The Parable of the Two Sons
			
			Introduction 
			In the final week of His ministry, Jesus’ authority was challenged 
			in the temple. The chief priests, scribes, and elders questioned His 
			right to teach and act (Mark 11:27–33; Matthew 21:23–27). Jesus 
			exposed their evasion by asking about the source of John’s baptism. 
			Their refusal to answer revealed hearts that prized position over 
			truth. On the heels of that exchange, Jesus told the Parable of the 
			Two Sons (Matthew 21:28–32). The story draws a clear line between 
			saying and doing, between outward show and obedient repentance, and 
			it explains why humble sinners entered the kingdom ahead of 
			religious leaders. 
			
			Context: 
			Authority Questioned, Hearts Exposed 
			The leaders demanded, “By what authority are You doing these 
			things?” Jesus asked them about John: was his baptism from heaven or 
			from men? They would not commit because truth would condemn their 
			refusal to repent. That moment sets the framework for the parable. 
			John came in the way of righteousness, calling Israel to repentance 
			and preparation for the Messiah (Malachi 3:1; Matthew 3:1–3). Many 
			common people received that call; many leaders resisted it (Luke 
			7:29–30). 
			
			The Parable 
			Told (Matthew 21:28–30) 
			A father said to the first son, “Go work today in my vineyard.” He 
			said, “I will not,” but later regretted it and went. The father said 
			the same to the second son. He answered, “I go, sir,” yet never 
			went. Jesus then asked, “Which of the two did the will of his 
			father?” The answer is obvious: the first son. Repentant obedience 
			fulfills the father’s will. 
			
			Who Are the 
			Two Sons? 
			Jesus applies the parable to His audience. Tax collectors and 
			harlots mirror the first son. Their early lives said “no” to God; 
			yet John’s preaching pierced their hearts, and repentance led them 
			into faithful action. The chief priests and elders mirror the second 
			son. Their words sounded respectful, their robes looked devout, and 
			their traditions carried weight, yet they refused John’s call and 
			rejected the Messiah standing before them (Matthew 21:31–32). Jesus’ 
			verdict is sober: those once far off were entering the kingdom ahead 
			of those who styled themselves as guides. 
			
			The 
			Message: Repentance That Works 
			God’s will is not performed by polite speech or inherited status. 
			The Father seeks people who turn and obey. Scripture ties repentance 
			to doing: “Bring forth fruits worthy of repentance” (Luke 3:8). 
			James summarizes it simply: “Be doers of the word, and not hearers 
			only” (James 1:22). When sorrow leads to a changed mind and that 
			changed mind leads to changed behavior, the vineyard gains workers 
			and the Father’s will advances (2 Corinthians 7:10–11). 
			
			Warnings 
			for Religious People 
			Religious visibility can hide spiritual barrenness. Public roles, 
			correct labels, or accurate talk can mask an unyielded will. Jesus 
			later denounced play-acting religion that polished the outside while 
			leaving the heart untouched (Matthew 23:25–28). The parable presses 
			a gracious warning: examine what you actually do with what you know. 
			The Father’s call still sounds: “Go work today in my vineyard.” 
			
			Hope for 
			Penitent Sinners 
			The first son offers strong encouragement. A past filled with 
			refusal does not decide the future. God welcomes those who regret, 
			turn, and go to the vineyard. The doorway into the kingdom stands 
			open to every heart that receives the word and obeys it (Matthew 
			21:31; Acts 2:37–41). Grace meets honesty, and honest repentance 
			becomes obedient service. 
			The Parable of 
			the Two Sons Sermon Outline
			
			
			Call to 
			Action 
			The Father still says, “Go work today in My vineyard.” If your past 
			answer has been “no,” take courage and go now. Regret can become 
			action. If your mouth has said “yes” while your feet stayed still, 
			let today mark a faithful start. Receive the word, repent where 
			needed, and do the Father’s will in the vineyard of your home, 
			congregation, workplace, and community. 
			
			Key 
			Takeaways 
			
				- 
				
				
				Authority Issue: Jesus’ question 
				about John exposes hearts (Mark 11:27–33; Matthew 21:23–27).  
				- 
				
				
				Parable’s Point: Doing the 
				Father’s will identifies true sons (Matthew 21:28–31).  
				- 
				
				Two 
				Paths: Empty assent with no 
				obedience, or repentance that works (Matthew 21:30–32; James 
				1:22).  
				- 
				
				Open 
				Door: Penitent sinners enter the 
				kingdom ahead of pretenders (Matthew 21:31–32; Luke 7:29–30).  
				- 
				
				
				Immediate Duty: “Go work today in 
				My vineyard”—obedience cannot wait (Matthew 21:28; Colossians 
				3:17).  
			 
			
			Scripture 
			Reference List 
			
				- 
				
Matthew 
				21:23–32 — Authority challenged; Parable of the Two Sons  
				- 
				
Mark 
				11:27–33 — Parallel authority exchange  
				- 
				
Luke 7:29–30 
				— Response to John’s baptism  
				- 
				
Malachi 3:1; 
				Matthew 3:1–3 — John prepares the way  
				- 
				
Luke 3:8 — 
				Fruits worthy of repentance  
				- 
				
James 1:22 — 
				Doers of the word  
				- 
				
Romans 2:13 
				— Doers justified before God  
				- 
				
2 
				Corinthians 7:10–11 — Godly sorrow and diligent change  
				- 
				
Matthew 
				23:25–28 — Warning against outward show  
				- 
				
Acts 2:37–41 
				— Repentance and baptism  
				- 
				
Colossians 
				3:17; Titus 2:11–14 — Zeal for good works in the kingdom  
			 
			
			
			Prepared by Bobby Stafford of the church of Christ at 
			Granby, MO 
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