Gentle Jesus: Friend of Sinners (Matthew 11:16-30)


On August 6, 1930, Supreme Court Judge Joseph Crater vanished on the streets of Manhattan, near Times Square. The dapper 6’ tall and dearly loved 41 year old man’s disappearance launched a massive investigation that captivated not just NY City but the entire nation at the time; earning Judge Crater the title: “the missingnest man in New York.” There was suspicion of foul play, possible kidnapping, murder, even mafia connections, or perhaps suicide. While there were countless theories but no conclusions, the only real evidence investigators knew for certain was that his wife found in her home a cash-stuffed envelope and a letter from her husband that simply read: “I am very weary. Love, Joe.” Those very words guided investigations for many years later, but eventually in 1939, at his wife’s request, Joseph Crater was declared legally dead.

Those despairing words describe many people today, perhaps some of you hearing my voice in person or online. Weariness is more than physical fatigue but mental and emotional exhaustion.

  • 2021 is known as the year of the “Great Resignation,” with around 40% of employees from multiple industries quitting or expected to quit their jobs.[1] That’s millions of workers with employers having acute labor shortages that we all are observing as we enter stores and make purchases with longer and longer waiting for services.  
  • I spoke with a pastor this week who told me this past year has felt so heavy that he has no more to give, and was planning to retire in no less than the next twelve months. Scores of pastors are doing the same, some in our area and others around the country.[2]
  • Speaking to many in our congregation and community, I have heard the weariness of circumstances with doubtful outlook and shrinking hope of change.

Today, I want to remind all that we have an anchor for the soul – the Lord Jesus Christ. I realize this statement brings different perspectives for how one receives this assurance.

  • For many the approach is running. We run and race to fill our life with happiness and meaning. We seek to accomplish many activities and please many people, but all we end up doing is becoming F.I.N.E. people, which stands for: frustrated, insecure, neurotic, empty.
  • The other approach to this anchor hope is not running but resting. While many religions and churches give us long to-do and to-don’t lists, Jesus gives us a done list. He declares everything to be finished and final based on His righteous life that is required of us, and His sacrificial punishment on the cross that we deserve as death. Jesus lived and died for us so we no longer have to run but rest in His presence.

In fact, many/most sermons you hear are about telling us what we should do. But the true and better sermons are those telling us not just what, but who and why. Our next series is based around a book titled: Gentle & Lowly, which helps us get to know the heart of Christ for sinners and sufferers. The author writes, “This book is written for the discouraged, the frustrated, the weary, the disenchanted, the cynical, the empty. Those running on fumes. Those whose Christian lives feel like constantly running up a descending elevator. Those of us who find ourselves thinking: ‘How could I mess up that bad – again?’”[3] This study will help us live in the awareness of God’s affection for us through Christ’s atonement, so that we move beyond just knowing some facts about God, but we genuinely grow to know the person and heart of God.

  • Like a spouse[4] who can introduce their spouse based on their height, eye and hair color, education, job, Myers-Briggs personality profile, the favorite food and hobbies, and those unique (and maybe unpleasant) things they do and sound like when they sleep.

  • But it is harder for the spouse to describe what they see based off a look across the dinner table or a glance across the room. Those reflections only come from years of an ever-deepening relationship, thousands of conversations (and conflicts), and time-ripened assurance to describe not just about them but who they are. It is one thing to describe what a person looks like, and another all together deeper and more profound to describe their heart.

There are many Scripture verses and passages that tell us what God has done and Jesus has accomplished. But there is only one verse in all the Bible that tells us the actual heart of God. Let’s explore this verse together in its context.

EXAMINE       Matthew 11:16-30        2 characteristics about the heart of Christ

Jesus does not play religious games; His heart is holy.

  • Jesus compares the generation to demanding playmates. The religious leaders of the day wanted people to follow their man-made rules, while they did not follow human or divine law.
    • “[This generation is like] children sitting in the marketplaces and calling to their playmates, ‘We played the flute for you and you did not dance; we sang a dirge and you did not mourn.’ For John came neither eating nor drinking, and they say, ‘He has a demon.’ The Son of Man came eating and drinking, and they say, ‘Look at him! A glutton and drunkard, a friend of tax collectors and sinners!’ Yet wisdom is justified by her deeds.’” (Mt 11:16-19)

    • “But woe to you, scribes and Pharisees, hypocrites! For you shut the kingdom of heaven in people’s faces. For you neither enter yourselves nor allow those who would enter to go in. Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful but within are full of dead bones and all uncleanness. So you also outwardly appear righteous to others, but within you are full of hypocrisy and lawlessness.” (Mt 23:13, 27-28)
  • Likewise, Jesus rebukes stubborn pride.
    • “Jesus denounced the cities where most of his mighty works had been done, because they did not repent. Woe to you Chorazin! Woe to you Bethsaida! For if the mighty works done in you had been done in Tyre and Sidon, they would have repented long ago… but I tell you it will be more bearable on the day of judgment for Tyre and Sidon than for you. And you Capernaum, will you be exalted to heaven? [No.] You will be brought down to Hades. For if the mighty works done in you had been done in Sodom, it would have remained until this day. But I tell you that it will be more tolerable on the day of judgment for the land of Sodom than for you.” (Mt 11:20-24)
      • Chorazin was in Galilee, where Jesus was known as a Galilean (Mt. 26:69). It was in this region Jesus preached the Sermon on the Mount and did many healing miracles.[5]  
      • Bethsaida was another city in Galilee. This was the home of some of the disciples (Jn 1:44; 12:21). It was also near where Jesus fed the 5K (Lk 9:10) and healed a blind man (Mk 8:22).[6]
      • Capernaum was a base of operations for much of Jesus’ ministry (Mk 1:21; 2:1, 24; 7:5; Mt 9:1; Jn 6:15).[7]
      • Tyre, Sidon, and Sodom were paradigms of Israel’s enemies and evil practices (Isa 23; Ez 26-28; Am 1:9-10; Gen 18-19).[8] Jesus claims these towns would have less judgment than cities who physically saw God’s Messiah and stubbornly rejected Him.  
      • God conceals spiritual truth from the earthly wise and reveals grace to the humble (Mt 11:25-27).

Overall, Jesus has a holy rebuke for those who pridefully claim to be religious but are not; and Jesus has open invitation to contrite sinners and confessed strugglers. Ortlund says, “Jesus is not harsh, trigger happy, reactionary, easily exasperated. He is the most understanding person in the universe. The posture most natural to him is not a pointed finger but open arms.”[9] So, the heart of Jesus is holy. He does not play religious games but invites people to genuine relationship.

  • Unclutter your religious views by reflecting on the life of Jesus. Read a Gospel. See if your perspectives about life and faith measure to the teaching of Jesus.

  • If you are a Christian, you stop religious games by moving beyond Sunday to the everyday. While Sunday gatherings are important, God’s mission for you is more than an event but a daily experience. He has plans for you and through you to make a difference and multiply disciples of Jesus.

Jesus invites us to radical discipleship; His heart is humble.

Jesus says, Come to me, all who labor and are heavy laden, and I will give you rest. Take my yoke upon you, and learn from me, for I am gentle and lowly in heart, and you will find rest for your souls. For my yoke is easy, and my burden is light.” (Matthew 11:28-30)

Jesus reveals the rare blend of holiness and humility, power yet compassion. He extends an open invitation for all to come to him. Jesus offers relationship before rules. Jesus criticized His adversaries, the Pharisees teaching that “tied up heavy burdens, hard to bear, and lay them on people’s shoulders, but they themselves are not willing to move them with their finger. They do all their deeds to be seen by others. For they make their phylacteries broad and their fringes long, and they love the place of honor at feasts and the best seats in the synagogues and greetings in the marketplaces and being called rabbi by others.” (Matthew 23:4-7).

In contrast, Jesus’ teachings were “easy” (χρηστός = pleasant, gracious). Jesus notes that those who attempt life apart from Him labor (κοπιάω: copious work, toil and fatigue; tense: present active action) and heavy laden (φορτίζω: load up, overburden; tense: passive action applied to person) with Jesus’ rest. The tense of the first labor is an internal weariness caused by human pursuit of accomplishment and achievement, whereas the second heavy-ladenness is external weight caused by the demands and commands placed by others.

Jesus did not come to bring a new religion but Himself. Ortlund writes, “The point in saying that Jesus is lowly is that he is accessible. For all his resplendent glory and dazzling holiness, his supreme uniqueness and otherness, no one in human history has ever been more approachable than Jesus Christ.”[10] The only prerequisite for coming to Jesus is being heavy laden and burdened. Amazingly, the same sin that disqualifies you from holiness is what qualifies you for the free grace of the Savior. Jesus doesn’t ask us how we became burdened; which specific sins we have – as if certain one’s are too difficult to forgive; or how long we’ve struggled. He just invites us to come because He is gentle and gracious.

When we think of being heavy-laden & burdened:

  • picture an animal or ship loaded down & unable to travel.
  • picture one attempting to navigate the stress and struggles of the last two years (or any years really) all alone.  
  • picture a person in a hospital or hospice room alone.
  • picture most moms… especially single moms!
  • picture your neighbor who doesn’t know the forgiving grace and confident hope of Jesus Christ.   

While Jesus’ heart is humble and gentle, He is not a pushover. He calls us to radical discipleship with yoke imagery. When we think of Jesus’ yoke:

  • Some picture Jesus’ yoke as enslavement.
  • Would a person drowning who was thrown a raft on rescue rope view it as oppressive and judgmental?
  • Instead, we should understand the yoke imagery not as enslaving but as empowering. The power of being yoked to Jesus and following His principles the difference between tow capacity of a turtle and a Toyota. Spiritual salvation and physical rest are not freedom from responsibility but devotion to the right priorities. We must be yoked to the right object, or we will lack the power and effectiveness for life.

The promised reward for following Jesus is rest for our soul. It’s not always comfort to our feelings, decline of troubles, or ease for our faith. Instead of escape from challenges, Jesus gives us restful peace to endure in them. Christian salvation is not just rest after death but refuge during life. In Christ, there is an eternal peace to experience that passes all earthly understanding.

  • Radical discipleship includes three steps
  • Meeting the biblical Jesus.
    • Be careful of meeting Secular Jesus, or Religious Jesus, or even Chosen Jesus. These are all fine to understand but there is only one Jesus that is worthy of uniting your faith and following.
  • Maturing in biblical depth.
    • Maturity is not necessarily about length of church attendance as much as it is Christian obedience.
      • Mt 19 Rich Ruler followed moral principles but lacked complete obedience to Jesus.
      • James 1:22 Do not merely hear the word, do it, unless you deceive yourself.  
  • Multiplying
    • Making disciples is the heart of Jesus (Mt 28:19-20)
    • “If you say you are following Jesus but are not helping others to know and follow Jesus then I don’t know what you mean when you say ‘I follow Jesus.’” (Mark Dever)


Remember when you were youthful in love. You would analyze in your own head, question others, and observe various scenarios if the person of your eye had return heart for you. It was such a guessing game.

When it comes to God, we do not have to guess about His heart for us. God’s heart is obvious and tangible when we look at the cross of Jesus.

Romans 5:8 “But God demonstrates his own love for us in this: While we were still sinners, Christ died for us.”

1 John 4:18-19 “There is no fear in love. But perfect love drives out fear, because fear has to do with punishment.  The one who fears is not made perfect in love.  We love because He first loved us.”

Psalm 103:10-12   “He does not deal with us according to our sins, nor repay us according to our iniquities. For  as high as the heavens are above the earth, so great is his steadfast love toward those who fear him; as far as the east is from the west, so far does he remove our transgressions from us.”  

Thomas Goodwin: “If you knew his heart, you would.”



[3] Dane Ortlund, Gentle And Lowly, p.13.

[4] Illustration adated from Ortulnd, p.16.

[5] Galilee. (2003). In C. Brand, C. Draper, A. England, S. Bond, E. R. Clendenen, & T. C. Butler (Eds.), Holman Illustrated Bible Dictionary (p. 617). Holman Bible Publishers.

[6] Vermillion, W. H. (2003). Bethsaida. In C. Brand, C. Draper, A. England, S. Bond, E. R. Clendenen, & T. C. Butler (Eds.), Holman Illustrated Bible Dictionary (p. 196). Holman Bible Publishers.

[7] Knight, G. W. (2003). Capernaum. In C. Brand, C. Draper, A. England, S. Bond, E. R. Clendenen, & T. C. Butler (Eds.), Holman Illustrated Bible Dictionary (p. 265). Holman Bible Publishers.

[8] Blomberg, C. (1992). Matthew (Vol. 22, p. 191). Broadman & Holman Publishers.

[9] Ortlund, p.19.

[10] Ortlund, p.20.

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