Link Matthew 21:31 to prodigal son?
How does Matthew 21:31 connect with the parable of the prodigal son?

Setting the Scene

Matthew 21:31—“Which of the two did the will of his father?” “The first,” they answered. Jesus said to them, “Truly I tell you, the tax collectors and prostitutes are entering the kingdom of God ahead of you.”

Luke 15:20–24 records the father’s welcome to the prodigal: “While he was still a long way off, his father saw him and was filled with compassion… ‘For this son of mine was dead and is alive again; he was lost and is found.’ ”


Shared Storyline: Two Sons, Two Responses

• In both accounts a father addresses two sons.

• One son initially rebels but later turns, does the father’s will, and is received with joy.

• The other son appears compliant on the surface yet refuses true obedience and fellowship.


Reversal of Expectations

• Jesus shocks His hearers in Matthew 21:31: despised sinners go in first.

• Likewise, the prodigal—socially disgraced—receives robe, ring, and feast ahead of the resentful elder brother.

Isaiah 55:7 echoes the theme: “Let the wicked forsake his way… and He will abundantly pardon.”


Repentance Over Reputation

• The first son (Matthew 21) and the prodigal (Luke 15) both say, “I will go” after realizing their sin.

• Genuine repentance, not a polished past, secures the father’s favor (Psalm 51:17).

• The outwardly obedient brother and the “second son” prove that empty words cannot replace a changed heart (Matthew 15:8).


Warning to the Religious

• Jesus aims Matthew 21:31 at chief priests and elders; the elder brother embodies the same attitude.

Romans 2:4–5 warns that presuming on God’s kindness while harboring hardness stores up wrath.

• The lesson: heritage and rule-keeping do not guarantee kingdom entry—humble surrender does.


Grace Toward the Marginalized

• Tax collectors, prostitutes, and prodigals all illustrate Ephesians 2:13: “But now in Christ Jesus you who once were far away have been brought near by the blood of Christ.”

• Both parables spotlight a father who runs, forgives, and celebrates; grace overrides social standing.


Living the Message

• Examine whether words match actions; say “yes” to God with both lips and life (James 1:22).

• Celebrate every repentant sinner; avoid the elder brother’s coldness (Luke 15:32).

• Rejoice that even late obedience is welcomed—there is still time to “enter the kingdom of God ahead” of those who only pretend.

What actions demonstrate repentance, as seen in Matthew 21:31?
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