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I was taught in seminary that the Sermon on the Mount (Matthew 5 to 7) wasn’t one sermon of Jesus’, but a collection of his sayings that Matthew assembled and that I was to obey. It was confusing to me. I saw the highest ideals of morality in attitude and behavior and the best advice for a good life and yet I knew I couldn’t “Be perfect as your Father in heaven is perfect” (Matthew 5:48). All I knew to do was to try hard to do what I should and ask God to forgive all my shortcomings! At that point I didn’t know how to become the kind of person who would obey Jesus from my heart — until Dallas Willard taught he how to read the Sermon on the Mount. (See his classic, The Divine Conspiracy.)
This is Jesus’ Greatest Teaching and it is based on a divine order that makes obeying his teaching possible. It’s a life-changing paradigm that many Christians are missing.
Understanding the beatitudes is the key that unlocks Jesus’ wisdom. Let’s pick up this key and open the treasure chest of the Sermon on the Mount. Dallas says that from start to finish in his sermon Jesus is not giving us commands, but illustrations of the blessings of living under God’s rule.

Jesus’ Tour of Life in God’s Kingdom

Let’s imagine that Jesus is giving us a guided tour of what life is like in the Kingdom of the Heavens. (The thoughts that follow are inspired by the opening of Dallas’ talk, “Knowing Christ Today” given at Bel Air Presbyterian Church in 2009.) We’re walking along with our Lord he’s showing us different kinds of people who are living under the Father’s loving rule.
Beatitudes
For instance, Jesus shows us some people who are living in poverty: they don’t have any money and yet they’re happy! You scratch your head wondering why. Then you hear the poor saying things like, “The Lord is my shepherd; I shall not want.” Or, “I don’t have any money, but I have the Lord — he’s good to me and his hand is at work in my life.”
Next Jesus points out some people who are grieving — a loved one has died or their business has failed or a family member has turned against them. They are sad because of what they’ve lost and perhaps because God has not answered their prayers the way they want him to and yet they smile with happiness. “How can this be?” you ask. Jesus answers, “They have found comfort under the wing of the Lord.”
Become Free of Anger and Lust
You continue walking along with Jesus, meeting all kinds of people. Over here you’re surprised to find some people who don’t get mad or resentful even when they’re mistreated. They’re quick to forgive and at the same time they’re free of shame and fear. They don’t use anger to get what they want — they are at peace. You realize that they too are in God’s kingdom and that’s why they’re blessed even in unfair circumstances.
Then you find some people who don’t cultivate lust and sensuality — even if they haven’t been able to find a spouse or are stuck in a disappointing marriage. Instead of lusting for what they don’t have they are content and happy with God and what he provides for them. And you say, “Well, I didn’t see that in the advertisements — I thought I needed a Lexus!”
Be Honest and Genuine
These people are radically different from most people in the world! And there’s more. Jesus points out some people who tell things exactly like they are — no exaggeration, no song and dance, no pressure. They don’t try to get people to do things. They simply speak the plain truth to others in a calm, matter of fact way.
Then Jesus says, “Look over here. These are people who don’t do their good deeds to be seen by people. They’re not trying to impress anybody by how they look or act — they’re just simple, ordinary folk.” You say, “My goodness, nobody is praising them, but they hold their heads high. How is it that they could have such confidence?” Jesus answers, “They’re looking to their Father who is secret and he rewards them openly.”
Don’t Judge
Following Jesus, he shows you some people who don’t judge other people. They don’t criticize the faults of others. They don’t engage in gossip or slander. And they don’t try to “fix” other people or get them to do what they “should.” Instead they accept people where they’re at, think the best of them, and say positive things about them. And if they want something from people or from God they simply ask politely. They live humbly and joyfully under the care of God.

Training with Jesus

These and the rest of the people in the Sermon on the Mount are able to be the kind of people that Jesus describes because they live with his spirituality. They go to God through grace of Jesus Christ, his death and resurrection on their behalf, and they trust God as he does, apprenticing themselves to him. Jesus is their Lord and Savior and their teacher/coach that they train under.
In the book of Acts we see Jesus’ followers living as bi-habitational creatures, “in the world, but not of the world.” The blessed and fruitful supernatural life in Christ that they demonstrate is for us too! The Sermon on the Mount lays out the path.

Jesus’ Greatest Teaching

My studies in Jesus’ Sermon on the Mount and Dallas Willard’s The Divine Conspiracy which unpacks it led me to write a paraphrase of the whole text of Matthew 5 to 7. What a meditation this is! You’ll love it! I  put this into a booklet which features a coaching tool, soul talk questions, and experiments for personal devotions or small groups. For just $3.99 you can have a copy of Jesus’ Greatest Teaching.