Blessed | Part 1: The Blessed Life | Pastor Jacob Sheriff

Message Date: May 17, 2026
Bible

Blessed, Part 1: The Blessed Life

Victory Life Church — Sunday, May 17, 2026

Link to a downloadable PDF:
2026-05-17 – Blessed, Part 1 (Full Notes)

Scripture Reading

Matthew 5:1–12 (ESV)1 Seeing the crowds, he went up on the mountain, and when he sat down, his disciples came to him. 2 And he opened his mouth and taught them, saying: 3 “Blessed are the poor in spirit, for theirs is the kingdom of heaven. 4 “Blessed are those who mourn, for they shall be comforted. 5 “Blessed are the meek, for they shall inherit the earth. 6 “Blessed are those who hunger and thirst for righteousness, for they shall be satisfied. 7 “Blessed are the merciful, for they shall receive mercy. 8 “Blessed are the pure in heart, for they shall see God. 9 “Blessed are the peacemakers, for they shall be called sons of God. 10 “Blessed are those who are persecuted for righteousness’ sake, for theirs is the kingdom of heaven. 11 “Blessed are you when others revile you and persecute you and utter all kinds of evil against you falsely on my account. 12 Rejoice and be glad, for your reward is great in heaven, for so they persecuted the prophets who were before you.

Introduction

What does it mean to be “blessed”?

Think about someone that you think is “blessed.” When we think of someone who is “blessed,” what are we seeing that makes us think that? What about their life indicates that they are well off? What makes someone “blessed” or not? What would make you think someone has “the good life” or is “well off”?

Said another way, what makes you think someone is not blessed? What are you seeing in someone’s life that makes you think they are not well off, not living the good life?

Lottery Winner: William “Bud” Post III

William Post III, nicknamed “Bud,” had had a run of bad luck in his life. When he was eight years old, his mother died. His father, unable or unwilling to raise him, later sent Bud to an orphanage. When he got out, he struggled to adapt to society and earn a decent living. He spent most of his adult life puttering through various jobs, like spray-painting pipelines or being a cook and truck driver for circuses and carnivals. He had never owned a home or a car. Money had been hard to come by in Bud’s life. Things had gotten so bad that he had even served a twenty-eight-day jail sentence for writing too many bad checks. Then one day, Bud decided to buy a lottery ticket. At the time, he was on disability and had a grand total of $2.46 in his bank account. He had nothing to lose and over sixteen million dollars to win… and it happened! William “Bud” Post III won $16.2 million in the Pennsylvania lottery in 1988. It would make sense to think that Bud was now “blessed,” or that luck was smiling on him.

Jesus begins his famous “Sermon on the Mount” with the word “blessed.” When we think about what it means to be blessed in today’s world or with our cultural values, we may craft a set of statements like this:

Blessed are the rich, for they can buy whatever they want.

Blessed are the powerful, for they can get whatever they want.

Blessed are the famous, for everyone knows their name.

Blessed are the successful, for they are winning at life.

As much as these may make sense to us, are these the people Jesus describes as blessed? Is the good life defined as these things: wealth, power, fame, and success?

The Kingdom of God — what, and for whom?

First, we need to see a little bit of the backstory to the Sermon on the Mount. Matthew begins telling the story of Jesus’ ministry, beginning with a summary statement:

Matthew 4:17 (ESV)17 From that time Jesus began to preach, saying, “Repent, for the kingdom of heaven is at hand.”

This is what Jesus’s ministry was all about: announcing and enacting the Kingdom of God. What does this mean, though? “Kingdom” (Greek: basileia) refers to the domain over which a king rules. But beyond the idea of this being simply a noun, it also means “reign”, which is the exercise of royal power, more akin to an active verb. “The Reign of God” can be defined as “the range of God’s effective will.” The sphere where God’s will is done “on earth as it is in heaven.”

The Kingdom or Reign of God can be defined as “the range of God’s effective will.”

In history, when you hear of “the reign of the Pharaohs, or Alexander the Great, or Henry VIII”, you would understand it to refer to a people and a place, but also to the order imposed upon a people and place by that monarch. This statement would refer to the people and place of Egypt, or Greece, or England who live under the order imposed upon by those kings.

“The kingdom is the King’s power over the King’s people in the King’s place.”

The Kingdom of God is the range of His effective will, the reign of God; it is God in action. It’s referring to His ordering and directing of the world, it is the realm and reality in which the way things are directly under His will, and His people who are yielded and partnering with His action. Simply put, “the kingdom of heaven” is God’s domain, His rule and reign. Jesus is announcing that God’s domain is invading mankind’s domain, His rule is taking over humanity’s rule, and it is happening in the work of Jesus Christ.

“When [Israel] longed for the kingdom of God, they were not thinking about how to secure themselves a place in heaven after they died. The phrase ‘kingdom of heaven’ … does not refer to a place, called ‘heaven,’ where God’s people will go after death. It refers to the rule of heaven, that is, of God, being brought to bear in the present world… Jesus’ contemporaries knew that the creator God intended to bring justice and peace to his world here and now.” ~ N. T. Wright

With this framework in mind, Jesus begins His introductory Sermon of what it is like for the Kingdom of God to advance in the world, His reign announced and enacted in God’s people in this world. This is a sermon delivered to his disciples, not just to a generic crowd.

Matthew 5:1–2 (ESV)1 Seeing the crowds, he went up on the mountain, and when he sat down, his disciples came to him. 2 And he opened his mouth and taught them…

The people Jesus is delivering this sermon to are a crowd of ordinary, unlikely people. Jesus, full of compassion, sat on a mountain and spoke to them: to the unlucky, to the outcast and insignificant, to the overlooked and undervalued.

The people Jesus is delivering this sermon to are a crowd of ordinary, unlikely people.

These are not the powerful, the wealthy, or the religious elite. These are people who are not at the top of any list made about who is well off in the world. These are people whom the powerbrokers of the world would consider outsiders and insignificant. This is a crowd of people whom the religious would consider “beneath” them, or “outsiders” of whom God considers the qualified for His blessing! In other words, every day, unimportant people like us. And the word he confers upon them is “blessed.”

What Are the Beatitudes?

Jesus introduces the Sermon on the Mount with a series of blessings known as the Beatitudes. How do we understand what a “beatitude” is? The name “beatitude” comes from the Latin beatitudo/beatus, because the first word of each statement in the Latin Vulgate is beati, which translates the Greek word makarios. Why would He start here? Because, before anything else, Jesus wants us to understand the foundation of His kingdom. The Beatitudes show us that Jesus’ kingdom is built on the bedrock of grace and blessing.

Jesus dares to claim that the oppressed and the depressed are actually blessed.

“Blessed”

When we hear this word, “blessed,” we have all sorts of baggage and assumptions about this word. The word Jesus used to introduce the people for whom the Kingdom of God is for is the Greek word makarios. Most of our English translations use this word; it is not an inaccurate translation. However, that word is littered with religious and cultural baggage. In religious circles, it is a broad and bland adjective to describe a feeling of things being good in life right at that moment: “I’m blessed and highly favored, thank you, Jesus, hallelujah, amen. Praise God.” Some super-spiritual people use it as a faith band-aid for problematic circumstances: “I’m blessed,” gritting their teeth and furrowing their brow, despite life falling apart. In cultural settings, it is a catch-all phrase to describe how good life is: #blessedlife, tagged onto vacation pictures or snapshots of a brand new possession, or a quaint moment with friends or family. All of this may offer hints about what that word means, but our images of “blessed” may be a far cry from the way Jesus describes people who are actually blessed.

Makarios is not a wish or prayer, as in “O Lord, please bless me…”, but a declaration recognizing an existing state. Makarios is difficult to fully capture in translation because “there is no good, single [word] in English that communicates the complexity, beauty and nuance” of this word. It can mean simply “fortunate” or “happy,” or even “blissful” or “flourishing.” However, these can also carry too much baggage and misunderstandings.

“Blessed” — makarios — “fortunate, happy, blissful, flourishing.”

Scholar Scot McKnight observes, “on this one word the entire passage stands, and from this one word the whole list hangs. Get this word right, the rest falls into place; get it wrong and the whole thing falls apart.”

In secular Greek literature, makarios is used to describe the blissful state of the gods. It is not an inherently religious word. The Greek word that is more like our words “blessed” or “blessing” is eulogia. Eulogia is often used to invoke or invite God’s blessing and to bless God. (The Hebrew word for this is “bārûk.”) That word was available to Jesus, but He chose makarios instead.

In the Septuagint, the Greek translation of the Hebrew Old Testament (the version of the Scriptures many in Jesus’ day would have used), makarios is the word most often used to translate the Hebrew asar (awshway). But asar is not the word for a “God-blessed” person, thing, or action. In fact, it is rarely used of God blessing anything or anyone.

Asar is used of “someone who is to be congratulated, someone whose place in life is an enviable one,” someone who is “well off.” It is simply “happy, favored, prosperous” and has the connotation of one whose paths are straight. That would be a way of saying of someone for whom things always unfold neatly and nicely.

Psalm 1:1–2 (ESV)1 Blessed is the man who walks not in the counsel of the wicked, nor stands in the way of sinners, nor sits in the seat of scoffers; 2 but his delight is in the law of the Lord, and on his law he meditates day and night.

Asar, specifically in the Psalms, is a way of referring to a flourishing life, “to true happiness and flourishing within the gracious covenant God has given.” This kind of life is a promise that comes through faithfulness to the Lord, which ironically is the very thing that the wicked promise apart from the Lord.

“Thus, when the Psalms speak of the [asar state] of the one who meditates on Torah, …this is simultaneously a claim that this God-oriented person is in a state of flourishing precisely because he or she is experiencing the most direct means of grace that God has ordained to effect favor upon his people—…knowing God [personally].” ~ Jonathan Pennington

Even though asar has the implication that God is the true source or reason for the person’s blessedness, it is not inherently a religious word. It’s a marketplace word, used to simply say that a person is fortunate, that he “has it good,” or is “well off.”

If we were to use a similar word today for makarios, an appropriate word would be “lucky.” Now hear me out. I don’t mean “lucky” as in the result of randomness. Not “lucky” as in the reward for properly acknowledging a superstition or a charm. It is neither the product of erratic chance nor the result of currying favor with some capricious god. It is simply lucky as we use it conversationally: “You lucky dog, you get to take a vacation next week!” Or, “Lucky you! You just got a promotion in the middle of a recession!”

Makarios, as one New Testament commentator suggested, is akin to the Aussie slang “Good on ya, mate,” which is rather like the American, “Good for you!” Which is like saying, “Lucky you!” Jesus, in these Beatitudes, is forcing us to rethink who is really “blessed” and “well off” in the world. The people we consider “lucky” and “blessed” may not be as we think.

William “Bud” Post III — “the rest of the story.”

Bud Post chose to get his lottery winnings in twenty-six annual payments of roughly half a million dollars. Within two weeks of collecting his first installment, he had spent over three hundred thousand dollars of it. Three months later, he was half a million dollars in debt—thanks to (among other things) a restaurant in Florida he had leased for his sister and brother, a used-car lot complete with a fleet of cars he had bought for another brother, and a twin-engine plane he had bought for himself even though he didn’t have a pilot’s license. A year later, debt wasn’t his only problem. He became estranged from his siblings, and a county court ordered him to stay away from his sixth wife after he allegedly fired a rifle at her vehicle. Bud Post was Dale Carnegie in reverse: a millionaire losing friends and alienating people while accruing a mountain of debt. When his former landlady sued him for a portion of the winnings to pay off old debts, Bud was finished. The judge ruled that she was entitled to a third of his lottery winnings, and when Bud couldn’t pay it, the judge ordered that all further payments of his winnings be frozen until the dispute was resolved. Desperate for cash, Bud sold his Pennsylvania mansion in 1996 for a miserable sixty-five thousand dollars and auctioned off the remaining payments of his winnings. With a little over two and a half million dollars remaining, Bud hoped that people would finally leave him alone. But the person who created the most trouble was the one he could never escape: himself. He squandered it on two homes, a truck, three cars, two Harleys, a couple of big-screen TVs, a boat, a camper, and a few computers. By 1998, ten years after winning $16.2 million, Bud Post was once again living on disability payments. Bud lamented, “I was much happier when I was broke.” William “Bud” Post III died at age sixty-six of respiratory failure, broke and alone.

This story is a tragic tale that should disrupt our assumptions. Was he lucky or not? Is this kind of life what we call blessed? This should make us pay close attention to Jesus’ word choice of makarios. He ironically calls the ordinary, unspectacular people before Him “blessed.” Jesus is looking at these ordinary, unspectacular people and exclaims, “Lucky you!” He might as well have said, “Lucky are the unlucky!”

Jesus took an inherently nonreligious word, a word from normal everyday conversations, and filled it with divine implications. It turns out the ones we ought to call lucky are the ones God is blessing with the arrival of His kingdom. In doing this, Jesus redefined who the blessed ones are. They are not the ones culture lauds as successful, not the ones we secretly aspire to be. He turned our appraisal of the good life on its head. There is a great reversal coming; indeed, it has already begun. And the ones who are receiving and participating in the kingdom of God are the ones who are truly lucky, deeply blessed.

Important Note

“While the Beatitudes speak of God’s favor or blessing, this is not to be understood in a legalistic way of us earning God’s favor but rather of God working these same things in us by grace or by the Spirit.” The Beatitudes are not to be understood as “conditional,” meaning these are not pre-requisite conditions you have to be in to receive God’s blessing; neither are they merits to earn His grace. These are not ideals we are called to aspire to or “entrance requirements” to get into God’s kingdom. They are simply revealing Jesus’ foundation of grace, the kinds of people who are ready to receive the grace Jesus and His Kingdom offer. These are radical reversals of the world’s values.

“The religious system of his day left the multitudes out, but Jesus welcomed them all into his kingdom. Anyone could come as well as any other. They still can. That is the gospel of the Beatitudes.” ~ Dallas Willard

Each of Jesus’ Beatitudes contains an explicit pronouncement of invitation to those seemingly unworthy of the kingdom, but each also contains an implicit pronouncement of condemnation on those who think themselves to be worthy but are not.

Conclusion

Though this may sound technical, it’s very important to understand properly what Jesus means by “blessed”. He is not saying that one must force oneself into these positions to earn God’s favor. He is not saying that these are the exclusive ethics of how one must show up in the world and aspire to become. He is saying that these states are perfectly suited to receive and walk in God’s favor. Or said another way, these states of being are commonly excluded from a life of flourishing according to the world’s standards and aspirations, yet these are the states of being perfectly suited for God’s kingdom reign and the blessing that flows from life with God. These truly are the good life because they are ways of being in the world that are ready for and dependent on God’s work.

Jesus doesn’t define blessing in terms of wealth, possessions, or power. Instead, He shows us that the kingdom of God is built on a bedrock of blessing, where the least are most, the last are first, and the lost are found. Being blessed by God doesn’t come from accumulating wealth, achieving success, or acquiring fame. Being blessed by God comes from knowing and following Jesus.

If Jesus were sitting across the table from you and said to you that you are “blessed,” that He counts you as lucky, what would you think? “That’s crazy! No, I’m not,” you might insist. “I’m ordinary, unspectacular. And besides, I’m too messed up; I’ve made too many mistakes. I’m the person on the fringes, the margins, the outskirts. I’m not admired or applauded, respected or rewarded. I’m just … me. And whatever that is, it’s not “blessed.” And yet, you are perfectly suited for the good life because being blessed is not primarily about a change in circumstances but about an awareness of your need for a relationship with Jesus.

Conclusion: It’s all about a personal relationship with Jesus.