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			New Wine in Old 
			Wineskins 
			Matthew 9:17; Mark 2:22; Luke 5:37–38 
			
			Introduction 
			Open the Gospels and you will find Jesus in the middle of a 
			conversation about fasting at a banquet in Levi’s house. The Lord 
			has just called a tax collector to follow Him, and the table is full 
			of people whom the religious elite would never invite. Into that 
			scene Jesus tells a picture-story about wine and wineskins. With a 
			few sentences He shows why His kingdom cannot be contained inside 
			old, rigid containers. He is ushering in the promised new covenant, 
			and it requires new, Spirit-softened hearts. 
			
			Setting the 
			Parable 
			Matthew, Mark, and Luke place this teaching alongside the question, 
			“Why do John’s disciples and the Pharisees fast, but Your disciples 
			do not?” (cf. Matthew 9:14; Mark 2:18; Luke 5:33). Jesus answers 
			with three images: a wedding feast with the bridegroom present, a 
			new patch on an old garment, and new wine in old wineskins. The 
			images build a single truth: the arrival of the Messiah brings a new 
			era, and the forms that once fit will tear and burst if we try to 
			force His life into them. 
			
			What Wine 
			and Wineskins Meant to Jesus’ Hearers 
			In the first century, new wine was poured into fresh goatskin 
			bottles. As the wine fermented, it expanded. A fresh skins’ fibers 
			could stretch and flex; a brittle, age-stiffened skin would crack 
			under that same pressure. Everyone listening knew the outcome. New 
			wine demands a container with life and give. Jesus is saying: “The 
			life I bring will expand; it cannot be squeezed into lifeless 
			forms.” 
			
			The Lord’s 
			Point 
			Jesus is not tinkering at the edges of religion. He is fulfilling 
			the prophets—bringing the new covenant written on hearts (Jeremiah 
			31:31–34), giving a new heart and a new spirit (Ezekiel 36:26), and 
			serving as Mediator of a better covenant (Hebrews 8:6–13). The “new 
			wine” is His gospel, His Spirit, His kingdom life. The “wineskins” 
			are the structures and dispositions that carry that life—hearts, 
			habits, communities, and expectations. When people try to pour 
			Jesus’ life into unchanged hearts or use His message to prop up 
			empty tradition, the result is loss on both sides: the wineskin 
			bursts and the wine spills. God intends preservation and 
			increase—wine preserved and wineskins kept (Luke 5:38). 
			
			Why Many 
			Prefer the Old 
			Luke adds a line that feels painfully honest: “No one after drinking 
			old wine desires new, for he says, ‘The old is good’” (Luke 5:39). 
			Familiar paths feel safe. Old habits, inherited traditions, and 
			long-held assumptions quiet the conscience because they require no 
			change. Yet the kingdom presses forward. The Bridegroom is present. 
			The Spirit moves. Those who cling to the familiar can miss the feast 
			that is set before them. 
			
			Marks of a 
			New-Wineskin Heart 
			A heart ready for Jesus’ new wine shows certain graces. It stays 
			tender and teachable under Scripture, eager to understand and obey 
			all that Christ commands (Ephesians 5:17; Matthew 28:20). It 
			welcomes the Spirit’s transforming work—putting off the old self and 
			putting on the new (Ephesians 4:22–24), serving in the new way of 
			the Spirit (Romans 7:6), and walking as a new creation (2 
			Corinthians 5:17). It practices joyful discipline—fasting, prayer, 
			generosity—without turning practices into barriers for others (Mark 
			2:18–22; Colossians 2:16–17). It shows holy flexibility in methods 
			while holding the message with both hands (1 Corinthians 9:22; 
			Colossians 3:17). It prizes grace over reputation, because Jesus 
			keeps calling unexpected people to the table (Matthew 9:9–13). 
			
			
			Congregational Implications 
			Churches can become brittle. Schedules, styles, and customs slowly 
			harden until the smallest change feels like a threat. The gospel 
			continues to ferment—saving sinners, sanctifying saints, pushing us 
			into prayerful risk for souls. When a congregation keeps the message 
			pure and lets the forms remain supple, the wine is preserved and the 
			skin endures. When forms are elevated above Christ’s mission, the 
			pressure builds. The Lord is kind to warn us. He invites every 
			congregation to be a living vessel for His living word. 
			
			Personal 
			Decisions 
			Many try to stitch a few Christian practices onto an old life: a 
			Sunday hour, a verse on the wall, a habit or two. The Lord calls for 
			more—repentance, baptism into His death and resurrection, and daily 
			surrender to His reign (Acts 2:38; Romans 6:3–4). He pours new wine 
			when we bring Him a yielded heart. If your soul has grown stiff with 
			self-reliance, tradition for tradition’s sake, or fear of change, 
			ask God to soften you. He delights to do it. 
			
			Conclusion 
			At Levi’s table Jesus announced that the long-awaited day had 
			arrived. He still speaks: the King is here; the kingdom is at hand. 
			He gives new wine. Offer Him a heart that can receive it—fresh, 
			yielded, and ready to stretch—and watch His life expand through you. 
			
			Exhaustive 
			Sermon Outline 
			
				- 
				
Title: New 
				Wine in Old Wineskins (Matthew 9:17; Mark 2:22; Luke 5:37–38)  
				- 
				
Introduction 
				 
				- 
				
Setting of 
				the parable 
				 
				- 
				
				First-century picture explained 
				 
				- 
				
The 
				theological center 
					- 
					
New 
					covenant promised and inaugurated (Jer 31:31–34; Ezek 36:26; 
					Heb 8)  
					- 
					
					Gospel/Spirit/kingdom life as “new wine”; hearts and habits 
					as “wineskins”  
					- 
					
God aims 
					for preservation and growth—wine kept, skins kept (Luke 
					5:38)  
				 
				 
				- 
				
Why the old 
				feels safer (Luke 5:39) 
				 
				- 
				
Marks of a 
				new-wineskin heart 
					- 
					
					Teachable under Scripture (Eph 5:17)  
					- 
					
					Transformed by the Spirit (Rom 7:6; 2 Cor 5:17; Eph 4:22–24)  
					- 
					
					Disciplined without weaponizing traditions (Col 2:16–17; 
					Mark 2:18–22)  
					- 
					
Flexible 
					methods, fixed message (1 Cor 9:22; Col 3:17)  
					- 
					
Grace 
					for unexpected guests (Matt 9:9–13)  
				 
				 
				- 
				
				Congregational implications 
				 
				- 
				
Personal 
				decisions 
				 
				- 
				
Conclusion 
				 
			 
			
			Call to 
			Action 
			Bring your heart to God and ask Him to make it new—soft, teachable, 
			and ready for the life of Christ. If you need to obey the gospel, 
			repent and be baptized into Christ today. If you have grown rigid, 
			confess it, seek renewal in the Spirit, and re-enter the Lord’s 
			mission with joy. 
			
			Scripture 
			Reference List 
			
				- 
				
Matthew 
				9:14–17; Mark 2:18–22; Luke 5:33–39 — Context and wording of the 
				parable; wedding, patch, wineskins; the added insight that many 
				prefer the old  
				- 
				
Jeremiah 
				31:31–34 — Promise of a new covenant written on hearts; 
				background for Jesus’ “new wine”  
				- 
				
Ezekiel 
				36:26 — Promise of a new heart and new spirit; the inner change 
				that can carry the gospel’s life  
				- 
				
Hebrews 
				8:6–13 — Christ mediates a better covenant; the old becomes 
				obsolete as the new arrives  
				- 
				
Ephesians 
				5:17 — Call to understand the Lord’s will; marks of a teachable 
				heart  
				- 
				
Romans 7:6 — 
				Serving in the new way of the Spirit; life that expands from 
				within  
				- 
				
2 
				Corinthians 5:17 — New creation language; the person who can 
				carry new wine  
				- 
				
Ephesians 
				4:22–24 — Putting off the old self and putting on the new; 
				practical renewal  
				- 
				
Colossians 
				2:16–17 — Shadows and substance; practices must not eclipse 
				Christ  
				- 
				
1 
				Corinthians 9:22 — Holy flexibility to win souls; methods that 
				stay supple  
				- 
				
Colossians 
				3:17 — Do all in the name of the Lord; Christ’s authority shapes 
				our forms  
				- 
				
Matthew 
				9:9–13 — Jesus calls Levi and eats with sinners; grace at the 
				table of the King  
				- 
				
Acts 2:38 — 
				Repentance and baptism; entering the life Christ gives  
				- 
				
Romans 6:3–4 
				— Burial and resurrection with Christ in baptism; walking in 
				newness of life  
			 
			
			Prepared by David Hersey of the church of Christ at 
			Granby, MO  |