Sermon session

From Bad To Woes

Session #137 From Bad To Woes

Scripture Matthew 23:13-36

Summary Would a loving and gracious Jesus pronounce a series of woes upon the scribes and Pharisees? Well, that was exactly what He did in Matthew 23:13-36. He had absolutely no choice but to warn them because things had already gone from bad to worse. And Jesus did what He did because He was loving and gracious. Henson takes us through the seven woes and shares seven reminders for kingdom leaders and people.


“But woe to you, scribes and Pharisees, hypocrites! For you shut up the kingdom of heaven against men; for you neither go in yourselves, nor do you allow those who are entering to go in. Woe to you, scribes and Pharisees, hypocrites! For you devour widows’ houses, and for a pretense make long prayers. Therefore you will receive greater condemnation. “Woe to you, scribes and Pharisees, hypocrites! For you travel land and sea to win one proselyte, and when he is won, you make him twice as much a son of hell as yourselves. “Woe to you, blind guides, who say, ‘Whoever swears by the temple, it is nothing; but whoever swears by the gold of the temple, he is obliged to perform it.’ Fools and blind! For which is greater, the gold or the temple that sanctifies the gold? And, ‘Whoever swears by the altar, it is nothing; but whoever swears by the gift that is on it, he is obliged to perform it.’ Fools and blind! For which is greater, the gift or the altar that sanctifies the gift? Therefore he who swears by the altar, swears by it and by all things on it. He who swears by the temple, swears by it and by Him who dwells in it. And he who swears by heaven, swears by the throne of God and by Him who sits on it. “Woe to you, scribes and Pharisees, hypocrites! For you pay tithe of mint and anise and cummin, and have neglected the weightier matters of the law: justice and mercy and faith. These you ought to have done, without leaving the others undone. Blind guides, who strain out a gnat and swallow a camel! “Woe to you, scribes and Pharisees, hypocrites! For you cleanse the outside of the cup and dish, but inside they are full of extortion and self-indulgence. Blind Pharisee, first cleanse the inside of the cup and dish, that the outside of them may be clean also. “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs which indeed appear beautiful outwardly, but inside are full of dead men’s bones and all uncleanness. Even so you also outwardly appear righteous to men, but inside you are full of hypocrisy and lawlessness. “Woe to you, scribes and Pharisees, hypocrites! Because you build the tombs of the prophets and adorn the monuments of the righteous, and say, ‘If we had lived in the days of our fathers, we would not have been partakers with them in the blood of the prophets.’ “Therefore you are witnesses against yourselves that you are sons of those who murdered the prophets. Fill up, then, the measure of your fathers’ guilt. Serpents, brood of vipers! How can you escape the condemnation of hell? Therefore, indeed, I send you prophets, wise men, and scribes: some of them you will kill and crucify, and some of them you will scourge in your synagogues and persecute from city to city, that on you may come all the righteous blood shed on the earth, from the blood of righteous Abel to the blood of Zechariah, son of Berechiah, whom you murdered between the temple and the altar. Assuredly, I say to you, all these things will come upon this generation. Matthew 23:13-36

In this teaching, we examine the series of woes that Jesus pronounced upon the scribes and Pharisees. Jesus did that because He is loving and gracious. He had no choice but to warn them as things had already gone from bad to worse. However, to be fair, not all scribes and Pharisees were wrong or bad. Most, if not all, started out with very good intentions to love, obey and serve God. However, good intentions do not always end up at the right destination. There are enough distractions and deceptions along the way to cause one to veer off track. Good can easily become bad. If not acknowledged and addressed, it can quickly go from bad to worse. We see a recurring theme of irresponsible shepherds and leaders across history of Israel and God’s kingdom where God sent prophets to warn them but they did not heed or repent but went from bad to worse (Ezekiel 34:2, Joshua 1:7-8).

In the 5th Discourse (Matthew 23, 24 & 25), Jesus’ role is clearly that of a prophet – the Prophet of all prophets. Like the prophets who came before Him, He issues warnings. By that time, it had already escalated from bad to worse.

In the previous teaching on Matthew 23:1-12, we explored what leaders are not to do. If not, it will lead to disastrous outcomes and consequences – for both the leader and for those who follow their lead. Jesus goes on in Matthew 23:13-36 to list the issues, pronouncing seven woes (verse 14 is excluded as it was widely agreed that it is not in the original text of Matthew). Woes are not curses but urgent warnings of dire consequences if the state of affairs that are not right, is not promptly addressed.

The Seven Woes

When we compare the the Beatitudes in the first discourse (Matthew 5:3-12) with list of woes in this last discourse, there are at least seven similarities and contrasts:

  • Both describe a state: Blessedness vs Woes
  • Both are about Kingdom of God: Receiving and entering it vs Missing and not entering it
  • Both are about Righteousness: True vs False
  • Both reveal the focus: on others vs self
  • Both end with Persecution: Persecuted for living the kingdom vs Persecution of those who live in the kingdom
  • Both are outcomes of how God’s Word is handled: Right vs Wrong interpretation
  • Both are directed at disciples and multitudes:  Right vs Wrong way

(They have a choice to follow Jesus vs leaders)

Next, the seven woes given in Matthew 23:13-36 follows a chiastic structure: a repetition of similar ideas in reverse pattern as follows:

  • #1 Rejection of the Messiah and His Kingdom (v13)
    • #2 Religious Zeal with Harmful Outcomes (v15)
      • #3 Tradition and Outward Forms (v16-22)
        • #4 Missing the Heart of the Law (v23-24)
      • #5 Tradition and Outward Forms (v25-26)
    • #6 Religious Zeal with Harmful Outcomes (v27-28)
  • #7 Rejection of Messengers of the Kingdom (v29-36)

Reading from #1-2-3; or in reverse, #7-6-5, the passage ends with #4 as the focus and main point. #4 address the key issue which is ‘missing the heart of the Law’ (Matthew 23:23-24).The leaders were more concerned about getting people to tithe than about the heart of the Law – justice, mercy and faithfulness (Micah 6:8, Zechariah 7:9, Hosea 6:6).

Whether contrasted against the Beatitudes or viewed through a chiastic structure, the key issue is about their wrong interpretation of Scripture resulting in them missing the heart of God and the Spirit of the Law. It became a religious system with man-made traditions that was burdensome and legalistic. There was an outward show of religiosity based on questionable motives. Even when confronted by the King and his messengers, they refused to repent as there was too much at stake.

Implications: What can we learn from this?

How about us, the church, the ekklesia – God’s kingdom people? Can we do church and religion; and miss Jesus and the kingdom too?

Heeding Jesus’ warnings through the seven woes, we can draw the following seven key reminders not just for leaders, but for all believers of Jesus Christ:

  • Know the King and embrace the Kingdom.
  • Not just converts but disciples
  • Do not elevate tradition over God’s Word
  • Focus on what truly matters to God
  • Be Consistent Outside and Inside
  • Be Good Examples of the Kingdom
  • Heed Right Prophetic Voices


Understood rightly, woes are not curses. Instead, woes are urgent warnings that things have gone from bad to worse.

When Jesus pronounced these woes, He was not wishing bad upon the religious leaders. On the contrary, He was lovingly and graciously beseeching them, and their followers, to turn and return to Him. And because they would not and did not, it broke His heart as seen through His lament over Jerusalem.

But this teaching is not just for leaders. It was directed to disciples. As people of the kingdom, we must decide how we want to live. Good intentions are not enough. Let us learn from the seven woes and be guided by the seven reminders. We are to always seek to know the heart of our King that we may rightly divide and handle His Word. There is simply no place for pride and complacency or presumption. We are reminded to love the blessings but heed the warnings, hear what the Spirit is saying.  and follow Jesus.