In this sermon, part of the “Living Towards the Day” series on the Sermon on the Mount, Toby revisits the first three Beatitudes—poor in spirit, those who mourn, and the meek—set against Matthew 4–5’s context of downtrodden crowds longing for the Kingdom of Heaven.

Toby argues the Beatitudes are not a transaction (“do this to get that”) or advice, but an announcement of good news: the powerless belong to God’s kingdom, mourners will be comforted, and the gentle/humble who are taken advantage of will inherit the earth (drawing on Isaiah 41, Isaiah 40, Psalm 37, and John 11).

The message insists these promises are only good news if spoken by Jesus as king, and explains their fulfilment as “now but not yet”: immediate comfort through restored relationship with God via the cross and resurrection, ongoing comfort by the Holy Spirit and community, and complete comfort when Jesus returns.

Episode 05 | Matt 5:5 | Toby Dedden | 31/05/2026

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What you will learn

  • The Meaning of “Beatitudes”: Understand the linguistic roots, deriving from the Latin word beatus, meaning “blessed” or “fortunate”.

  • The Old Testament Roots: Learn how Jesus directly echoes Old Testament realities from Isaiah 41, Psalm 37, and Isaiah 40 to validate His listeners’ suffering.

  • The Triad of Comfort: Discover how God dispenses comfort instantly through the work of the cross, ongoingly through the Holy Spirit and the local church community, and ultimately upon Christ’s physical return.

  • True Community Identity: How a church centered around the love of Christ becomes a tangible, real-world home for the lonely and alienated.

  • 00:00 – Introduction & The Allure of Rags to Riches: Why we love stories like Harry Potter and Luke Skywalker, and the deeper longings they represent.

  • 03:03 – The Crowds of Matthew 4: Setting the historical context of the vulnerable, overtaxed, and diseased people gathering around Jesus.

  • 05:00 – Jesus Sees the Unseen: How the Sermon on the Mount begins with Jesus truly seeing the downtrodden.

  • 07:04 – Deep Dive: The Poor in Spirit: Understanding poverty of pneuma—the powerless who lack the strength to go on.

  • 09:04 – Deep Dive: The Meek: Defining meekness as gentleness and humility via Psalm 37, standing in contrast to the overpowering.

  • 11:34 – Deep Dive: The Mourners: Why an absence of mourning is natural, but the act of mourning is the correct response to a broken world.

  • 17:04 – What the Beatitudes Are Not: Clarifying why this text is neither a commercial transaction nor moral advice.

  • 18:43 – The Authority of the Speaker: Why Jesus is either a liar, a hypocrite, or the actual King of an breaking-in kingdom.

  • 22:00 – The Now and Not Yet of Comfort: How God provides instant, ongoing, and ultimate future comfort through His Spirit and community.

  • The Context of the Crowds: The people Jesus addressed weren’t just experiencing surface-level issues; they were socio-economically crushed, physically sick, and completely unseen by the earthly kingdoms around them.

  • Poverty of Spirit Means Powerlessness: To be “poor in spirit” means a lack of an internal life force (pneuma) to keep going, placing a person in a position where only God can provide.

  • Meekness is Not Weakness: Directly quoting Psalm 37, Jesus defines the meek as the gentle, humble, and overlooked whose backs are routinely used to prop up the wicked.

  • Grief Should Not Be Bypassed: While wanting an end to mourning is natural, experiencing grief is the correct, necessary response to living in a broken world outside of Eden. Jesus models this by creating space for tears before moving to restoration.

  • An Announcement, Not Advice: Jesus is not telling his disciples to “try and mourn more” or outlining a checklist to buy your way into heaven. The Beatitudes are a royal announcement that the Kingdom of Heaven is wide open to the broken.

Living towards the day: The Poor In Spirit, the Mourners, & the Meek’ (Matthew 5:5)

Here is the updated transcript, cleaned of filler words, false starts, and repetitions, and adjusted to UK spelling and grammar.

00:00:00 We’re in the series Living Towards the Day: Sermon on the Mount. We’re here for the whole term, and we’ve spent the last few weeks in the Beatitudes. Now we’re finishing off the Beatitudes. “Beatitudes”, by the way, I realise we haven’t said this, is just the Latin term for blessed. Beatus, I think it is, is the Latin term which starts the first line and the first word of every line of this poem that Jesus begins with. So, we’re finishing off the Beatitudes this week by going back to the start of the Beatitudes, looking at the first three statements that he makes. Let me pray, and then we’ll have a look.

00:00:42 Father, we thank you for this space and this time where we can come and be your people together. Thank you for this opportunity to open your Word, to see what you said to your disciples back then and what you’re saying to your disciples now, and I pray that you will work in us and change us to become like you. In Jesus’ name. Amen. We love a rags-to-riches story, don’t we? Aladdin, Eminem, Charlie Bucket. People who grow up less fortunate stumble upon some sort of success and eventually become a blessing to themselves and to other people. Harry Potter, Ed Sheeran, Kung Fu Panda. They are the stories that keep a 10-year-old girl up at night thinking, “Maybe I’ll get a letter delivered by an owl.”

00:01:51 And our world is full of them. The stories are captivating. Frodo Baggins, Luke Skywalker. They’re the stories that keep an 11-year-old boy trying to flick a light switch using the Force. I mean, he swears that it worked one time. But for some people, the stories also go a little bit deeper, not just surface level. It’s not just a hope of magic, but maybe the good news that we’ve been waiting for. Maybe there’s another world in which I belong. Maybe the 10-year-old girl is hoping for a home where there aren’t arguments every night. And maybe the 11-year-old boy is hoping that somewhere in the galaxy there are his people. And there are times when rags-to-riches becomes a true lived reality for some people. But they are the exception to the rule. And at some point, we’re forced to ask: are these stories just nice sentiment, or are they actually good news?

00:03:03 In Matthew’s Gospel, there’s some really important context before we get to chapter five, where Jesus brings the Sermon on the Mount. In chapter four, verse 17, Jesus has been travelling and preaching and proclaiming that the Kingdom of Heaven has come near. This is a place where people have been waiting and longing and desperate for the Kingdom of Heaven to come near. Through Jesus’ preaching, travelling, and works of healing, people start hearing about him and gathering around to see and listen to what he has to say. In the end of chapter four, verses 23 to 25 show the kinds of crowds that gathered. Verse 24 says, “People with various diseases, suffering severe pain, the demon-possessed, those having seizures and the paralysed.”

00:03:56 And verse 25 notes they’re coming from everywhere. But those are also not their only problems. These are people who have had their land disrupted and their work overtaxed for the benefit of the growth of a kingdom that they don’t belong to and they don’t thrive in. They have people around them who have more power, more prestige, and more sway than any individual. They are a people who are downtrodden and downcast, and around them is a kingdom that builds itself up on the backs of those who are lesser. These people gathering to hear Jesus are unseen. So, the talk of this longed-for kingdom of heaven and the potential that the promised Messiah has come—who their scriptures say will make all things new and will bring social, spiritual, and physical restoration—fills them with a longing. Could this be it? Could Jesus actually be the one?

00:04:58 And so they gather around, they bring their sick, and they hope; they come and they listen to him. That’s the context in which Jesus stands up and brings the Sermon on the Mount, beginning with this poem of the Beatitudes. Then we get to chapter five, and the first thing that’s said in this whole discourse is that Jesus saw them. He saw the crowds. He saw the unseen and the downtrodden, and what a difference even just that makes. It is as though his response to this ragtag, nomadic group of people is that he stands up and starts this poem. The Beatitudes is not just an introduction to the Sermon on the Mount; it’s an introduction to the Kingdom of Heaven. He starts by seeing the crowds and saying, “The poor in spirit, the mourners, the meek, the rags—you are the blessed ones. You are the fortunate ones because the kingdom of heaven is yours, because comfort will come, and because you will inherit the earth.”

00:06:30 Is this a rags-to-riches story? Because there are times where rags-to-riches stories are a reality for some people, but that’s the exception to the rule. At some point, we’re forced to ask: is this just a nice sentiment, or is this actually good news? Let’s go through each of these three statements and see if we can come to some sort of response to that question. “Poor in spirit.” Blessed are the poor in spirit. Literally, the poverty of spirit. If you’re familiar with the Greek, the word for spirit is pneuma. It can be translated, and often is, as breath, wind, or spirit. Behind this is the invisible life force behind something; that’s what connects all of those things. So, if you are experiencing poverty of pneuma, you lack the power to go on. This is why the Bible Project interprets the poor in spirit as the powerless.

00:07:59 As with all of the statements in the Beatitudes, this draws on Old Testament realities. The poor man in the Old Testament is one who is both afflicted and unable to save himself, and therefore he looks to God for salvation. Poverty goes beyond the financial. It’s the picture given in Isaiah 41 of the poor and needy who search for water, and there is none, and their tongues are parched with thirst. But God says about that person, “I, the God of Israel, will not forsake them.” Then he applies that aspect of poverty to the life force that drives someone—to the pneuma. Jesus is saying, “Blessed are the poor in spirit. Blessed are those who lack the power to go on and find themselves in a position that only God can provide for. Yours is the kingdom of heaven. You belong.”

00:09:04 Let’s jump straight to the third one and come back to the second one later: the meek. There are lots of different suggestions on what “the meek” means. There are a few other instances in the New Testament where that Greek word is used, and each time it’s translated differently in our English Bibles. When Jesus says, “I am gentle and lowly in heart,” he’s describing himself as meek; “gentle” is the same word there. When Peter uses it in 1 Peter, it’s translated as “humble”. Here in Matthew 5, we have “meek”. None of them are wrong. Meekness is gentleness and humility, but it’s also more than that. Thankfully, Jesus is directly quoting from the Old Testament, so we get some good context. He directly quotes from Psalm 37, which says, “The meek will inherit the land.”

00:10:27 The meek in Psalm 37 are contrasted all the way through the Psalm with the overpowering, whom David calls the wicked. Psalm 37:14 says, “The wicked draw the sword and bend the bow and bring down the poor and needy to slay those whose ways are upright.” But the meek, in contrast, will inherit the earth and enjoy peace and prosperity. The blameless spend their days under the Lord’s care. Gentleness and humility, yes, but also to the point of being taken advantage of. The meek are the quiet ones, the gentle ones, the overlooked, the unsought after, the ones whose backs are used to prop up the wicked, and the ones whose land is taken by a kingdom they don’t belong to. Blessed, Jesus says, are the meek, the unimportant, the gentle and humble, the used, and the ones who spend their days in the Lord’s care, because they will inherit the earth.

00:11:34 Then there are the mourners in the middle. Blessed are those who mourn. In some ways, this is a simple one; it is what it sounds like. I saw a video the other day of a man who started a small business that uses AI to simulate your loved one’s voice so that when they die, you can have phone calls with them. You upload a voice sample and some information, and AI assigns it to a phone number. When you feel the pang of mourning coming, you can dial a number and talk to them. Hannah Fry, the British mathematician, was interviewing this person and asked, “But isn’t grief necessary?” This was his response: “If we look at the devastation that grieving causes people—if we look at the disruption to our life—why would we not want to work toward grief not being a thing?” We might have mixed feelings about that. Grief and mourning do cause devastation and disruption, that’s true. How good would it be if there were no more? It would be so good.

00:13:00 I actually think that longing for grief and mourning to not be a thing is a very natural thing. David, in Psalm 13, cries out, “How long, O Lord? Will you forget me forever?” He wants this mourning taken from him; he doesn’t want it to be a thing anymore. “How long, O Lord, must I wrestle with my thoughts and day after day have sorrow in my heart?” He wants this mourning gone. To want an absence of mourning is natural because we were created for a world where mourning didn’t exist and the things that we mourn for never would have happened. But does that mean that we bypass it now? There’s something right about the act of mourning. Even though wanting an absence of mourning is natural, the act of mourning is also the correct response to brokenness. Think about Jesus in John 11, when his friend Lazarus dies. Jesus eventually raises him from the dead—it’s an incredible story and he knows he’s going to.

00:14:29 But before he does, he weeps. Mary and Martha, Lazarus’ sisters, come to Jesus. He could have stopped their tears by saying, “Don’t cry, guys. It’s all good. Just come with me to the grave, wipe your tears.” But he doesn’t. He creates space to allow them to keep crying, to keep mourning death, because that’s the correct response to brokenness. We might mourn the broken relationships that disintegrate over time, the slow decay of our bodies as age takes its toll, the chronic sickness of a spouse who longs for good health, or the death of loved ones—recent, long ago, young, old, unborn. We might mourn the hard heart of a friend whom you long to accept Jesus, or an injury or sickness you had where your body just hasn’t been the same since. All of these are products of brokenness, and they should be mourned. It is right to mourn them. Mourning these means mourning the fact that we live in a world outside of the Garden of Eden.

00:15:46 So here in Matthew 5, we have Jesus fulfilling what is said in Isaiah 40 when God says, “Comfort, comfort my people, and speak tenderly to them.” Then Jesus stands up, sees the mourning, and looks at these people who are experiencing the brokenness of the world. He says, “You are blessed. In the very thing that you wish did not happen to you, you are blessed.” Blessed are those who mourn, who feel the brokenness of the world and the fact that things aren’t as they should be; those who don’t bypass grief but recognise that mourning is right; those who follow Jesus through the grief of death in order to head towards the comfort and hope of resurrection and new life. Blessed are you who mourn, for you will be comforted. That’s the good news of the gospel. We will be comforted.

00:16:38 Is this a rags-to-riches story? There are times when rags-to-riches stories become real life, but they’re the exception to the rule. Jesus stands in front of a crowd of broken people and claims all of this, and surely at some point we have to ask: is this just a nice sentiment, or is this actually good news? I think it all depends on a few things. Let’s look at three questions to see if we can grapple with an answer: What’s the text doing? Who’s saying it? And when will it happen? First, what is the text doing? Let’s look at two things the Beatitudes is not. The Beatitudes is not a transaction. Jesus is not standing up and saying, “You can be saved if you’re a good person.” We hear that all the time: “I do, and therefore I will get.” He’s not saying, “If you just gentle yourselves a little bit, calm down, and become meek, then I’ll give you the earth.” He’s not saying, “If you become so destitute in your spirit that you would call yourself poor, then my kingdom is yours.” That doesn’t work in alignment with Jesus’ other teachings of repentance and faith.

00:18:12 It’s not a transaction. But the list is also not advice. Jesus is not telling his disciples what kinds of people to be, like, “You guys should mourn more,” or “You guys should be persecuted.” The Beatitudes is not advice, and it’s not a promise of transaction; it is an announcement of the good news of the Kingdom of Heaven. The second question is: who’s saying it? Because who can make that kind of announcement? Mahatma Gandhi, the Indian freedom fighter, loved the Sermon on the Mount. He read it when he was in London and thought, “Wow, Jesus is saying the exact things that I base my life on.” He was shocked to find that all that Jesus says lines up with his ideology of the world, and along with many other people, he recognised Jesus merely as a good teacher.

00:19:25 Let’s consider for a second if Jesus were merely a good teacher. If he were merely a good teacher, he would have no power to fulfill the claims that he makes. Inherit the earth—by whose authority? Comfort will come—how? These promises that he makes in this announcement would be nothing but empty. Secondly, he’s doing it in front of the most vulnerable and hurting crowd. Making empty promises to a crowd of people who are following him is not something a good moral teacher would do. That goes against almost every moral there is, especially the ones that he goes on to teach about in the Sermon on the Mount. So really, it wouldn’t make him a good moral teacher to stand up in front of the broken and say, “Yours is the Kingdom of Heaven.” It would make him a manipulative, lying, hypocritical orator, not someone to look up to. C.S. Lewis says there’s another option: that he’s a lunatic. We won’t deal with that one today.

00:20:47 The third option is that he really is who he claims to be. He really is giving an announcement of the good news of the Kingdom of Heaven because he really is the one who can. He really is offering the kingdom of heaven to those who are powerless. He really is making the unimportant and humble heirs of the earth. He really is promising comfort to those who feel the brokenness of the world because he really is the king of this new kingdom. He really is bringing all things back to how they once were in the Garden of Eden. So, is this just a nice sentiment, or is it actually good news? If Jesus really is the king, then this is not just a nice sentiment. It’s an announcement from the heavenly king that the kingdom of heaven has come near. Though we live among earthly kingdoms, we can still belong to an eternal one, and in this eternal one, those who are powerless, humble, and mourning truly are blessed.

00:21:56 But I still think there’s one more lingering question that we need to put our finger on: when does it happen? If this is true, why do I not have the earth? Why do I still feel like the poor in spirit and the unimportant? Why am I not comforted? Why am I still grieving the loss that I’ve experienced? When does it happen? Let’s take mourning as an example. We mourn the state of brokenness in the world, and there’s a promise of comfort. Is that merely future, or is it now? Theologically, we would say “now, but not yet.” Let me expand on that a little bit. There is an instant comfort that comes when we know Jesus. Whether that comfort is an experience that we feel or a truth that we believe, there is an instant comfort from the brokenness that we see around us and in us. This is because we believe that what Jesus did on the cross was take that sin on himself, pay the price of death, shed his blood, and break his body in order to bring peace back between us and God. There is an instant comfort even in merely knowing that the relationship is restored. Jesus’ resurrection brings life and ushers in an eternal era of life and joy.

00:23:40 But we’re not supposed to be free from mourning yet. To mourn is the right response to brokenness. So, there’s an instant comfort, but I also believe that there’s an ongoing comfort that we can experience. Just like Jesus makes room for Mary and Martha to fall to pieces, he does the same for us. Jesus is not in the business of bypassing grief, which is sometimes unfortunate for now, but he is in the business of redeeming it. He steps into the mess and the broken pieces, picks them up, and makes himself a home to dwell in. In John 14, the Holy Spirit is called the Comforter. The Holy Spirit reminds us of past and future truth; he works in our hearts to bring peace, restores our soul, and lives in the grief with us. Also, in 2 Corinthians 1, Paul says, “God comforts us in all our trouble so that we can comfort those in any trouble with the comfort that we’ve received from God.”

00:25:00 Part of his design is that we would also comfort each other once we have received comfort. I witness that here. I witness the comforting of each other and the pointing towards the gospel in distress. It’s this ongoing comfort, ongoing help within the community, and the ongoing work of the Holy Spirit that helps the 10-year-old girl whose house is full of arguments find a new home—not in an imaginary world, but in a community centred around the love of Christ. It helps the 11-year-old boy who wants to find his people somewhere in the galaxy find them here among this ragtag group of people. It is the broken relationships, the slow decay of our bodies, the chronic sickness, the death of loved ones, the hard heart of a friend, and the injuries or sickness being comforted both by the Spirit at work and the community around us. We point one another to the truth of the God of all comfort and towards a future of comfort to come.

00:26:16 God brings comfort to the mourning. Then, there is a time coming when Jesus will return, and this kingdom that we long for will be completely melded with earth again, just like it was in the garden, only better. There will be complete comfort, no fear of death, no fear of sickness, and no possible way for the cause of mourning to break in. There are times when the rags-to-riches story becomes real life, but they’re the exception to the rule. At some point, we’re forced to ask, “Are these stories just a nice sentiment, or is there actually good news?” The only way that there is actually good news is if the Beatitudes is an announcement, and it’s announced by the King of the kingdom that is breaking in. With the faith that God provides, I believe that to be completely true. I see no other option.

00:27:23 And so you poor in spirit, lacking the power to get by, you mourning the repercussions of brokenness and sin, you meek, unimportant, humble, and downcast—you’re blessed because yours is the kingdom, because you will inherit the earth, and because you will be comforted now in Jesus Christ, ongoingly by the Spirit of God and by one another. When he returns, every tear will be wiped away and comfort will be complete. I’m going to pray. Father, we thank you for Jesus. We thank you for sending him to come and bring the good news of the kingdom of heaven. We thank you that the news was not just spoken, but was brought to earth through what Jesus did. He went to the cross and took our sin and brokenness—that which separates us—and then he rose from the grave, defeating death. We thank you that now we can be in a relationship with you, part of this heavenly kingdom, experiencing the truth and fulfilment of these promises, Lord. Thank you that your kingdom is one that brings blessing to the mourners, the poor in spirit, and the meek. I pray, Father, that you would help us not to seek to bypass grief, but to seek you to restore it; not to seek to just crack on with a comfortable life, but to seek redemption in you. Help us to do that, not just individually, but with each other and for each other by the power of your Spirit. We thank you that that’s possible through what Christ has done. In Jesus’ name, amen.

  1. Rags to Riches Mentality: We love cultural underdog stories. In what ways do you subconsciously treat your faith like a “rags to riches” transaction, thinking you need to build yourself up spiritually before God will bless you?

  2. Owning Your Powerlessness: Being “poor in spirit” means recognizing you lack the strength to carry on by your own merit. What areas of your life are you currently trying to sustain with your own power rather than surrendering them to God?

  3. Allowing Space for Mourning: The modern world seeks to bypass or eliminate grief quickly (even inventing AI to simulate lost voices). How well do you allow yourself and others the space to mourn the broken realities of life, knowing that Jesus wept alongside the hurting?

  4. Becoming the Comforter: Paul writes in 2 Corinthians that we receive comfort from God so we can extend it to others. How can you practically step into the broken pieces of someone else’s mess this week to point them toward the hope of the gospel?