Seven Woes and a Wail

In this scathing yet sorrowful message based on Matthew 23:13–39, Chuck Swindoll analyzes Jesus’ final public sermon before His arrest and crucifixion. Swindoll notes that Jesus leaves the shadows of private ministry to confront the “religious mafia” of His day—the scribes and Pharisees—unloading a series of seven specific judgments upon them [1, 24–25]. Swindoll defines the repeated word “woe” not merely as anger, but as a complex mix of righteous wrath and poignant sorrow, likening it to a faithful spouse discovering decades of betrayal [18–19].

The sermon dissects the seven charges Jesus levels against these leaders, exposing them as “hypocrites” (actors wearing masks). Jesus condemns them for shutting the door to the Kingdom in people’s faces, traveling great distances to make converts who become “twice the child of hell,” and focusing on trivial details (tithes of herbs) while neglecting justice, mercy, and faith [20, 26–30]. Swindoll highlights the vivid imagery Jesus uses, calling them “blind guides” and “whitewashed tombs”—beautiful on the outside but filled with dead men’s bones and filth on the inside. He emphasizes that while humans look at the outward appearance, Jesus, being God, was “in the know” regarding the reality of their hearts.

The message shifts from the “woes” to the “wail”—a lament over Jerusalem. Swindoll describes Jesus’ broken heart as He cries out, wishing to gather the nation like a “mother hen protects her chicks,” yet they refused Him. Swindoll concludes by challenging the listener to drop the mask of hypocrisy, warning that religious activity without a relationship with Christ is futile. He urges the congregation to admit their inner emptiness and accept the exclusive, protective shelter of the Savior before it is too late [47–49, 58–59].

Message Key Facts:

• Definition of “Hypocrite”: Swindoll explains the Greek word hupokrites refers to an actor on a stage who wears a mask to play a part. In the New Testament, it refers to those who pretend to be righteous outwardly while being corrupt inwardly [20–21].
• The “Cat” Illustration: Swindoll opens with a humorous story about a husband who hates his wife’s cat and gets rid of it, then offers a reward because he knows it won’t be found. The point illustrates that “being in the know” changes one’s attitude and confidence. Jesus was “in the know” regarding the Pharisees’ true nature [11–14].
• The Seven Woes: Swindoll categorizes the accusations into specific failures:
  1. Exclusion: Keeping people out of the Kingdom.
  2. Subversion: Making converts into children of hell.
  3. Blind Guidance: Misleading others with distorted priorities.
  4. Majoring in Minors: Obsessing over gnat-sized rules while swallowing camel-sized sins [30–32].
  5. Internal Filth: Cleaning the outside of the cup while leaving the inside full of greed.
  6. Spiritual Contamination: Being like whitewashed tombs (death concealed by beauty).
  7. Murderous Heritage: Building monuments to prophets their ancestors killed, while plotting to kill the Messiah.
• The Mother Hen Imagery: Swindoll uses a story from Donald Barnhouse about a hen found dead after a barnyard fire; under her charred wings were live chicks. This illustrates Christ’s desire to take the judgment (fire) upon Himself to protect His people, if only they would come to Him [50–51].
• The Sword of the Spirit: Connecting the exposure of the Pharisees to Hebrews 4:12, Swindoll notes that God’s Word cuts deeper than a surgeon’s scalpel. While Shakespeare or poetry might make one think, only Scripture can expose the “naked” reality of the soul [35–37].
• The Cadet’s Honesty: Swindoll shares a rare example of anti-hypocrisy involving a cadet at the Air Force Academy who, when asked about his quiet time, admitted to his mentor Laurence Sny, “I don’t have a quiet time… my life is empty.” Swindoll praises this as the honest confession necessary for true change [41–43].
• The Exclusivity of the Gospel: Swindoll addresses the modern resentment toward the claim that Jesus is the only way. He argues that since it is God’s heaven, He has the sovereign right to set the entrance requirements—faith in His Son [52–53, 57].

Message References:

• Matthew 23:13–39: The primary text containing the seven woes to the scribes and Pharisees and the lament over Jerusalem.
• Hebrews 4:12–13: “The word of God is alive and powerful… nothing in all creation is hidden from God. Everything is naked and exposed”.
• Matthew 23:24: “You blind guides! You strain your water so you won’t accidentally swallow a gnat, but you swallow a camel!” [31–32].
• Matthew 23:27: “You are like whitewashed tombs—beautiful on the outside but filled on the inside with dead people’s bones”.
• Matthew 23:37: “Jerusalem, Jerusalem… How often I have wanted to gather your children together as a hen protects her chicks beneath her wings, but you wouldn’t let me”.
• John 14:6: “I am the way, the truth, and the life. No one comes to the Father except through Me”.

Message Speaker:

Pastor Chuck Swindoll