Do Prostitutes Go To Heaven? (Matthew 21:28-32)

QUESTIONS: Do Prostitutes Go To Heaven? (Mt 21:28-32). Jesus said to them, “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of heaven ahead of you” (Mt 21:31b).

“The second son said, ‘I go, sir,’ but he went not; and these people do not go. They talk of repenting, but they do not repent. They speak of believing, but they never believe. They think of submitting to God, but they have not submitted themselves to him yet. They say it is time they broke up the fallow ground, and sought the Lord, but they do not seek him. It all ends in a mere promise.” – Charles Spurgeon. Saying versus Doing. Sermon delivered on June 17, 1888, based on Matthew 21:28–32.

“The point of this parable is clear. What matters is living for God, not saying the right words. The religious leaders were good at talking righteous talk, but their stubbornly unrepentant hearts showed that repentant sinners would enter the kingdom before them… These proud religionists should have repented all the more when they saw the notorious sinners repenting, but they did not.” – David Guzik.

Why some “know” the Bible yet don’t know God:

1. They have no sense of the holiness of God, and of God’s love, beauty, power, majesty and awful transcendence (Isa 6:3; Exo 3:5; Rev 4:8; 1 Tim 6:16).
2. They don’t know their own profound unworthiness, wretchedness and sin (Isa 6:4; Mt 5:3; Lk 5:8; 1 Cor 15:9; Eph 3:8; 1 Tim 2:15)–>their false self, never confess, don’t know how to be authentic, fear of appearing weak and vulnerable.
3. They “know” the Bible, but not God [not “heard” God’s “voice”] (Isa 6:8; Lk 5:10).
4. They don’t know God’s grace/unmerited favor (1 Cor 15:10; Eph 2:8-9).
5. God is a boss they [others] must “obey,” but they’re not God’s friend [no relationship with Him] (Jn 15:15).
6. They’re self-deceived and blind and clueless (Jer 17:9; Isa 64:6).
7. They use God for “benefits,” rather than love and serve Him (Mt 6:24).
8. They’re stuck, fixed, rigid, inflexible with rules/tradition (Mt 23:23). Rules and traditions are not necessarily bad. But keeping them faithfully should not cause one to feel superior to or “better” than those who do not keep them, like the “tax collectors and prostitutes.” 

• Before that time: (1) Jesus’ theme and focus is on “the kingdom of heaven“ (Mt 4:17, 23, 9:35): All of Jesus’ parables are about some aspect of “the kingdom of heaven“ (Mt 13:10-11, 18-19, 24, 31, 33, 44, 47). (2) He did not want his messiahship proclaimed (Mt 8:4; 9:30; 12:16; 16:20; 17:9).
• After that time:   (1) He often spoke of his death (Mt 16:21; 17:9, 12, 22-23; 20:18-19, 28; 21:38-39; 26:2).
  • (2) He expressed his messiaship and authority through 3 symbolic actions. (i) As he approached Jerusalem, Jesus is welcomed as the messiah riding on a donkey (Mt 21:5, 9). (ii) Jesus asserts his authority in the temple courts (Mt 21:12-13). (iii) Jesus cursed a fruitless fig tree (Mt 21:19).
  • (3) Jesus rebuked and confronted the religious authorities through 3 polemic parables. (i) The Two Sons (Mt 21:28ff). (ii) The Vineyard/Tenants (Mt 21:33ff). (iii) The Wedding Feast (Mt 22:1ff).

1. R. T. France. The Gospel of Matthew. NICNT (The New International Commentary on the New Testament). 2007. How to interpret the narrative’s organization, given that the original Greek manuscripts lacked modern chapter and verse divisions. Key structural theories:

• The 5 Books Theory (B.W. Bacon): This approach identifies five major teaching discourses in Matthew, each concluded by a specific formula (Mt 7:28, 11:1, 13:53, 19:1, 26:1). While influential, France argues it incorrectly elevates these speeches as the exclusive “skeleton” of the book, ignoring the narrative action.
• Person, Proclamation, and Passion (Kingsbury & Bauer): This theory uses the phrase “From that time Jesus began to” (Mt 4:17, 16:21) to divide the book into 3 sections. While France validates these turning points, he criticizes the model for lumping the final 12 chapters into a single monolithic “passion” block, which flattens the narrative’s complexity.
• The Geographical Framework: France proposes a structure based on geographical progression, mirroring the Gospel of Mark: an extended prologue, a long ministry phase in Galilee, a transition phase during the journey south, & a climactic arrival/rejection in Jerusalem. Unlike modern readers who might see John’s account of multiple trips as contradictory, France suggests Matthew used this simplified geographical arc to build dramatic tension & highlight the conflict between the Galilean prophet & the Jerusalem elite.

Key Takeaways for Interpretation:

• Geopolitical Context: Readers must understand that Galilee and Judea had distinct cultural, economic, and political identities; the conflict was not just religious, but also sociological (a rural outsider challenging a metropolitan establishment).
• Oral Performance: France posits that Matthew was likely designed for communal oral presentation in installments, rather than private silent reading, which would allow listeners to better track the narrative tension over time.
• The Ending: A significant departure from Mark is the triumphant return to Galilee (Mt 28:16-20), which brings the story full circle and launches the messianic mission from the margins rather than the center.

Note: Jericho lay down in the Jordan Valley/Judean desert region. Travelers coming from Jericho to Jerusalem walked an uphill road (climbing roughly 3,000 feet) that passed straight through or past the area of Bethphage and over the summit of the Mount of Olives before descending into Jerusalem.

Under biblical and Jewish law, the tithes (one-10th of produce and crops) given by the Pharisees and other Israelites were designated for the Levites, priests, and the needy (the poor, widows, orphans) to support the religious and social structure of ancient Israel.

The false self. The Pharisees and religious leaders who opposed Jesus were living out a form of a “false self,” characterized by outward piety masking internal corruption, pride, and hypocrisy.