Disciples or Pharisees: The Beatitudes vs the Woes of Jesus in Matthew

Jesus’ Beatitudes in Matthew 5 describe the kind of life he calls his followers into. It’s not what the religious people of his day or our day expect. What Jesus calls a “blessed” or “flourishing” life isn’t the kind of stuff that will make on the #blessed pics on Instagram. This picture of true vs false disciples becomes even more clear—and scary—when we read it alongside of his woes against the Pharisees in Matthew 23. While Matthew 5 paints a picture of true religion, Matthew 23 exposes false religion for what it is. We need to read both the beatitudes and the woes of Jesus to see the kind of disciples Jesus does and doesn’t want us to be. Together, these passages clue us in to what costly, compassionate, and Christ-honoring discipleship truly looks like.

Background to the Beatitudes: Sermon on the Mount

The Sermon on the Mount (Matt. 5–7) is Jesus’ description of the new kingdom-life he is bringing about as the King. These are not ways his followers are made right with God, nor are they strict rules his followers are kept in check by. Instead, the sermon offers more of a vision for the kind of kingdom Jesus inaugurates and the kind of kingdom-people who can represent and advance that kingdom. N. T. Wright describes the larger truth of the Sermon on the Mount as: “God’s future is arriving in the present, in the person and work of Jesus, and you can practice, right now, the habits of life which will find their goal in that coming future.”[1]

The Sermon on the Mount describes what a full and fruitful life with Christ can look like. Jesus is the King who aims to bring our lives back into God’s design, living in a way that is more fully human and leads to flourishing. The kind of flourishing (“blessed are…”) Jesus describes awaits his followers in full in the future age—the eschaton on the New Earth—but can be experienced and displayed in part even in this present age.

In his excellent book on this famous but often misunderstood part of the Gospels, Jonathan Pennington summarizes:

“In the first instance, the argument of this book will be that the Sermon’s answer to the human-flourishing question is that true human flourishing is only available through communion with the Father God through his revealed Son, Jesus, as we are empowered by the Holy Spirit. This flourishing is only experienced through faithful, heart-deep, whole-person discipleship, following Jesus’s teachings and life, which situate the disciple into God’s community or kingdom. This flourishing will only be experienced fully in the eschaton, when God finally establishes his reign upon the earth. As followers of Jesus journey through their lives, they will experience suffering in this world, which in God’s providence is in fact a means to true flourishing even now.”[2]

Jonathan Dodson offers this summary:

“Jesus’ sermon casts a vision for how we’re meant to flourish in this world. Pull on the heavenly promises, and you find character is attached in the present. The Sermon on the Mount provides a guide to the good life in both its everyday ethics and its eschatological promises. Like a pitchfork, it goads us to good action, but it also dangles a carrot: heavenly promises for present times. The sermon addresses habit by luring us with a glorious vision of existence.”[3]

The sermon calls for an authentic discipleship rather than external conformity or mere rule-keeping. Jesus wants people transformed by the inside-out. The Holy Spirit, not our will power, gives us new hearts that flow out into new ways of being and living.

Much of the Sermon is surprising. It doesn’t simply follow the religious conventions of the day, nor does it invent something not found in the Old Testament. Instead, Jesus sees himself as the fulfillment of what the Old Testament taught and pointed forward to. Jesus creates a a New Covenant people marked by spiritual renewal, faithfulness, and self-denial. Jen Wilkin reminds us how surprising this might have been to an original audience anticipating a King who brings them to power rather than call them to humility and mercy. “I suspect their visions of walking closely with Jesus involved being the strongest rather than the weakest, the greatest rather than the least, the first rather than the last. Jesus’ sermon would have completely toppled their eager hopes to reign and rule with him in power, popularity, and ease.”[4]

The Sermon on the Mount reminds us virtue matters. Our works don’t justify us, but good works flow from a transformed heart, a new identity, and a life of joyfully following our Lord. We aren’t yet what we one day will be, but we are not who we were. But we can be (imperfectly) a picture of what life with the King in his Kingdom looks like.

The Beatitudes

We often misunderstand both the beatitudes (Matt. 5:3–12) and the woes (Matt. 23:13–36) of Jesus. They are not simply the do’s and don’ts of Christianity. They’re not even behaviors that lead to immediate blessing vs cursing, but they are part of this virtue and wisdom language declaring the kind of life that leads to ultimate flourishing. They’re not to be read as a “do this to be blessed by God” in the sense of a reward, but they’re a description of wise, virtuous living. It’s how we are salt and light as Christ followers.

The beatitudes invite us into the kind of kingdom life fitting of Jesus’ followers in this world that prepares us to be useful and “flourish” here, while also preparing us for the kingdom to come. Those who mourn do find comfort in this life from God but will receive a full and lasting comfort in the life to come. We are “blessed” but much of that blessing awaits us in the eternal kingdom on a new earth.

“Jesus begins his public ministry by painting a picture of what the state of true God-centered human flourishing looks like. He is making an appeal and casting an inspiring vision, even as the Psalms, Proverbs, and Isaiah do, for what true well-being looks like in God’s coming kingdom.” Jonathan Pennington, The Sermon on the Mount and Human Flourishing

As with the Sermon on the Mount as a whole, there’s an emphasis on true righteousness and purity from the inner person over merely external actions and rituals. It also holds out hope that our ultimate “blessing” and vindication isn’t in this life or from this world but will be by God in the world to come. We might be despised now but will be favored later. It reminds us that the kind of people we are in this world might not be valued or of much importance to others, but it is of great importance to God. And what God considers good, virtuous, and Christ-like might be very different from how the culture, and even many within the Church, see it.

The Woes

While you might be somewhat familiar with the beatitudes, one helpful way to view them is through a comparison to the seven woes in chapter twenty-three of Matthew. The religious leaders in Jesus’ day are the subject of the woes, and the people are warned not to follow them. The religious leaders of Jesus’ day are more concerned about external religiosity, being seen, and having power. The religious leaders neglected the weightier matters of the law (like compassion and justice) and made small things into big things. They rejected God’s commands for human traditions. Their way of living and vision of the good life was more in line with the culture and surrounding nations than the vision of Jesus.

When you contrast the humility, meekness, selflessness, inner purity, compassion, and justice describing those in the beatitudes with the pronouncement of woes against neglecting these matters, it should give us a glimpse into what Jesus sees as a life of virtue and a life of vice. Vice can be cloaked in religiosity and have more to do with building myself up self than serving others.

When you read Matthew 5 and Matthew 23, it’s tempting to justify myself and think about where others fall short. But my encouragement is to read these two passages with an honest, humble reflection of your own life.

One thing that concerns me, and one thing I want to take serious personally, is that much of the Church in America today looks more like those in Matthew 23 than those in Matthew 5. Many in the Church are more concerned about their rights and privileges than laying down their rights and privileges for others. Many are concerned about their safety and prosperity but not as concerned about the prosperity and flourishing of others. Many give greater attention to external religious practices than an inner transformation. There’s a neglect of the “weighty matters” like compassion, justice, and faithfulness. Instead, of these weighty matters our attention is given to advancing or preserving power and material blessing for ourselves in this life.

When we compare Matthew 5 and 23 and see how the pull of human nature leads us to pursue more of the religion of the Pharisees than the humble, lowly religion of Christ’s beatitudes, we should feel the weight of conviction and caution. Jesus calls us to a kingdom not of this world. His values, beliefs, and practices look very different. They are not what the world’s values, but they lay before us how to enter into the “blessed” life with Jesus as well as how to reflect Jesus to the world.

Recommended Resources


[1] N. T. Wright, After You Believe: Why Christian Character Matters (New York, NY: HarperCollins Publishers Inc., 2010).

[2] Jonathan Pennington, The Sermon on the Mount and Human Flourishing: A Theological Commentary (Grand Rapids: Baker Academic, 2017).

[3] Jonathan Dodson, Our Good Crisis: Overcoming Moral Chaos with the Beatitudes (Downers Grove: InterVarsity Press, 2020).

[4] Jen Wilkin, “Why Study the Sermon on the Mount?”, https://www.thegospelcoalition.org/article/why-study-the-sermon-on-the-mount/

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You can follow me on Twitter or Instagram @IndyCrowe for the short & sweet stuff.

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