The Upside Down Kingdom: An Introduction to the Sermon on the Mount

The Upside-Down Kingdom: An Introduction

When I first became a Christian, I very quickly learned the acronym, WWJD? (What Would Jesus Do?). That was the question, and still is the question, followers of Jesus are trying to answer? How in the world are we to live this life as Christians? What are we supposed to do? Why are we supposed to do it? What are we allowed to do, and what are we not allowed to do? Where is the line? And so we made rules and lists for ourselves, “don’t drink, don’t chew, don’t go with girls that do”. Many traditions banned dancing and alcohol, while others focused on R rated movies, secular music, and dating. And maybe there is wisdom to some of these prohibitions, but the truth of the matter is that while everyone was making lists and getting caught up in the dos and don’ts of Christian living, we lost sight of what was to shape our lives as followers of Jesus. The question wasn’t altogether bad. We should want to know what Jesus would do in any given situation, and as His followers, we should seek to do the thing that we believe He would do. But getting at that answer has proven difficult for many in the church. And this is where the Sermon on the Mount comes in.

The Sermon on the Mount presents Jesus’ followers with something that is categorically other-worldly; it is a paradigm for Christian living that rubs against all common sense and conventional wisdom because it presents the moral vision of a kingdom that is “not of this world”. This is key for us to understand as we embark on this journey throughout the Fall; the Sermon on the Mount is a new law given from a new world to shape a new people to live as “elect exiles” in this world, so that onlookers might catch a glimpse of the beauty and truth of the new world and its King. Jesus is the point of the Sermon, but that point is not so much a period, as it is rather a comma, because the rest of the story pushes forward and is being written through the faithfulness of His followers. And this is where we find the answer to our questions above? What would Jesus do? Maybe it’s better to ask, “what did Jesus do?” He did the very things he is calling us to do in the Sermon, and He is doing it with a power that is not of this world, which He gives to us through His Spirit, so that we too might walk the path He has laid out for us: A Kingdom shaped life that turns all that we believe to be true on its head, providing a new and better way that leads to the flourishing of humanity and the glory of God.[1]

The purpose of this essay is to lay some tracks to run on as we travel through Jesus’ Sermon on the Mount. First, we will look at the historical, literary, and Old Testament context surrounding the Sermon. Second, we will define some key terms found throughout the Sermon, which will provide us with more context, both biblically and historically. Finally, we will discuss the grace filled demands the Sermon places on our lives today as we seek to follow Jesus in Ocean County and beyond.


Matthew’s Gospel: In the words of Patrick Schreiner, “The Gospel of Matthew is best understood with one eye looking back to the old story, and the other attuned to shifts in the new story”.[2] In other words, we need to wrap our minds around the Old Testament backdrop if we are going to fully understand Matthew, and in particular, if we’re going to fully understand the Sermon on the Mount. But before we get there, let’s get some introductory remarks out of the way. The Sermon on the Mount is not the whole story; in fact, it is a piece of the whole. In other words, the Sermon “belongs to a book apart from which it was never intended to be read”.[3] To read the Sermon on the Mount, one must understand the broader context of Matthew’s gospel.

Matthew’s gospel is the first book of the New Testament. Tradition holds that this gospel account was written by Matthew (formerly known as Levi the tax collector). Although he never identifies himself as the author, there are a number of reasons why his authorship is probable.[4] According to New Testament Scholar R.T. France, “the contents and tone of the gospel (including the “love-hate relationship with Judaism) seem to make…someone like Matthew as likely a candidate as any”.[5] There is debate surrounding the dating of Matthew’s Gospel, but conservative scholars tend to place it prior to AD70, “while the temple was still standing”.[6] This means that Matthew is presenting his gospel to a people who still have connections to the temple, the sacrificial system, and for all intents and purposes, the Mosaic Law. This makes his content that much more explosive, especially to those of Jewish descent, as Matthew is dismantling categories and traditions one by one.

Along with the historical setting of Matthew, how he structures his gospel also tells a story. Beginning with a genealogy that takes Jesus’ lineage all the way back to Abraham and identifying Him as a son of David, Matthew is showing that Jesus serves as the fulfillment of Israel’s story. Below are some examples of the Old Testament backdrop of Matthew and the Sermon on the Mount.[7]

Jesus as Isaiah’s End Times Prophet: The allusions to the Old Testament throughout the Sermon are numerous. Broadly speaking, Matthew is setting up Jesus as the fulfillment of Isaiah’s prophecy. As the Spirit rests “upon” Christ at his baptism, Matthew is alluding to Isaiah 42. Additionally, the quotations from Isaiah 9 in Matthew 4 present Jesus as the child upon who’s shoulders the governments of this world would rest.

Zooming in, the sermon itself alludes to Isaiah throughout The Beatitudes. The focus on the mourning and the poor are key themes drawn from Isaiah 61. In showing Jesus as the fulfilment of these Old Testament figures, Matthew is outlining Jesus’ historical authority, and showing how he is not a novel or new idea thrust “on humanity’s religious landscape, [but] he is rather the goal of a story, the history told in the Jewish Bible”.[8] Dale Allison further argues that “Jesus is the anointed [messianic] one prophesied by Isaiah 61, [and that] he has been sent by the same God who spoke to Abraham, Moses, David, and the prophets”.[9] This means that there is “continuity between the new and the old, and that ultimately the one who speaks here through his anointed [messianic] prophet is the one whose words and deeds constitute the religious story of Israel”.[10] In other words, Jesus is shown to be the one to bring Israel’s story to its glorious fruition.[11]

Jesus as the New and Better Moses: It is almost unfair how obvious this is for those who take the time to read the text slowly and closely. The Sermon begins with the following words: “When he saw the crowds, he went up on the mountain, and when he sat down, his disciples came to him”. The phrase, “he went up on the mountain” is lifted directly from the Moses narrative of Exodus, where he goes up on the mountain to receive the Law of God (cf. Ex. 24).[12] Furthermore, “Jewish tradition spoke of Moses sitting on Sinai”, so it appears that Matthew is borrowing, not only from the Old Testament tradition, but the broader Jewish tradition as well.[13] Again, paying attention to the broader context, Matthew draws even more parallels between Jesus and Moses:

  • A call from Egypt (Mt. 2:13-15)
  • Slaughter of the infants (Mt. 2:16-21)
  • A passage through water (Mt. 3:13-17)
  • A time of wilderness testing (Mt. 4:1-11)
  • Delivering the Law from a mountain (Mt. 5-7)

While Matthew is clear that Jesus is in fact the “better Moses”, New Testament scholar Dale Allison argues that this is not necessarily the main point; in “Matthew’s world, ‘Moses said’ was the equivalent of ‘God said.’ So to make Jesus one like Moses was a way of saying that…Jesus’ word is God’s word…the parallels with Moses are intended to exalt the authority of Jesus to make him a dispenser of divine revelation”.[14] In other words, to be like Moses is to be one who speaks with authority, the very words of God. And it is the authority of the speaker that makes the Sermon that much more radical and revolutionary; God is asking his followers to structure their lives in a way that contradicts conventional wisdom, to pursue a wisdom that is otherworldly, upside-down, which is the proper means to the flourishing of humanity. Furthermore, Matthew’s gospel is structured around five sections, containing both narrative and direct teaching. These sections are marked by the phrase, “and when Jesus had come to finish”, marking the conclusion of each of his teaching sections within the book. These five sections are intentionally placed throughout the course of the book and some have argued that they further connect Jesus to Moses, as Matthew contains a new Pentateuch or Torah.[15] See P. Schreiner’s TGC article for further links between Moses and Jesus in Matthew’s gospel.

Jesus as the New and Better Joseph: Patrick Schreiner does a great job of unpacking this in his TGC article, but we’ll cover a few things before moving along. Schreiner argues that Jesus’ birth narrative is “described from Joseph’s point of view, [and that] it’s revealed to him in a dream that this child [is] from the Holy Spirit [and] will save his people from their sins”.[16] It is no accident that “there was another Joseph who had dreams”.[17] Matthew is setting up Joseph, Mary’s husband, as a new and better Joseph. But that is not where the story ends. Matthew’s Gospel also portrays Jesus as the new Joseph.

  • Both are chosen by their father (cf. Gen. 37:4; Matt. 3:17)
  • Both are rejected by their brothers (cf. Gen. 37:4; Matt. 20:18)
  • Both undergo suffering and exile (cf. Gen. 37:17-20; Matt. 2; 27:27-31)
  • Both are exalted in a foreign court (cf. Gen. 41:39-41; Matt. 27:27-31)
  • Both turn and forgive their brothers who betray them (cf. Gen. 50:17; Matt. 26:28)
  • Both save their people (cf. Gen. 45:7; Matt. 1:21; 27:41-42).[18]

In other words, the story of Israel is finding its telos or fulfillment in the person and work of Jesus, and Matthew is taking every opportunity to demonstrate that for his readers. All of this is to show that the one teaching and performing good works and miracles throughout the narrative is the one who is teaching and working with the authority of Yahweh himself. The sermon begins with authority, and as he finishes speaking the text reads that “the crowds were astonished at his teaching, for he was teaching them as one who had authority, and not as their scribes” (Matt. 7:28, 29).

Finally, to further demonstrate that the Sermon should not be read in isolation, we see that Jesus not only preached these words, but he also lived them. Allison argues that “The sermon is a way of preaching Christ”,[19] and that Matthew’s Gospel shows Jesus himself living out the imperatives found throughout the Sermon. Another way of putting it is that “the commander…embodies the command”[20] A few examples are as follows:

  • Jesus blesses the meek (praus), a term later used of himself in Matt. 11:29 and 21:5[21]
  • He is a source of mercy throughout his ministry.
  • Matthew shows him as “being faithful to the Torah [the Law]” (cf. 8:4).[22]
  • He honors his own prohibition on oaths in 26:63-64.
  • parizo – to strike, appears twice in Matthew: in the “turn the other cheek” command, and when Jesus himself is “struck” and spat on while before Caiaphas and the council.[23]
  • In Matthew 6:5-6, he instructs the people in prayer, calling for privacy and simplicity in prayer, which he practices in both Matthew 14 and 26.

Defining Terms: In this section, we will look at some key terms found throughout the Sermon on the Mount. The goal is to clarify meanings where our western lenses and language could muddy the waters.

Makarios/Blessed/Flourishing: What in the world does that mean? This is the term that is found throughout the beatitudes in the first section of the Sermon. In most of our translations, this word has been translated as “blessed”. Many of us use this term, and even popular culture uses the term. Simply type #blessed into Google, and you will see how our culture understands “the good life”. But Scripture takes a different posture. In fact, Scripture provides two ways to understand our english word “blessed”, and our goal is to get at what Jesus had in mind as he peppered the term throughout the beatitudes (5:2-11). But there is a problem. The english word “blessed” conveys something that Matthew was never intending to convey. The historical and Old Testament context of the Sermon on the Mount places it at the nexus of two worlds, both seeking to understand how they might reach a point of success or “flourishing”. The Jewish world and the Greco-Roman world, and every other society leading up to and following, were asking the question of how humanity can succeed, or how we might “flourish”. In other words, how can we live what has commonly been called “the good life”?

Using the backdrop of the Old Testament, the beatitudes seek to answer that very question. Let’s get a little bit technical for a moment. The term makarios is a term that is used throughout the Greek translation of the Old Testament. It is used to translate the Hebrew word asre, which is “found especially in the Psalms and Proverbs. It is particularly appropriate there because it is a poetic and wisdom-related word”.[24] In other words, makarios is a term that deals in wisdom, describing “the happy state of the one who lives wisely”.[25] This means that when we approach the beatitudes, we are approaching a genre of literature known as Jewish wisdom literature. But there’s more, the term in the immediate context of the Greco-Roman world was used to describe “human beings who lived a life of happiness like that of the gods, meaning that their lives are beyond care, labor and death”[26] (I.e., god-like). But nowhere is this term associated with the sort of blessing that comes directly from the hand of God. Rather, the sort of blessing being dealt with in the beatitudes, and throughout the Proverbs and Psalms, is a blessing that one commentator describes as a “ground-up” blessing.[27] In other words, the world has been sovereignly designed in such a way that when one lives their lives in accordance with its design, their life will flourish.

And this is where we begin to ask questions, because the beatitudes do not necessarily fit in line with what we might call “the good life”. In fact, it seems to describe the very opposite of what any of us would describe as “good” or “blessed”. Even Christians tend to think more in line with the #blessed crowd, because we’ve been conditioned by culture, especially our American culture, to see happiness, fun, and pleasure as the end all and be all of our existence. But we need to remember that Jesus is inaugurating or beginning something new, and with this inaugurated kingdom comes a moral vision that is unlike anything the world has ever seen. Yes, the understanding of flourishing that results from a particular way of life was, and still is, common place, but it is the sorts of people being described in the beatitudes who receive this sort of blessing that creates the confusion and cognitive dissonance that characterizes much of Jesus’ teaching. The meek, the poor in spirit, those who demonstrate mercy, those who mourn, and those who are “persecuted for righteousness sake…[who are] reviled”, these are the ones who are said by Jesus to be the blessed ones, the flourishing ones, the ones participating in “the good life”.

What Jesus is doing, and what Matthew is capturing for the church, is showing us that our lives as Christians, as those who have been marked by the crucifixion of Christ, and called to suffer and sacrifice on behalf of others, are the ones who are keeping in step with the true story of the world. We are the ones who will receive the eschatological riches of comfort, inheritance, satisfaction, mercy, a vision of God himself, adoption and the kingdom of heaven. And this is the irony of the Sermon on the Mount, and the confusion it ushers into the world. The “good life” is a life that disrupts the status quo and provides hope for the suffering world of which we are apart. The kingdom of heaven is on a collision course with the kingdoms and powers of this world, and we are “blessed” to go along for the ride.

Teleios/Perfection/Whole or Complete: Matthew 5 closes with a command to “be perfect, as your heavenly Father is perfect”. Christians have wrestled with this verse for quite some time, and understandably so. Being perfect is something that is beyond anything we can aspire to. The term itself suggests a moral flawlessness that is at best out of reach, if not down right condemning.

The term in question is the Greek word teleios. In order to understand its meaning, we need to look at how the term has been used throughout the Greek translation of the Old Testament and other places in the New Testament.[28] From there, we can determine the range of meaning behind the term. Jonathan Pennington has done that work for us: Teleiosity [or perfection] in the Old Testament is “1. The idea of wholeness or completeness; 2. The giving of oneself to God wholeheartedly, akin to righteousness; 3. Wholehearted dedication that is demonstrated in obedience to God’s will, the idea of walking with God”.[29] With this as the literary and historical backdrop, Pennington argues that “The call to teleiosity in Matt. 5:48 and throughout the Sermon is the same call to ‘holiness’ that we see throughout the Old Testament…not moral perfection, but wholehearted orientation toward God”.[30] In other words, we are called to have a wholehearted devotion to God, but we are also called to have a wholehearted devotion to our neighbor. In the same way God postures himself toward his enemies, “while we were yet sinners, Christ died for us”, likewise we are called to the same radically natured love, which is why this call to be perfect closes out the section on loving one’s enemies and giving to those who steal from us. Jesus is calling his followers “to be ‘perfect in love’ or to ‘love completely’ in the sense that they are to love not only fellow Jewish neighbors but also enemy neighbors”.[31] This is a command that might rub us the wrong way, especially in our current cultural moment where different groups and tribes are pitted against one another. But the calling of the Kingdom should shape us, that we might manifest something different from the world around us.

Dikaiosyosne/Righteousness: Another term I want to cover is the word behind our english term, “righteousness”. There are massive amounts of debate surrounding this term, so understanding Matthew’s usage is key to gaining a fuller understanding to the Sermon. The term comes up right in the beginning of the Sermon, as the blessed ones are “those who hunger and thirst for righteousness” (5:6). What in the world is Jesus getting at here? What sort of righteousness is in view? Being that the Sermon is part of this kingdom inauguration, this needs to weigh heavily as we seek to determine what is being said. But first, what is the Old Testament background of the term? The Hebrew behind Dikaiosyosne is the term saddiq or “justice”. This is a covenantal justice that deals with God’s desire to “set the world to rights”.[32] The historical backdrop then means that Matthew is not necessarily referring to the theological category of imputed righteousness or the Christian’s individual justification, but rather, to the sense of justice that followers of Jesus ought to possess as we observe a world ravaged by injustice.

The “righteous” person, or the “blessed” person, is the person who is currently experiencing the “wholeness” or “flourishing” of the Kingdom of God. They are the one who has postured their life in such a way, that coincides with the design of creation, so that they are experiencing resurrection life in the here and now. And the irony of this, is that resurrection life, the “whole” and “flourishing” life, is experienced as followers of Jesus live their lives for the good of those around them in the name of the resurrected king! We are the means by which those on the receiving end of injustice might get a taste of the glory of the Kingdom of God, whether that is our work with our local crisis pregnancy center, providing help and counsel to those struggling with addiction, or any other way we breath life into those at death’s door, whether physically, emotionally or spiritually. To desire “righteousness” or “justice” is to desire the flourishing and holistic prosperity of those around us, which typically comes at our own expense.

Grace and the Sermon on the Mount:

In a tradition that has been so marked by the grace of God, we can approach texts such as the Sermon on the Mount with skepticism. Why all the requirements? Why all the demands? I thought we were saved by grace. Once again, looking at the context will allow us to properly understand what we’re looking at. Dale Allison sees this dilemma, and he makes an important observation:

Before Jesus makes any demands, he shows his compassion by healing the sick among the crowds. The act is pure grace, for the crowds have done nothing. The implicit lesson is that grace comes before task, succor before demand. Jesus’ first act is not the imposition of difficult imperatives but the selfless service of others. Today’s command presupposes yesterday’s gift.[33]

In other words, deliverance comes before the law. The mirroring of the Exodus narrative is in view here, as Jesus delivers people from the enslavement of “various diseases” and the “oppression of demons” (4:23, 24), he is echoing Israel’s deliverance from the enslavement and oppression of Pharaoh. And in like manner, following these acts of grace, he provides the people with a law, and in this case a new law that will serve as a conduit by which the people of God can experience resurrection life in the here and now.

In addition to the deliverance which precedes the Sermon, Jesus begins his talk with the beatitudes. This section is not so much a call to action, but a pronouncement of blessing upon those who are already living their lives in a certain manner. It is a pronouncement of encouragement amid poverty, comfort to those who are mourning, and inheritance and adoption to those who possessed nothing under this present evil age. It is with this understanding that we must engage the commands found throughout the Sermon, that we have been lavished with the grace of God, being delivered from our sins, and offered consolation amid the burdens and difficulties of this life. It is in light of this grace that we are called to live our lives shaped by the kingdom of God, so that we, and those around us, might get a taste of the “good life”, as we are used by God as a conduit to deliver resurrection life into the world around us.


As we close, the questions regarding how we are supposed to live our life should begin to make more sense. Looking at the Sermon, we are going to see that there is a goal to this life, and that goal is a kingdom shaped goal. It is a life that gives of itself, so that others might live. It is a life that is marked by love and grace, so that the world might catch a glimpse of what God is like. As stated above, the Sermon on the Mount is a new law given from a new world to shape a new people to live as “elect exiles” in this world, so that onlookers might catch a glimpse of the beauty and truth of the new world and its King. And the life we live as “elect exiles” is a life that is moving toward wholeness and perfection. The entire created order will flourish through the resurrection life of Jesus flowing through the veins of his body, the church. We are a people, called to be wholly devoted to Christ, in such a way that it causes onlookers to be radically confused, while at the same time, unexplainably jealous of what we possess as sons and daughters of the living God.  


[1] To be shaped by the kingdom is to be shaped by a king. The life, death, burial and resurrection of Christ provide us with the example and power to live our lives in a way that is shaped by his kingdom. When we think of the Kingdom of God, or as Matthew puts it, the Kingdom of Heaven, we should understand it as the rule and reign of God. This means that we are to live our lives in light of the fact that Jesus is seated on the throne, ruling over all of creation.  

[2] Schreiner, Patrick, “Matthew’s Gospel as You’ve Never Read it Before”, The Gospel Coalition Blog (, Sept. 2019.

[3] Allison, Dale, The Sermon on the Mount: Inspiring the Moral Imagination, Herder and Herder Books, New York, NY, 1999, pg. 9.

[4] Hendrickson, William, Matthew (pgs. 92-97).

[5] R.T. France, NICNT, The Gospel of Matthew (pg. 15).

[6] Ibid, 19.

[7] The following section uses content from Dale Allison’s commentary on the Sermon on the Mount and Patrick Schreiner’s Gospel Coalition article on Matthew’s Gospel.

[8] Allison, 16.

[9] Ibid. 

[10] Ibid.

[11] Important to note, Matthew begins his gospel with a genealogy that stretches back to both David and Abraham. This is key because it places Jesus in the line of both the Patriarchs and the Davidic dynasty. From the beginning of Matthew’s gospel, he is situating Jesus as the telos, or goal of Israel’s story.

[12] The Greek translation of the Old Testament, the Septuagint (LXX) was one of the New Testament writer’s primary texts. This means that often, when alluding or quoting the Old Testament, they would have been alluding or quoting the LXX. This does not mean that they did not also cite and allude to the Hebrew scriptures, but more often than not, it was the Greek translation.

[13] Allison, pg. 17.

[14] Ibid, 19. 

[15] The Pentateuch or the Torah are the first five books of the Bible, which were written by Moses. It appears that Matthew is using a literary device to further link Jesus to Moses, further identifying Him as the fulfillment of Israel’s story. Moses composed five books of law, and now Jesus is presenting five separate teachings.   Additionally, what is being put forth throughout Matthew is this idea of a “new law”, which is what the church needed to flourish as the people of God. See The Bible Project’s video on Matthew to gain a little more insight into the view that Matthew is providing a new Pentateuch for the people of God:

[16] Schreiner

[17] Ibid. 

[18] Ibid. 

[19] Allison, 19.

[20] Ibid, 20.

[21] Praus - πραΰς is used throughout the psalter, focusing specifically on those who will be exalted; it is used twice in the final eschatological section as well (24:9; 33:3; 36:11; 75:10; 146:6; 149:4)

[22] Allison, 20.

[23] The term is also used in Isaiah 50:6, one of the servant songs, where the innocent is beaten.

[24] Ibid, 44.

[25] Ibid.

[26] Ibid, 46. 

[27] Mcknight, Scot, The Sermon on the Mount, The Story of God Bible Commentary, Zondervan, Grand Rapids, MI, 2013, pgs. 11-13.

[28] Additionally, if you want to gain a full understanding of the use of a term in the Bible, the search should also include its usage in the contemporary historical context. A quick guide to word studies can be found here: Additionally, it is always helpful to watch someone who is proficient in something work. We can learn a ton from just simple observation. The Bible Project has done a number of word studies that are very well done, and can provide some insight into how to go about doing a word study:

[29] Pennington, Jonathan, The Sermon on the Mount and Human Flourishing: A Theological Commentary, Baker Academic, Grand Rapids, MI. pg. 76, (citing Patrick Hartin, Spirituality of Perfection, pg. 26).

[30] Ibid, 78.

[31] McKnight, 146.

[32] Pennington, 89.

[33] Allison, 29 (emphasis mine).