you, love your enemies and pray for those who persecute you,
NLT: But I say, love your enemies! Pray for those who persecute you!
KJV: But I say unto you, Love your enemies, bless them that curse you, do good to them that hate you, and pray for them which despitefully use you, and persecute you;
NKJV: But I say to you, love your enemies, bless those who curse you, do good to those who hate you, and pray for those who spitefully use you and persecute you,
Verse Commentary:
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.
Verse Context:
Matthew 5:43–48 continues Jesus' teaching on love and humility, a part of the Sermon on the Mount. After commanding believers not to seek revenge in the face of insults, Jesus expands the idea of love to include one's enemies. Human beings naturally struggle with the idea of passively accepting persecution. We naturally recoil at the idea of expressing active love—in our deeds, not necessarily in our emotions—for those who hate and attack us. However, loving those who love you is easy; God's standards are higher.
Chapter Summary:
The Sermon on the Mount contains some of Jesus' most challenging teaching. It begins with the unlikely blessings of the Beatitudes. Jesus' disciples must do good works in order to be a powerful influence: as the salt of the earth and light of the world. The superficial righteousness of the Pharisees is not good enough to earn heaven. Sins of the heart, such as angry insults and intentional lust, are worthy of hell just as much as adultery and murder. Easy divorce and deceptive oaths are forbidden. Believers should not seek revenge. Instead, God intends us to love our enemies and pray for our persecutors. In short, we should strive to be perfect, as God is perfect.
Chapter Context:
Matthew 5 follows Matthew's description of the enormous crowds that were following Jesus (Matthew 4:25). One day, Jesus sits down on a hill to teach them, in an address we now call the Sermon on the Mount. He describes as blessed those who are poor in spirit, who mourn, and who are persecuted. Christ also explains how God's standards of righteousness go far beyond behaviors and speech; they also include our thoughts and attitudes. Meeting God's standards means perfection. Chapter 6 continues this sermon, with more examples of Jesus clarifying God's intent for godly living.
Book Summary:
The Gospel of Matthew clearly shows the influence of its writer's background, and his effort to reach a specific audience. Matthew was one of Jesus' twelve disciples, a Jewish man, and a former tax collector. This profession would have required literacy, and Matthew may have transcribed some of Jesus' words as they were spoken. This book is filled with references to the Old Testament, demonstrating to Israel that Jesus is the Promised One. Matthew also includes many references to coins, likely due to his former profession. Matthew records extensive accounts of Jesus' teaching, more than the other three Gospels.
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