New Wine, New Wineskins: Embracing Jesus' New Way

Heartland is invited into an expectant posture for what God is doing—an unfolding newness that cannot be squeezed into old containers. Drawing from Jesus’ encounter with Matthew and the scandal it provoked among religious leaders, a picture emerges: Jesus is the new cloth and the new wine, not a patch on existing systems but the inaugurator of a transformed way of life. The calling of a tax collector, the controversy at Matthew’s house, and the parable about garments and wineskins together indict any attempt to graft Jesus onto hardened structures or rule-bound religiosity. Instead of behavior modification, the gospel announces interior transformation: those in Christ are new creations and must allow their inner “containers” to be softened and reshaped.

The sermon traces how fear of change drives resistance—whether in first-century Pharisees or modern congregations—and shows how clinging to the familiar can obscure the very presence of Christ when he stands among people deemed unworthy. Practical invitations follow: surrender all areas of life so Jesus can remold the heart; pursue becoming rather than merely asking “what’s next”; refuse complacency by continually opening to transformation; and make room for more people to taste the good news. Real change requires daily decisions to follow, not the attempt to staple new life onto old identity.

Illustrations—from wineskins and garments to New Coke—underscore how preservation of an old form can destroy new content. Yet the account closes with hope: Jesus’ first miracle at a wedding served the best wine last, signaling that what he produces is superior to any past comforts. The call is both urgent and generous—open the heart, expand the community, and expect the surprising reach of grace. When the container is pliable, God’s new thing not only fits but overflows in ways that renew individuals, families, and whole communities.

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Key Takeaways

• 1. Jesus brings a fundamentally new way The life Jesus inaugurates cannot be appended to existing religious systems; it reorients identity and practice from the inside out. Trying to graft Jesus onto hardened rituals or moralism risks rupturing both the old form and the new life he offers. The parable of patching garments and wineskins underscores that authentic discipleship requires structures and hearts capable of holding fermenting grace. [46:03]
• 2. Surrender the whole heart daily Transformation is an ongoing, daily surrender rather than a one-time behavioral fix. Offering every corner of life to Christ allows the “container” of the soul to become pliable and receptive to true conversion. This surrender trusts that God’s reshaping produces flourishing, not merely compliance. [54:57]
• 3. Pursue transformation, not just what's next Asking “what’s next” often masks an avoidance of present change; God cares more about who a person becomes than the sequence of events in life. Allowing God to form character now prevents carrying the same inner habits into future seasons. Spiritual growth is formation, not simply relocation. [57:05]
• 4. Make room so everyone belongs The gospel expands the boundaries of community and insists that barriers built to preserve purity often exclude those most in need of grace. A pliable church creates space for people the old systems rejected—sinners, poor, outsiders—and in doing so reflects the breadth of Christ’s invitation. Openness to new people reveals the kingdom’s generosity. [62:51]

Youtube Chapters

• [00:00] - Welcome
• [33:59] - Expectation After 40 Days of Prayer
• [34:58] - Theme: God Is Doing Something New
• [36:17] - Context: Jesus’ Early Ministry
• [36:40] - Calling of Matthew (the Tax Collector)
• [38:57] - Dinner at Matthew’s House
• [39:30] - Pharisees' Critique and Resistance
• [43:11] - Parable: New Cloth and Old Garment
• [44:32] - Parable: New Wine and Old Wineskins
• [46:03] - Jesus as the New Thing
• [54:57] - Call to Complete Surrender
• [57:05] - Pursue Becoming, Not Just Next
• [59:01] - Warning Against Complacency
• [62:51] - Make Room: Gospel for Everyone
• [66:55] - Best Wine: Promise of the New
• [68:03] - Final Invitation and Prayer

Here is a Bible study guide based on the sermon:

Bible Reading

Matthew 9:16-17 (ESV)
> 16 “No one puts a patch of unbleached cloth on an old garment, for the patch will pull away from the garment, and the tear will be made worse. 17 Neither is new wine put into old wineskins. If it is, the wineskins will burst, and the wine will be spilled, and the wineskins will be ruined. But new wine is put into fresh wineskins, and so both are preserved.”

Luke 5:30-32 (ESV)
> 30 The Pharisees and their scribes grumbled at his disciples, saying, “Why do you eat and drink with tax collectors and sinners?” 31 And Jesus answered them, “Those who are well have no need of a physician, but those who are sick. 32 I have not come to call the righteous, but sinners to repentance.”

2 Corinthians 5:17 (ESV)
> 17 Therefore, if anyone is in Christ, he is a new creation. The old has passed away; behold, the new has come.

Observation questions

1. Jesus uses the illustrations of patching an old garment with new cloth and putting new wine into old wineskins. What is the common principle behind why these actions would not work, according to Jesus? [43:11]
2. When Jesus is speaking to the Pharisees and scribes, what is their primary complaint about Jesus’ actions? [42:13]
3. The sermon mentions that Jesus’ first miracle involved wine. What was the reaction of the host at the wedding feast to the wine Jesus provided? [01:07:19]
4. The sermon states, "Therefore anyone who is in Christ is a new creation. The old is gone and the new is here." [53:46] What does this verse suggest about the nature of transformation that happens when someone is in Christ?

Interpretation questions

1. The Pharisees and scribes were experts in the Old Testament law and acted as enforcers. [39:30] How might their rigid adherence to the law have prevented them from recognizing the "new thing" Jesus was doing?
2. Jesus' parable about new wine and old wineskins illustrates that new content requires new containers. [44:32] How does this apply to our lives and our willingness to embrace the newness that Jesus brings?
3. The sermon highlights that "Jesus didn't come to make us better. He didn't come to straighten us out. He came to make us new." [54:07] What is the significant difference between being made "better" and being made "new" in the context of faith?
4. The sermon suggests that "transformation is not a one time thing. Life with Jesus is ongoing transformation." [01:00:34] How does the idea of "new wine" and "fresh wineskins" support the concept of ongoing transformation rather than a single event?

Application questions

1. The sermon emphasizes that Jesus is not a patch job but brings a fundamentally new way of life that reorients identity from the inside out. [46:03] In what areas of your life might you be trying to "patch" Jesus onto your old ways instead of allowing him to create something entirely new?
2. The sermon challenges us to "pursue new, and not just what's next." [57:05] What are some ways you can actively pursue the "new" that God is doing in you right now, rather than just waiting for the next event or season of life?
3. We are encouraged to "refuse complacency by continually opening to transformation." [01:00:09] What is one specific step you can take this week to resist complacency and remain open to God's transforming work in your life?
4. The sermon calls us to "make room so everyone belongs," [01:02:51] recognizing that the gospel expands the boundaries of community. Who is one person in your life or community that you can intentionally make more room for this week, reflecting the breadth of Christ’s invitation?
5. The idea of surrendering our hearts daily to allow them to be "moldable again and pliable again in his hands" [56:19] is presented as the best way to live. What is one area of your life that you find difficult to surrender completely, and what might it look like to offer that area to Jesus daily?
6. The sermon notes that "Jesus’ first miracle had to do with wine... you saved the best till now." [01:06:55] How can remembering that what Jesus offers is superior to any past comforts encourage you to embrace the newness He is bringing into your life, even when it feels challenging?