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Today is one of those days that I wish I was allotted more than 700 words! If you are interested in learning more about the Sermon on the Mount, I've written much more extensively about it here.
In the Beatitudes, as they're called, Jesus lists the identifying characteristics of the blessed and the blessings they can anticipate. If you look at those blessings closely, you'll notice that they are all various aspects of what the blessed will enjoy in the kingdom of heaven. Thus, by examining ourselves in the light of the identifying characteristics of the blessed, we can determine if we are on the road to heaven or not.
Have you recognized your spiritual poverty, mourned over your sins, and humbled yourself in repentance, now longing for righteousness (5:3-6)? Having received God's mercy, have you become merciful towards others (5:7)? Is your heart pure, so that your holiness is not just a thin veneer of religiosity like the Pharisees (5:8)? Are you working to help others make peace with God through repentance, even those who may persecute you for your righteousness (5:9-11)? If you can answer in the affirmative to those questions, you are on the road to heaven, blessedly transformed by God's grace.
The fact that holiness is the mark of true believers is further affirmed in 5:17-20, pivotal verses in this sermon. Jesus declared that unless our righteousness exceeds that of the scribes and Pharisees, we will not enter the kingdom of heaven. He elaborated on that theme in much of the remainder of His sermon, repeatedly exposing the unrighteous doctrine and practice of the scribes and Pharisees so that His followers would know how to do better.
The Pharisees were contentious, murderers at heart, and focused more on rituals than relationships; Jesus expects His followers to love each other dearly and reconcile when there is division, as love is the important thing (5:21-24). The Pharisees kept the letter of the law prohibiting adultery, but lustfully ignored the spirit of it, and divorce was rampant among them. Jesus expects much more from us (5:27-32). The scribes and Pharisees had invented elaborate means to justify lying (for more on this, see 23:1-36); Jesus expects us to always speak simple truth (5:33-37). By misapplying scriptures meant for judges in Israel's court system, the Pharisees justified taking personal revenge for the pettiest of offenses. Jesus expects us to be merciful even to our enemies, displaying a love that is superior to the world's, imitating our merciful Father (5:38-47).
Don't make the error that so many do when they read Jesus' oft-repeated statements, "You have heard that it was said...but I say to you..." Jesus was not correcting and contradicting Old Testament statements of His Father. He was not altering moral law. Remember, He declared early in His sermon that He had not come "to abolish the Law or the Prophets," but to fill them to the full (5:17). What Jesus was correcting was the false teaching of the scribes and Pharisees, who had twisted God's commandments for their own convenience. This is especially clear, for example, in Jesus' words, "You have heard that it was said, 'You shall love your neighbor, and hate your enemy'" (5:43). The second half of that statement was obviously the teaching of the scribes and Pharisees.
Do you want to be great in the kingdom of heaven? Jesus revealed the secret: Obey and teach the commandments (5:19). We will learn as we continue to study the New Testament that, under the New Covenant, we are to obey the law of Christ (which consists of all His commandments), rather than the Law of Moses, which was given to Israel alone (see 1 Cor. 9:19-21). This is not to say, however, that there isn't plenty of overlap between those two laws. Lust was a sin under the Old Covenant (see Ex. 20:17), and it remains so under the new covenant (5:28). Incidentally, loving one's enemies is not a new concept under the new covenant (see Ex. 23:5 and Prov. 25:21-22).
Clearly we see from today's reading that there is a relationship between holiness and heaven. Those who truly believe in Jesus obey Him.